Christmas Markets Connecticut 2025 Top Festive Events and Fairs to Visit

Christmas markets bring a special kind of magic to Connecticut during the holidays. Towns across the state fill up with local artists, food vendors, and festive entertainment.

Connecticut’s Christmas markets in 2025 offer a wide mix of activities and shopping for holiday gifts. Strolling through these markets, you’ll experience local traditions and enjoy a fun day out with friends or family.

1) Milford Christmas Market

Head to the Milford Christmas Market on the historic Milford town green. This year’s event is set for Friday, November 29, 2025.

Vendors line the walkways with tents for afternoon and evening shopping. Over forty local sellers offer food, crafts, and unique seasonal gifts.

Santa will be there for photos, so it’s a great stop if you’ve got kids in tow. As dusk falls, the tree lighting ceremony kicks off the night.

The market is outdoors and admission is free. It’s right downtown, so grabbing a coffee or bite nearby is easy.

You’ll find paid and street parking close by. If you want to make a weekend of it, check out Hampton Inn Milford or Hyatt Place Milford/New Haven—both are just a short drive away.

For updates, check the official Milford CT Christmas Market event page.

Date	Time	Location	Cost	Where to Stay Nearby	Website
November 29, 2025	Afternoon-Evening	Milford Town Green, Milford, CT	Free	Hampton Inn Milford, Hyatt Place	https://www.facebook.com/events/milford-town-green/milford-ct-christmas-market/903165885109150/

2) Rowayton Community Center Holiday Market

The Rowayton Community Center Holiday Market pops up in early December. It’s usually held in the Potting Shed at 33 Highland Avenue, Rowayton.

Here you’ll discover handmade crafts, holiday decorations, and fresh greenery. The market runs for a few hours in the morning and early afternoon.

Food and drinks are usually for sale if you get hungry. Locals from nearby towns show up every year, making it a real community event.

Parking is simple—just use the community center lot. The vibe is relaxed and friendly, ideal for families or anyone out for a stroll.

There’s no admission fee; you only pay for what you buy. Restrooms are inside the community center if you need them.

Staying overnight? Hotels near Rowayton are easy to find on Booking.com.

Date	Time	Location	Cost	Where to Stay Nearby	Website
December 7	9:00 am – 1:00 pm	33 Highland Avenue, Rowayton, CT	Free admission	See Booking.com	Rowayton Gardeners Christmas Market

3) Bridgeport P.A.L. 74th Annual Christmas Village

The Bridgeport P.A.L. 74th Annual Christmas Village runs from November 30 to December 23. You’ll find it at the Bridgeport PAL Complex, 2 Quarry Road, Trumbull.

This holiday tradition has been going strong for over 70 years. The Christmas Village welcomes visitors daily from 1 p.m. to 8 p.m.

Expect festive music, decorated displays, and a visit from Santa Claus. Kids love it, but honestly, adults get into the spirit too.

Admission? Totally free. Parking’s on-site, so that’s one less thing to worry about.

If you’re coming from out of town, check Booking.com for hotels in Trumbull or the greater Bridgeport area. You’ll find plenty of options, whether you want a hotel or something cozier.

For the latest details, swing by the Bridgeport PAL Facebook page.

Dates	Times	Location	Cost	Where to Stay Nearby	Website
Nov 30–Dec 23, 2025	1–8 p.m.	2 Quarry Rd, Trumbull, CT 06611	Free	Booking.com hotels in Trumbull	Bridgeport PAL Christmas Village

4) Trinity on the Green Christmas Market, New Haven

Trinity on the Green puts on its annual Christmas Market right in downtown New Haven. You’ll find it in the undercroft of the church at 230 Temple Street, usually for a few days in late November.

Browse through handmade crafts, knitwear, jams, cookies, and soups to-go. Local volunteers and artisans make this market happen every year.

The historic church setting gives the whole thing a unique, cozy vibe. People from New Haven and nearby towns come to shop, snack, and enjoy the scene.

Admission is free, and everyone’s welcome. If you’re planning to stay overnight, plenty of hotels are just a short walk away.

Dates	Times	Address	Cost	Where to Stay Nearby	Website
Nov 19–20, 2025 (expected)	9 am–1 pm	230 Temple St, New Haven, CT	Free	Omni New Haven Hotel	https://www.trinitynewhaven.org/the-christmas-market

5) Chester Annual Holiday Market

If you want a taste of a local Connecticut holiday market, Chester’s Annual Holiday Market is as straightforward as it gets. You’ll find it on Main Street in Chester, a small town tucked into the Lower Connecticut River Valley.

The market runs every Sunday from December 1 to December 22, 2024. Vendors set up from 10:00 a.m. to 1:00 p.m., selling handmade gifts, crafts, food, and holiday treats.

This market is friendly, low-key, and easy for anyone to enjoy. Admission is free—just show up and wander.

Compared to bigger city events, Chester’s market feels relaxed and never too crowded. Since it’s outdoors, bundle up if it’s chilly.

Nearby, you’ll find The Bee and Thistle Inn and lots of rentals on booking.com. For more details, check the Chester Sunday Market website; they keep info up to date.

Dates	Times	Location	Cost	Where to Stay Nearby	Website
Dec 1-22, 2024 (Sundays)	10am–1pm	Main St, Chester, CT	Free	Booking.com Chester, CT	Chester Sunday Market

6) New England Christmas Festival

You can check out the New England Christmas Festival at the Earth Expo Center, Mohegan Sun in Uncasville, Connecticut. The event runs from November 7 to November 9, 2025.

Friday and Saturday hours are 9:00 am to 6:00 pm. On Sunday, the festival goes from 9:00 am to 5:00 pm.

The festival draws over 350 American artisans from all over the country. Vendors offer crafts, holiday decorations, jewelry, and specialty foods.

The indoor venue covers 125,000 square feet. That’s a lot of space to wander and discover new booths.

Adult tickets cost between $17 and $22, with possible extra fees at checkout. Kids under 15 get in free with a paying adult.

Parking at Mohegan Sun doesn’t cost anything, so that’s one less thing to worry about. If you want to stay nearby, you can book a room at Mohegan Sun or look for other hotels in Uncasville on booking.com.

For updates, artisan details, and tickets, visit the New England Christmas Festival website.

Dates	Times	Location	Cost	Where to stay	Website
Nov 7-9, 2025	Fri/Sat 9am-6pm; Sun 9am-5pm	Earth Expo Center, Mohegan Sun, Uncasville, CT	$17-$22 (children free)	Hotels in Uncasville	New England Christmas Festival

7) Hartford Winterfair

Hartford Winterfair pops up every year at Union Station in downtown Hartford. This holiday event brings together locals and visitors who want to support small and micro businesses.

You can get there easily by train or bus, since public transportation stops right outside. Over 100 vendors set up shop, selling gifts, crafts, food, and all sorts of seasonal treats.

The market runs on Saturdays and Sundays in December. Usually, you’ll find it open from noon to 5 PM.

Union Station’s historic vibe really adds to the classic holiday feel. All the vendors are inside, so you don’t have to worry about the cold or snow.

Many booths offer products unique to Hartford and nearby towns. Admission is free, which is always nice.

If you’re staying overnight, check out The Goodwin Hotel or the Marriott Hartford Downtown—both are just a short walk from Union Station. For more info, head over to the official Hartford Winterfair site.

Dates	Times	Location Address	Cost	Where to Stay Nearby	Website
Nov 30–Dec 22, 2025 (Sat & Sun)	12 PM–5 PM	Union Station, 1 Union Pl, Hartford, CT	Free	The Goodwin Hotel, Marriott Hartford Downtown	https://www.winterfairhartford.com/

8) Hartford Saengerbund Medieval Christmas Market

If you’re after a traditional German Christmas market in Connecticut, check out the Hartford Saengerbund Medieval Christmas Market. It happens each year at 719 North Mountain Road in Newington.

Inside, you’ll spot stalls with German foods, crafts, ornaments, and gifts. The market tries to capture the feel of a European holiday market—think music, lights, and a little bit of magic.

Kids and adults can wander, eat, and pick up unique handmade goods. The market usually opens in late November, and for 2025, you can expect it near the end of the month.

Keep an eye on their official website for the latest times and updates. Parking’s available at the venue, and you can reach Newington by car from nearby towns.

Need a place to stay? Booking.com lists hotels in Newington and Hartford. The Hartford Saengerbund Medieval Christmas Market gives you a peek at old German holiday traditions.

It’s a good spot for families, couples, or anyone flying solo.

Dates	Times	Location	Cost	Where to stay nearby	Website
Late Nov 2025	Not announced	719 North Mountain Road, Newington, CT 06111	Not announced	Hotels in Newington on booking.com	https://www.hartfordsaengerbund.org/christkindlmarkt/

9) Fairfield County Holiday Markets

Fairfield County hosts a bunch of Christmas markets every year. You’ll find local vendors, handmade gifts, crafts, and tasty seasonal food.

Many markets are indoors, so you can shop without freezing. Stamford’s Christmas in Connecticut Expo at Chelsea Piers is a regular favorite.

This market draws folks looking for crafts, local treats, and fun holiday displays. Families come for unique gifts and the festive vibe.

Newtown’s Holiday Festival Market is another good pick. Vendors there sell crafts, baked goods, and offer entertainment you won’t find in big stores.

Most market spots have parking. Entry is often free, though some activities or snacks might cost a little extra.

Check online for details before you head out. Hotels are close to many venues, and Booking.com can help you find a place in Stamford or Newtown.

Fairfield County’s easy to reach from New York City, so it’s a popular day trip for holiday shoppers.

Date	Time	Address	Cost	Where to Stay (Booking.com)	Website
Dec 7, 2025	11:00 am-4:00 pm	Edmond Town Hall, Newtown, CT	Free	Hotels in Newtown	Newtown Holiday Festival Market
TBA (2025)	TBA	Chelsea Piers, Stamford, CT	TBA	Hotels in Stamford	Christmas in Connecticut – Fairfield County

10) Trumbull Quarry Road Christmas Market

Every year, a Christmas market pops up at 2 Quarry Road in Trumbull, Connecticut. This spot also hosts the Bridgeport P.A.L. Christmas Village, a tradition that’s been going for over 70 years.

When you show up, you’ll see decorated stalls, sparkling lights, and a spot where families meet Santa Claus. Activities usually include photo ops, crafts, and classic seasonal snacks.

The market opens in the afternoon and goes into the evening. For 2025, hours are typically 1:00 PM to 8:00 PM.

Entry is free, though some attractions might charge a small fee. Parking’s available on site.

If you need a hotel, check out the nearby Trumbull Marriott Shelton on booking.com. It’s just a quick drive from Quarry Road.

More details will show up closer to the event on the Bridgeport PAL Christmas Village Facebook page.

Dates (2025)	Times	Location Address	Cost	Where to Stay Nearby	Website Address
TBA	1:00 PM-8:00 PM	2 Quarry Road, Trumbull	Free entry*	Trumbull Marriott Shelton	https://www.facebook.com/BridgeportPALChristmasVillage/
*Some activities may require a fee.

11) Milford handmade ornament vendors

In Milford, you’ll stumble across plenty of Christmas markets and fairs with local handmade ornament vendors. Most events happen indoors, so you get a warm, cozy spot to check out winter crafts.

Local artists and small businesses bring unique ornaments, and you’ll find everything from classic to quirky, modern shapes. The tables are loaded with other stuff, too—crochet bits, books, jewelry, and homey decorations.

Vendors sometimes run raffles or bake sales, so there’s always a reason to wander and see what’s new. The Milford Christmas Market really highlights handmade ornaments and draws in folks searching for a special holiday gift.

Most Milford Christmas fairs pop up in November or early December. You might find them at city halls, schools, or tucked into community centers.

Families and craft collectors turn out, along with anyone just hoping to snag a holiday keepsake. It’s a nice break from big-box shopping, honestly.

Here’s a quick breakdown of one of Milford’s main Christmas markets:

Dates	Times	Location	Cost	Where to Stay Nearby	Website
November 2025	Varies by day	Milford, CT (various community spots)	Free	Book a hotel in Milford	Milford Event Calendar

12) Rowayton community food stalls

Head to the Rowayton Christmas Market and you’ll spot a handful of community food stalls, all run by locals. They usually serve up baked goods, hot drinks, and seasonal treats made right in Rowayton kitchens.

Cookies, cakes, and savory snacks are everywhere. It’s easy to grab a hot chocolate or coffee while you wander.

Sometimes you’ll see homemade jams or little holiday gifts, too. The market sets up in the Rowayton Potting Shed, part of the Rowayton Community Center.

That spot makes it easy to bump into friendly residents and try food made by your hosts. Ask the vendors about their recipes—they’re usually happy to chat.

Buying from these stalls helps support local projects and gardening groups. Plus, you get a taste of Connecticut holiday flavors in a laid-back spot. Not bad, right?

Date	Time	Location Address	Cost	Where to Stay Nearby	Website
Dec 7, 2024	9 am–1 pm	33 Highland Ave, Norwalk, CT 06853	No entry fee	Hotel options near Norwalk	Rowayton Gardeners Christmas Market

13) New Haven handcrafted plants and crafts

If you’re after handmade crafts and plants, New Haven’s got you covered. The annual event at Trinity on the Green is a good place to start—it’s at 230 Temple Street, and you’ll find crafts, plants, and bulbs from local vendors who make everything themselves.

Holiday decorations and gifts here feel genuinely unique. Many sellers bring things you just won’t see in big stores.

The spot sits right downtown, so it’s easy to get to and close to other city sights. Besides Trinity’s event, you can check out a few other New Haven Christmas markets around town.

Most run in late November or December, and you don’t have to pay to get in. Parking’s nearby, and buses will get you pretty close if you don’t want to drive.

Here’s a quick info table:

Dates & Times	Location	Cost	Where to Stay Nearby	Website
Dec 2025 (dates TBD)	230 Temple St, New Haven, CT	Free	Graduate New Haven, Booking.com	https://www.trinitynewhaven.org/the-christmas-market

14) Chester local artisan booths

Drop by the Chester Holiday Market and you’ll spot booths run by local artisans every Sunday in December. These folks bring handmade goods, crafts, and gifts—stuff you just don’t find at chain stores.

The market lines Main Street in Chester, Connecticut. You’ll see jewelry, woodwork, soaps, textiles, and art, all crafted nearby.

Chatting with the makers is half the fun. You get a real sense of each product’s story.

Since it’s outdoors, just bundle up. The crowd’s usually friendly and not overwhelming, so shopping feels relaxed.

If you need a break, there are coffee shops and little eateries close by. You might even find unique gifts and support the local economy at the same time.

Most shoppers love the slower pace compared to big city markets. Honestly, it’s a breath of fresh air.

Dates	Times	Location Address	Cost	Where to Stay Nearby	Website
Dec 1, 8, 15, 22, 2024	10am – 1pm	Main St, Chester, CT 06412	Free	The Griswold Inn, Comfort Inn Old Saybrook, or options on booking.com for Chester, CT area	https://chestersundaymarket.jimdofree.com/holiday-market-info/

15) Bridgeport holiday food vendors

Bridgeport’s holiday markets bring together a bunch of local food vendors every Christmas season. The Nest Arts Factory Holiday Market is set for December 14 at 1720 Fairfield Ave, and you’ll find food from small businesses alongside crafts and handmade gifts.

The First Annual Wintermarkt (December 6-8) is another good pick if you want to try snacks and treats from the area. Foolproof Brewing Company organizes this one—you can catch the details on their Facebook event.

There’s also the Christkindlmarkt at Holy Trinity Greek Orthodox Church, where you’ll find traditional holiday foods and Greek baked goods. This one always feels extra welcoming, especially for families.

Want more info? Check out Christmas Markets Connecticut 2024 for updates.

Dates	Times	Location	Cost	Where to Stay Nearby	Website Address
Dec 6-8, Dec 14, 2025	Check events	1720 Fairfield Ave; Holy Trinity Church	Often free entry	Booking.com – Bridgeport Hotels	Nest Arts Factory

16) Trumbull unique gift stalls

Drop by Trumbull during the holidays and you’ll stumble onto markets packed with unique gift stalls. You’ll see handmade ornaments, jewelry, candles, and local crafts at nearly every turn.

Food vendors set up booths with sweet treats and hot drinks. It’s not just shopping—it’s a bit of a feast, too.

Most years, about 50 vendors show up, so choices for holiday shopping are plentiful. You can chat with the makers and get the story behind their products.

Live music floats through the air, and festive decorations are everywhere. It’s a cozy, cheerful scene that’s hard to resist.

Trumbull’s holiday markets are family friendly and open to all ages. Parking is usually right there or just around the corner, and entry rarely costs more than a few bucks—often it’s free.

Lots of folks come looking for special gifts and end up staying for the atmosphere. It’s just got that local holiday magic.

The Ultimate Holiday Market Guide has more on what to expect. You’ll find things here you just won’t spot in big box stores.

Here’s a quick table with the basics:

Date	Time	Location	Cost	Where to stay nearby	Website
December 2025	To be announced	Trumbull, CT 06611	Usually Free/$5	]Trumbull Marriott Shelton (booking.com)	trulytrumbull.com

17) Milford fine chocolates booths

At the Milford Christmas Market, you’ll find fine chocolates booths run by local vendors. They offer handmade chocolates with both classic and seasonal flavors.

The booths are famous for their custom Milford-branded sweets and treats. You’ll also spot nearby stalls with handmade ornaments and sea glass art—never hurts to look around.

Families from all over come for the market’s laid-back vibe. Tree lightings and Santa visits are regular highlights, and it never feels too crowded.

Some folks just pop by for a couple hours, others make a day of it. Either way, you’ll leave with something sweet.

Here’s what you need to know:

Dates	Times	Location Address	Cost	Where to Stay Nearby	Website Address
Early December*	Varies yearly	Downtown Milford, CT 06460	Free entry	Hyatt Place Milford/New Haven	https://www.facebook.com/milfordchristmasmarket/

*Check the Milford Christmas Market Facebook page for confirmed dates and times.

18) Rowayton garden holiday artisans

The Rowayton Gardeners Christmas Market pops up behind the Rowayton Community Center at the Potting Shed, 33 Highland Avenue. Local artisans bring hand-decorated wreaths, terrariums, and all sorts of seasonal crafts.

You’ll find garden-inspired creations and fresh winter greenery mixed in. People from nearby towns show up for the relaxed atmosphere and well-made decorations.

Vendors really put their skills on display, using natural and local materials. It’s a nice break from the bigger, noisier events.

Families, couples, and solo shoppers wander through the decorated stalls. If you’re after a quieter holiday market, Rowayton’s a good bet.

Here’s a quick rundown of the essentials:

Dates	Times	Location Address	Cost	Where to Stay Nearby	Website Address
December 7, 2025	9:00 AM – 1:00 PM	33 Highland Avenue, Rowayton, CT	Free	Hotels in Rowayton	Rowayton Gardeners Christmas Market

19) Hartford local craftspeople

Head to Hartford during the holiday season and you can meet local craftspeople at Winterfair. This event takes over Union Station’s Great Hall, right in the city center.

Roughly 30 artisans show up each market day, selling handmade ornaments, jewelry, soaps, and woodcrafts. You get to talk with the makers, hear their stories, and buy straight from them.

Winterfair runs from November 30 to December 22, 2025, every Saturday and Sunday from noon to 5 p.m. Walk in anytime—entry is free.

Hotels like Hampton Inn & Suites Hartford and The Goodwin Hotel are a short walk away, both bookable on Booking.com. Details and updates live on the Winterfair website.

Dates	Times	Address	Cost	Nearby Stay (Booking.com)	Website
Nov 30 – Dec 22, 2025	Sat-Sun, 12-5p	Union Station, Hartford, CT	Free	The Goodwin Hotel, Hampton Inn & Suites	https://www.winterfairhartford.com/about

20) New England Festival pop-up boutiques

The New England Christmas Festival brings over 350 pop-up boutiques to Mohegan Sun in Uncasville, Connecticut. Artisans and crafters from all over the country set up shop with handcrafted gifts, decorations, and specialty foods.

It’s a massive event—about 25,000 visitors drop in over three days. You’ll feel the buzz as soon as you walk in.

Here’s the info you’ll want if you’re going:

Dates	Times	Location Address	Cost	Where to Stay Nearby	Website
November 7-9, 2025	Fri-Sat: 9am–6pm; Sun: 9am–5pm	1 Mohegan Sun Boulevard, Uncasville, CT 06382	$17–$22	Mohegan Sun Hotel	New England Christmas Festival

You’ll find both small makers and seasoned artists selling directly to shoppers. If you want a huge selection of American-made goods, this is the spot.

21) Milford custom Milford branded products

At the Milford Christmas market, you’ll see booths with mugs, shirts, and souvenirs all decked out with the city’s name and symbols. These are favorites for both locals and visitors—everyone loves a good keepsake.

Vendors design these products just for the Milford holiday crowd. Sometimes you’ll spot items with local landmarks or the city’s seal, which is a nice touch.

Plenty of folks pick up these custom Milford branded products as gifts or to remember their trip. For more photos and details, check out the Milford Christmas Market Facebook page.

Here’s a table with the basics for Milford’s market:

Dates	Times	Location Address	Cost	Where to Stay Nearby	Website Address
December 2025 (TBA)	Usually afternoon/evening	Downtown Milford Green	Free to attend	Check Milford Hotels	https://www.facebook.com/milfordchristmasmarket/

22) Hartford Breakfast Lunch & Dinner community vendors

Drop by Hartford during the holidays and you’ll stumble into Winterfair inside Union Station’s Great Hall. This Christmas market is run by Breakfast Lunch & Dinner, a Hartford-based group that loves boosting the local scene.

The event pops up over several weekends in December. More than 30 Hartford vendors show up with gifts, food, and crafts—everything made by folks from the community.

Small businesses and local groups get to meet shoppers face to face. It’s one of those places where you can actually talk to the person who made what you’re buying.

The market’s all about supporting local creators. Handmade items, seasonal treats, and art fill the hall.

Some people come to hunt for unique gifts, others just want to back Hartford’s own businesses. Either way, there’s always something unexpected on the tables.

No tickets needed—admission’s free. You can get there by public transit or car, and if you’re thinking about staying overnight, hotels are close by.

Dates	Times	Location	Cost	Where to Stay Nearby	Website
Nov 30 – Dec 22, 2025	Sat-Sun 12-5	Union Station, 1 Union Pl, Hartford, CT	Free	Hilton Hartford	Winterfair Hartford

23) Fairfield County unique holiday stroll markets

If you’re in Fairfield County, holiday stroll markets are everywhere this time of year. Most happen in cute town centers or tucked-away historic sites.

Expect handmade crafts, seasonal food, and plenty for families to do. Some towns host strolls where you wander between shops and market stalls, which is honestly a lot more fun than it sounds.

Stamford’s events at The Palace Theatre always draw a crowd. Sherman and Trumbull both put on gatherings with music, crafts, and food samples—hard to go wrong there.

Sherman Marketplace is a favorite for its New England goods and festive vibe. Meanwhile, Trumbull’s Christmas Village at Bridgeport P.A.L. has turned into a real tradition, especially for families who want that classic holiday feel.

Thinking of checking one out? It’s smart to know the dates ahead of time, so here’s a quick table with the main details.

Date(s)	Time(s)	Address	Cost	Where to Stay Nearby	Website
April 24, 2025 (Stamford)	8:00 PM	Palace Theatre, Stamford	Varies	Stamford Hotels	https://www.fairfieldafterdark.com/holiday-strolls-winter-festivals-going-on-in-and-around-fairfield-county
Dec. 6-22, 2024 (Hope River Farm)	Various	Hope River Farm	Varies	Nearby Hotels	https://www.reddit.com/r/Connecticut/comments/1h2nvdh/holiday_light_shows_and_strolls_in_ct_for_the/
Nov 21-23, 2024 (Fairfield County Markets)	Various	Multiple, Fairfield County	Varies	Fairfield Hotels	https://mofflylifestylemedia.com/upcoming-holiday-markets/
December 2024 (Trumbull)	TBD	2 Quarry Road, Trumbull	Free	Trumbull Hotels	https://www.ctinsider.com/things-to-do/article/holiday-markets-strolls-connecticut-2024-19945683.php
December 2024 (Sherman)	TBD	15 CT-39, New Fairfield	Free	New Fairfield Hotels	https://christmasmarketusa.com/christmas-markets-connecticut-2024/13/

24) Hartford Saengerbund medieval tradition event

The Hartford Saengerbund’s Christmas market is a throwback to medieval times. Every year, the event takes over the Saengerbund clubhouse at 719 North Mountain Road in Newington, Connecticut.

Expect German food, crafts, and live music filling the space. Artisans bring out handmade goods inspired by old European markets.

It’s a family-friendly scene, and everyone’s welcome. The whole atmosphere tries to echo customs from centuries ago—think German holiday traditions, with decorations, food, and music to match.

Visitors often grab authentic sausages, baked treats, and mulled wine. The vibe is festive, a little old-world, and honestly, it’s a nice change from the usual holiday rush.

The 2025 event should happen in late November, with past years falling around November 25-26. Hours usually land in the afternoon and early evening, which is perfect if you want to dodge the morning crowds.

Dates	Times	Location Address	Cost	Where to Stay Nearby	Website Address
Late November	Afternoon-Evening	719 North Mountain Rd, Newington, CT 06111	Usually Free Entry	Homewood Suites by Hilton Hartford	Hartford Saengerbund Christkindlmarkt

25) Christmas Market undercroft of Trinity Church

The Christmas Market fills the undercroft of Trinity on the Green at 230 Temple Street in New Haven. Every year, locals flock here for handmade crafts, plants, bulbs, and holiday gifts.

The market usually lands the week before Thanksgiving. For 2025, it runs November 22 to 24, with a preview party on November 21.

It’s all indoors, so you don’t have to worry about Connecticut weather. Proceeds help restore the historic 1928 Aeolian Skinner pipe organ at Trinity Church, which feels like a good cause if you ask me.

The event always has a warm, community vibe. Local artisans get a chance to shine, and you get to browse without rushing.

The downtown spot puts you close to other New Haven attractions. If you’re staying the night, plenty of hotels are just a quick walk away—booking.com has you covered.

Dates	Times	Location	Cost	Where to Stay Nearby	Website Address
Nov 22–24, 2025	Not listed	230 Temple St, New Haven, CT	Free entry	Hotels via booking.com (downtown nearby)	https://www.trinitynewhaven.org/the-christmas-market

26) Rowayton Highland Avenue market

You can swing by the Rowayton Gardeners annual Christmas Market in Norwalk, Connecticut. The event happens at 33 Highland Avenue, usually inside the Rowayton Community Center.

In 2025, the market takes place on Saturday, December 7, from 9:00 AM to 1:00 PM. Expect a lively crowd and plenty of local energy.

This Christmas market brings together local gifts, holiday plants, and handmade items. Residents and visitors come for the easygoing, seasonal shopping.

The vibe is friendly and community-focused, and you can get there quickly from nearby neighborhoods. Parking’s available right at the venue.

Entry doesn’t cost anything, and you just pay at the vendor tables if you spot something you like. You’ll see classic wreaths, ornaments, and small gifts for friends or family—nothing too over the top, just solid holiday staples.

If you’re thinking about staying overnight, check out hotel options in Norwalk on Booking.com. For updates or more info, the Rowayton Gardeners’ official page has all the details.

Date	Time	Location Address	Cost	Where to Stay Nearby	Website
Dec 7, 2025	9 AM-1 PM	33 Highland Ave, Norwalk, CT 06853	Free	Hotels in Norwalk	Rowayton Gardeners Christmas Market

27) Bridgeport Christmas Village workshops

The Bridgeport Christmas Village hosts special workshops for all ages. You can make simple crafts, meet Santa, and grab festive photos in decorated corners.

Most of the action happens right inside the main village, not far from Santa’s house. The workshops center around easy-to-make holiday items that you can actually finish in a short visit.

Staff help both kids and adults create ornaments, greeting cards, and other holiday crafts. Supplies are included, and you usually don’t need to sign up ahead of time—just show up and jump in.

Bridgeport PAL runs the Christmas Village every year and welcomes families from all over Connecticut. The event happens at 570 Broad Street, Bridgeport, Connecticut.

According to their Facebook page, the village stays open from December 1 through December 23, from 1:00 PM to 8:00 PM.

Dates	Times	Location address	Cost	Where to stay nearby	Website address
Dec 1-23	1:00 PM – 8:00 PM	570 Broad St, Bridgeport, CT 06604	Free entry	Hotels near Bridgeport, CT	Bridgeport PAL Christmas Village

28) Chester Connecticut River holiday fest

Chester holds a Holiday Market every Sunday from December 1 to December 22, 2024. The market runs from 10 a.m. to 1 p.m. on Main Street, right in the heart of Chester, Connecticut.

You get easy access to local shops and restaurants. Local artisans set up with handmade gifts, food, and all sorts of holiday items.

Since the market’s outdoors, you’ll want to dress for the weather—sometimes it’s chilly. It’s a great spot for unique holiday presents or just a relaxed stroll with family and friends.

Public parking sits nearby, and there’s no entry fee. Chester’s small-town vibe along the Connecticut River makes the whole thing easy to explore on foot.

Thinking of staying overnight? You might try “The Griswold Inn” in Essex through Booking.com, or check out other local inns.

For more info, the Chester Holiday Market’s official site has you covered.

Dates	Times	Location	Cost	Where to Stay Nearby	Website
Dec 1–22, 2024 (Sundays)	10am–1pm	Main St, Chester, CT 06412	Free	The Griswold Inn (Essex, CT)	https://chestersundaymarket.jimdofree.com/holiday-market-info/

29) Milford sea glass artwork vendors

The Milford Christmas Market draws in vendors who sell sea glass artwork. Artists gather glass from the Connecticut shoreline and turn it into simple art, jewelry, and ornaments.

Some booths only feature handmade items. You might spot framed pictures, small sculptures, or wearable art made from sea glass—each piece with its own look, depending on what the artist found at the beach.

There’s a nice mix of vendors focused on local crafts and handmade goods. Sealove Designs CT, for example, creates custom artwork from sea glass.

If you’re hoping to snag a sea glass piece, it’s smart to arrive early. The popular stuff tends to go fast.

Many vendors are open to chatting about their process and materials, so you can actually hear the stories behind the work. That personal touch makes the shopping experience feel special.

Dates	Times	Location	Cost	Where to Stay Nearby	Website
Early December*	Varies by year*	Milford Green, Milford, CT 06460	Free admission	Hampton Inn Milford, Red Roof Inn Milford	https://www.facebook.com/milfordchristmasmarket/

*Check the Milford Christmas Market Facebook page for final dates and times.

30) Bridal and gift specialty stalls in New Haven

Holiday gift shopping in New Haven just feels easier. Several specialty stalls pop up at the local Christmas markets, perfect for folks searching for gifts or bridal items.

At markets like The Shops at Yale, you’ll find unique jewelry, handmade crafts, and decor. Some stalls even offer wedding gifts, which is a nice touch if you’ve got a ceremony coming up.

Trinity on the Green’s Christmas Market features crafts, plants, and homemade foods. If you want something off the beaten path, nearby gift shops in New Haven stay open in April and December.

Here’s a table with the basics for a typical bridal and gift shopping trip in New Haven:

Dates	Times	Location Address	Cost	Where to Stay Nearby	Website Address
Nov–Dec weekends	10am–6pm	1022-1044 Chapel St, New Haven	Free entry	Graduate New Haven (booking.com)	theshopsatyale.com/holiday

31) Food and festive drink booths at Rowayton

The Rowayton Christmas market has plenty of food and festive drink booths. You can grab local pastries, savory snacks, and hot drinks like cocoa and cider.

Vendors bake cookies, muffins, and other treats right here in the community. You’ll also see breakfast sandwiches or soups for a quick, warming meal.

The drink booths mix up both non-alcoholic and alcoholic options—mulled wine for adults, sweet punch for kids. Many drinks use ingredients from the area, which adds a nice local flavor.

It’s easy to chat with the folks making your food. Most booths are small, and sellers are usually happy to answer questions or offer tips.

The food and drink area gives you a spot to rest and warm up, either indoors or under tents. Seating can be limited, so if you’re bringing a group, you might want to plan ahead.

Dates	Times	Location Address	Cost	Where to Stay Nearby	Website Address
December 7, 2025	9:00 AM–1:00 PM	33 Highland Avenue, Rowayton, CT	Free entry	Hotels near Rowayton	Rowayton Christmas Market

32) Holiday music performances at Milford Market

At the Milford Christmas Market, you can catch live holiday music while you wander through the event. The Milford Concert Band often takes the stage with festive songs that really set the mood.

They play classic Christmas favorites—think the tunes you know by heart. It’s easy to get swept up in the spirit when everyone’s humming along.

The market happens right on Milford’s town green, which transforms into a lively hub for activities and music. Once the band wraps up, a local DJ usually keeps the holiday vibe going with more tunes.

You’ll get a nice mix of old-school and newer holiday songs as the afternoon turns to evening. That variety keeps things interesting and upbeat.

All these performances happen alongside the shopping and food stalls, so you don’t have to go out of your way to enjoy the music. No ticket required—the entertainment comes with your visit.

The event draws families and folks from all over the area. It’s open and welcoming, with something for just about everyone.

Dates	Times	Location Address	Cost	Where to Stay Nearby	Website
November 2025 (TBA)	TBA	Milford Town Green, Milford, CT	Free	Hotels in Milford	Milford Christmas Market

33) Hartford artisan show Winterfair

You can swing by Hartford Winterfair at Union Station in Hartford. This holiday market packs in more than 100 small and micro local businesses under one roof.

Vendors sell crafts, art, gifts—you name it. Most of them come straight from the Hartford area, so you get a real local vibe.

Winterfair usually runs from late November through December, and 2025 marks its fifth year. The market opens on Saturdays and Sundays from noon to 5 PM.

The crowd isn’t overwhelming, which makes it nice for families or anyone who prefers a laid-back atmosphere. Union Station sits at 1 Union Place, right in downtown Hartford.

Entry is free, so you can just drop by. There’s street parking close by, and public transit stops right at the station.

If you’re planning to stay overnight, check out hotels near Union Station on Booking.com. The Goodwin Hotel and Hilton Hartford are both popular picks.

Want more info or updates? The Hartford’s Holiday Market: Winterfair website lists vendors and event details.

Dates (2025)	Times	Location Address	Cost	Where to Stay Nearby	Website Address
Nov 30 – Dec 22	Sat–Sun 12–5PM	1 Union Place, Hartford, CT 06103	Free	The Goodwin Hotel, Hilton Hartford (booking.com)	https://www.winterfairhartford.com/

34) Traditional crafts at Saengerbund Market

Head to the Saengerbund Christkindlmarkt in Hartford, Connecticut, and you’ll see a strong focus on handmade crafts. Artisans set up booths to show off their creations—think wooden toys, carved ornaments, and classic nutcrackers.

A lot of the crafts stick to German traditions, which gives the market its unique flavor. People come from all over for special decorations and gifts you won’t spot anywhere else.

Booths also feature knitted scarves, candles, and holiday tableware. You can chat with the artists, ask about their process, or even catch a live demo if you’re lucky.

Most of these crafts aren’t the kind you’d find in a regular store. Buying here means you’re supporting local makers and picking up something one-of-a-kind.

The market also serves up German food and live Christmas music, which really rounds out the festive mood. Here’s a quick look at the details:

Dates (2025)	Times	Location Address	Cost	Where to Stay Nearby	Website Address
To be announced	Usually weekends in December	719 North Mountain Road, Newington, CT 06111	Usually free entry	Nearby hotels	hartfordsaengerbund.org/christkindlmarkt

35) Family-friendly activities at Bridgeport Christmas Village

Bridgeport Christmas Village is all about families and kids. Children under 3 get in free, and everyone else pays a small fee at the door—makes it easy on the wallet.

The kids can dive into egg coloring, cupcake decorating, and simple arts and crafts. The activities use basic materials and are hands-on, so little ones stay busy.

For a few extra bucks, you can snap a photo with the Easter Bunny. The event runs indoors, so weather isn’t a worry, and there’s plenty of space for kids to play while parents relax.

Staff and volunteers keep things moving smoothly. Local treats and food vendors usually set up inside, and there are spots to sit and take a breather if you need it.

If you want more info, the Bridgeport PAL Christmas Village Facebook page posts updates and details.

Dates	Times	Location Address	Cost	Nearby Stays	Website
December (TBA)	TBA	7 Quarry Road, Bridgeport, CT	$2 per person (under 3 free); $10 for Easter Bunny photo	Bridgeport hotels	https://www.facebook.com/BridgeportPALChristmasVillage/

36) Local chocolate makers at Milford Market

When you show up at the Milford Christmas Market, you’ll spot local chocolate makers handing out handcrafted treats. MELT Chocolatier stands out—a Milford-based business making hand-dipped truffles and confections with choice ingredients.

You might catch Meredith from MELT right there, making chocolates on-site. Her fresh truffles and small-batch sweets always draw a crowd, whether you’re hunting for a gift or just want a quick snack.

MELT is a highlight among the artisan food vendors at the market. Their careful, local approach really sets them apart.

Picking up something from a local chocolatier supports small businesses—a big part of what makes the market special. Here’s what you need to know if you’re planning a visit:

Date(s)	Time	Location	Cost	Where to Stay Nearby	Website
December 2025*	Usually 10am–4pm**	Milford Green, Milford, CT 06460	Free	Hyatt Place Milford / New Haven (booking.com)	https://meltchocolatier.com

*Check official listings for exact dates.
**Hours may change; confirm before visiting.

37) Custom ornament crafting in New Haven

In New Haven, you’ll find chances to make your own custom Christmas ornaments every year at the Christmas Market at Trinity on the Green. Local artisans lead workshops where you can design and personalize your own holiday decorations.

The market is indoors at 230 Temple Street, so you don’t have to worry about the weather. Both locals and visitors show up to try their hand at crafting and to browse handmade items.

You get to take home a personalized keepsake, often using simple materials like wood or glass. Vendors also sell ready-made ornaments, including New Haven and Connecticut-themed pieces.

Many let you add names or dates for that extra personal touch. These workshops work for families or solo visitors—no special skills required, and most materials are right there for you.

The vibe is relaxed and creative, and you get a little window into local holiday traditions. Here’s a quick table to help you plan:

Dates	Times	Location	Cost	Where to stay nearby	Website address
December 2025*	TBA	230 Temple St, New Haven	Free entry	New Haven Hotel	https://www.trinitynewhaven.org/the-christmas-market

*Dates will be announced later in the year. For updates, check the Trinity on the Green Christmas Market website.

38) Artisan jewelry at Rowayton Market

Rowayton Market features artisan jewelry vendors with handmade pieces that are anything but generic. You’ll see necklaces, bracelets, earrings, and rings—all crafted by local artists with their own personal style.

Some use silver, some use glass beads or natural stones. Many pieces are one-of-a-kind, so if you’re looking for a standout gift, you’ll probably find it here.

Shoppers often chat with the artists about their process or the story behind a particular piece. That personal touch makes the whole experience a bit more memorable.

The Rowayton Market happens at the Rowayton Community Center on December 7, from 9:00 a.m. to 1:00 p.m. You’ll find it at 33 Highland Avenue, Rowayton.

For details, check out the Rowayton Christmas Market website. Here’s a quick info table:

Date	Time	Location	Cost	Where to Stay Nearby	Website
December 7	9:00 AM–1:00 PM	33 Highland Ave, Rowayton, CT	Free Entry	Hotels in Rowayton	Market Details

39) Seasonal produce stalls at Chester Holiday Market

When you swing by Chester Holiday Market, you’ll spot plenty of stalls overflowing with fresh, local produce. Vendors haul in apples, squash, root veggies, and festive wreaths straight from nearby farms.

Farmers restock their stalls all through December. You’ll usually find the produce crisp, seasonal, and ready for winter meals or holiday recipes.

Locals browse for ingredients and chat with vendors, who sometimes share tips for traditional holiday dishes. Arrive early if you want the best picks—Sundays can get crowded fast.

People come for both gifts and groceries, making the place lively each weekend. Here’s a quick table with the basics:

Dates	Times	Location	Cost	Where to Stay Nearby	Website
Dec 1 – Dec 22, 2024 (Sundays)	10am–1pm	Main St, Chester, CT 06412, United States	Free	Chester, CT hotels	Chester Holiday Market Info

40) Handmade wooden toys in Fairfield County Markets

Handmade wooden toys pop up at several Christmas markets around Fairfield County from mid-November through December. Local artists and craftspeople set up shop with wooden trains, cars, and puzzles—honestly, they’re charming for both kids and collectors.

These artisans carve, sand, and paint each toy by hand, sticking to traditional methods and safe materials. Some even offer custom engraving or little personal touches if you ask during market hours.

If you’re hunting for these unique toys, check out events with art and craft booths. Holiday markets in Fairfield County feature original crafts and woodwork, plus plenty of knitted goods, ceramics, ornaments, and jewelry.

Here’s a quick look at one typical market:

Dates	Times	Location Address	Cost	Where to Stay Nearby	Website
Dec 6–8, 2025	10am–5pm	Fairfield, CT	Free Entry	Hotels in Fairfield	https://mofflylifestylemedia.com/upcoming-holiday-markets/

41) Vintage holiday decor at New England Christmas Festival

The New England Christmas Festival bursts with handcrafted holiday decor and gifts. It’s indoors (thank goodness), so weather won’t slow you down. The festival happens in Massachusetts, but you’ll meet plenty of visitors from Connecticut and other states.

Local artisans offer all sorts of vintage holiday items. Expect to see hand-carved ornaments, old-school garlands, and wreaths made from real greenery.

Booths also show off tableware, wooden decorations, and antique-inspired pieces. The Barn & Mill Gallery stands out—they craft home decor from salvaged wood and barn beams, giving spaces a cozy, rustic vibe.

If you’re after classic decor instead of mass-produced stuff, this place is your jam. You might stumble on custom pieces that fit older holiday themes, too.

Date	Time	Location	Cost (General Admission)	Hotels Nearby (Booking.com)	Website
Nov 7-9, 2025*	Fri-Sun, hours TBA	415 Summer St, Boston, MA 02210	TBA	YOTEL Boston	New England Christmas Festival

*Dates based on most recent event schedule. Confirm closer to 2025.

42) Fairfield County wreath makers

Fairfield County comes alive with holiday wreath makers during Christmas. Shops and markets show off handmade wreaths with fresh greens and ornaments. Some events, like Flurry Fest, highlight festive arrangements—plus crafts and gifts galore.

In towns like Weston, you’ll find wreath workshops where you can get your hands dirty and make your own. Materials and instructions are usually rolled into the workshop price.

Local markets sell both finished wreaths and supplies if you’d rather tackle a project at home. Designs range from classic to quirky, so there’s something for every taste.

For current event times and places, check out sites listing upcoming holiday markets in Fairfield County. Schedules can shift year to year.

Date	Time	Location Address	Cost	Where to Stay	Website
December 7	12:00–6:00 PM	Arch in Bloom, Fairfield CT	Varies by event	Nearby hotels	https://mofflylifestylemedia.com/upcoming-holiday-markets/

43) Gourmet baked goods at Bridgeport Market

Bridgeport Market is a sweet spot for gourmet baked goods from local bakers. You’ll see cookies, breads, cakes, and pastries—some made from family recipes you won’t find anywhere else.

Most booths let you sample before you buy, which is always a win. Some stands offer gluten-free or vegan options, and you can grab hot cocoa or coffee nearby.

The market buzzes during peak hours, and popular treats disappear fast. If you want the best selection, come early or check the schedule.

Bakers display their goods with ingredient labels and prices, so you know what you’re getting. Sometimes you can even watch them decorate treats right at their stalls.

Here’s what you need to know if you want to visit:

Date(s)	Time	Location	Cost	Nearby Stay	Website Address
Dec 6-8, 2025*	10am-6pm	Downtown Bridgeport, CT	Free entry	Holiday Inn Bridgeport	https://allevents.in/bridgeport/christmas-markets-and-fairs

*Dates are based on previous years and may change. Check the Bridgeport Market official listing for updates.

44) Interactive kids crafts in Rowayton

Rowayton hosts hands-on craft activities just for kids during the holidays. Little ones can make their own ornaments, cards, or simple decorations at family-friendly stations—materials are usually included.

These craft times often happen during community markets or special events from local groups. The Rowayton Gardeners have held a Christmas Market in the past, with craft tables and a peek at local traditions.

Activities change each year, but there’s always something for different age groups. Volunteers help guide the projects, especially for younger kids.

Most crafts happen indoors or in sheltered spaces, so weather isn’t a worry. It’s a relaxed spot where kids can try new things and take home a handmade souvenir.

Events are usually free or ask for a small donation. You’ll find them at places like the Rowayton Community Center. For updates, check the Rowayton Gardeners’ website.

Date	Time	Location Address	Cost	Where to Stay Nearby	Website
Usually early December (check current year)	Varies	Rowayton Community Center, 33 Highland Ave, Rowayton, CT	Free or small donation	Book hotels in Norwalk on Booking.com	https://rowaytongardeners.org/kids-events/

45) New Haven potted plants market

If you’re into potted plants for the holidays, New Haven’s Christmas Market at Trinity on the Green is worth a visit. It’s at 230 Temple Street, and you’ll find potted flowers, bulbs, and plant-themed gifts—honestly, they make pretty unique presents. You’ll also see handmade crafts mixed in with the greenery.

The whole thing is indoors, so you can browse comfortably. Regulars enjoy the laid-back vibe and chatting with local vendors. There are also simple decorations and baked goods if you’re in the mood.

The market usually runs for one weekend in December. Entry is free, and there are hotels nearby if you want to stay overnight. For more info, check out the official Christmas Market page.

Dates	Times	Location	Cost	Where to Stay Nearby (Booking.com)	Website Address
Early December	10am–4pm	230 Temple St, New Haven	Free	Omni New Haven Hotel at Yale	https://www.trinitynewhaven.org/the-christmas-market

46) Milford holiday candle makers

If you swing by the Milford Christmas Market, you’ll spot candle makers with a wild range of handcrafted candles. They set up shop right on the Milford Green, which is basically the heart of town.

Local artisans bring candles in all sorts of shapes, scents, and colors. These are perfect for gifts or just sprucing up your home.

You can chat with the folks who actually make the candles. Many use soy or beeswax, and you’ll catch a whiff of holiday scents like pine or cinnamon in the air.

Some makers even run small workshops so you can get a peek into the candle-making process. If you’re curious or just want to try something new, it’s worth stopping by.

The market’s a solid spot if you’re after something unique. Each candle looks or smells a bit different since they’re not cranked out in a factory.

Other holiday goodies are usually nearby too—think ornaments, baked treats, the works. It’s worth a stroll, especially if you like discovering small surprises.

The Milford Green Christmas Market pops up every year, usually in late November. For the latest details, check the Milford, CT Christmas Market Facebook page.

Dates	Times	Location Address	Cost	Where to Stay Nearby (booking.com)	Website Address
November 29, 2025	TBA	Milford Green, Milford, CT 06460	Free	Places to stay nearby	https://www.facebook.com/milfordchristmasmarket/

47) Specialty cheeses at Hartford Winterfair

If cheese is your thing, Hartford Winterfair is a fun stop for unique picks from Connecticut and New England. Local cheesemakers line up with their specialty cheeses, letting you sample flavors and talk about their craft.

They’re pretty open to questions, so don’t be shy. You’ll find cheeses made from cow, goat, and sheep milk—fresh, aged, soft, you name it.

Some of these cheeses only come from tiny farms and you won’t see them in big stores. The fair happens inside Hartford Union Station, which means you stay warm no matter the weather.

It’s easy to grab a wedge to take home or wrap up as a gift. There’s usually other food and drinks going on too, so you can make an afternoon of it.

Dates	Times	Location Address	Cost	Where to Stay Nearby (Booking.com)	Website
Nov 30–Dec 22, 2025 (Sat & Sun)	12–5 pm	Hartford Union Station, 1 Union Pl, Hartford, CT	Free Entry	Nearby hotels	Winterfair’s website

48) Trumbull artisan soap vendors

On the hunt for handmade soaps? Trumbull’s holiday markets have you covered with local vendors offering small-batch options.

Most soaps use simple ingredients and come in scents you probably won’t find anywhere else. Vendors are around to chat about their process and let you try samples.

You’ll spot these soap makers at seasonal Trumbull events. Some markets bring together up to 50 local creators with body care, gifts, and holiday stuff.

The scene is pretty relaxed—just people showing their work and what they’ve got for sale. If you want to pick out a gift, it’s easy since you can talk right to the person who made it.

Soap stalls are usually near other craft and food vendors, so you can browse a little of everything. Carolers, hot drinks, and food trucks often set the mood nearby.

For more info on Trumbull’s holiday markets, check out The Ultimate Holiday Market Guide at Truly Trumbull.

Dates	Times	Location Address	Cost	Where to Stay Nearby (Booking.com)	Website
November-December*	Varies*	5866 Main Street, Trumbull, CT	Free	Trumbull Marriott Shelton	https://trulytrumbull.com/we-love-trumbull/the-ultimate-holiday-market-guide/

*Dates and times can change each year. Always double-check event pages for the latest info.

49) Chester winter pottery displays

Head to Chester during the holidays and you’ll find local pottery displays at the town’s annual market. Artisans line Main Street with tables full of their work.

They focus on seasonal pieces—mugs, bowls, small gifts—usually decorated with winter themes. The pottery event is part of the regular Chester Holiday Market, running every Sunday from December 1 to December 22, 2024.

The hours are 10 a.m. to 1 p.m. As you browse, you can talk with Connecticut potters about their craft.

Many sell directly, so you can ask about designs or glazing if you’re interested. Items range from useful kitchen stuff to tiny decorative figures.

The Chester Holiday Market doesn’t charge to get in. It’s on Main Street, Chester, CT 06412.

If you’re staying overnight, there are local inns and more options on booking.com. For more details, check the market’s official website.

Dates	Times	Address	Cost	Where to Stay Nearby	Website
Dec 1–22, 2024 (Sundays)	10am–1pm	Main St, Chester, CT	Free	booking.com	https://chestersundaymarket.jimdofree.com/holiday-market-info/

50) New England festive wreath workshops

Connecticut has Christmas wreath workshops if you want to make your own holiday decor. Local businesses host these, supplying materials and step-by-step help right there.

They’re pretty popular, running through late November and December. For 2025, Guilford and Cheshire both offer hands-on wreath workshops.

No crafting experience needed—just show up and have fun. All ages can join, and you’ll leave with a finished wreath for your door or table.

Groups are usually small, so you get plenty of help. Dates and times change depending on the workshop, so you’ve got choices.

Many spots even offer snacks or drinks during class. Here’s a quick look at two of the most popular wreath workshops in Connecticut:

Date	Time	Location Address	Cost	Where to Stay Nearby	Website
December 7, 2024	Varies	The Green Petal, Cheshire, CT	Varies	Cheshire hotels	Event details
December 2025 (TBA)	TBA	Guilford, CT (venue TBA)	Varies	Guilford hotels	Event details

What to Expect at Christmas Markets in Connecticut

Connecticut’s Christmas markets? There’s a lot going on. You’ll see holiday lights, taste seasonal foods, and browse gifts from local artists.

Atmosphere and Festive Activities

Most Christmas markets here are outdoors or inside halls decked out with decorations. You’ll walk past stalls strung with lights and ornaments.

At bigger spots like the Saybrook Point Christmas Village in Old Saybrook, there are full-on displays of Christmas lights and holiday scenes. Live music is almost guaranteed—choirs, jazz, even the occasional solo act.

Some places offer carriage rides or interactive events for families. Holiday strolls let you wander through downtowns lined with decorations and evening events.

You might bump into Santa or catch an ice sculpture demo if you’re lucky. A lot of these events run weekends in December.

Entry is usually free, but some special stuff costs extra. Even small towns like Norwich get in on the fun, and honestly, the local traditions bring a cozy, festive feeling you can’t fake.

Shopping here supports small businesses and local groups, which is always a plus.

Seasonal Food and Local Artisans

Food really shapes the Connecticut Christmas market scene. Vendors serve up warm apple cider, holiday cookies, and pretzels.

Some markets throw in light meals—think bratwurst, hot chocolate, and local baked treats. These snacks bring out those classic Christmas flavors you crave.

Local artists and crafters show off their work at many markets. You’ll find jewelry, ornaments, soaps, and woodwork, all made by folks from Connecticut.

Sometimes you get to chat with the artists themselves about what inspires them. These markets let you pick up gifts you just won’t see in chain stores.

Most of the goods come from small businesses. Buying here keeps your money local and the quality feels genuine.

During the holidays, towns put their artists and chefs in the spotlight—check out the Bristol Bazaar or other year-round spots. You can shop, snack, and bring home pieces that really capture New England’s vibe.

Tips for Visiting Connecticut Christmas Markets

You’ll get the most out of Connecticut Christmas markets if you plan ahead and know how to get around. A little prep can save you stress and time, especially if you know what practical details to expect.

Planning Your Visit

Most Christmas markets in Connecticut run from late November through December. You’ll come across unique gifts, local crafts, and festive eats.

Try to arrive early—parking fills up fast and crowds can get thick. Some markets are outdoors, so dress for the cold or possible rain.

Bring cash. Not every vendor takes cards, and having small bills or coins makes life easier.

Be sure to check if pets are allowed before you go. Strollers are fine at most places, though you might have to squeeze through busy aisles.

It’s smart to check the event website for last-minute updates, especially if the weather’s looking rough.

Accessibility and Transportation

Parking fills up fast, especially on weekends. Try to get there close to opening if you want a spot. Many markets have free or paid lots nearby, but they do fill quickly.

You can usually reach the bigger Christmas markets by local bus or ride-share. Honestly, public transit can save you a headache during busy times.

Most venues have sidewalk ramps and accessible restrooms, but it really depends on the place. If you need extra accommodations, it’s smart to contact the event in advance and double-check. Crowds pick up by mid-day, so mornings are a safer bet if you want more space to move around.

If you’re coming in from out of town, hotels like the Hilton Hartford or Mystic Marriott are just a short drive away. Some markets run shuttle buses or provide details about drop-off zones, but not all do. Watch out for street closures—they can throw off your plans in a hurry.