Christmas Markets Connecticut 2025 Top Festive Events and Fairs to Visit

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.