Christmas Markets Connecticut 2025 Top Festive Events and Fairs to Visit

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