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 28, 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.