Christmas Markets Connecticut 2025 Top Festive Events and Fairs to Visit

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/