Christmas Markets Massachusetts 2025: Best Festive Events and Holiday Fairs

41) Holyoke Holiday Market

If you’re after a classic holiday shopping vibe in western Massachusetts, check out the Holyoke Holiday Market. They run it each year as a fundraiser for the Holyoke Merry Go Round, and it’s a great way for the community to come together and support small businesses.

You’ll see vendors selling seasonal gifts, crafts, and food. The market has a warm, welcoming feel, with local music and family activities popping up during the event.

This one usually happens in December. In 2024, the Wistariahurst Museum hosted a similar event on December 8 from 11 am to 3 pm.

Dates for 2025 will probably land in early December again. The Holyoke Holiday Market keeps a presence on Facebook, so you can check there for updates.

Date	Time	Address	Cost	Nearby Stays (Booking.com)	Website
Early Dec. 2025 (est.)	TBA	Holyoke, MA (Check event page)	Usually free	Holyoke hotels	Holyoke Holiday Market Facebook

42) South Boston Holiday Market

The South Boston Holiday Market sets up each winter at 100 Seaport Boulevard in Boston. It’s an outdoor market with plenty of booths selling crafts, food, and gifts.

Locals and tourists both show up for seasonal items near downtown. You can hop off public transit nearby, which is handy if you want to skip parking headaches.

Most people wander through in under an hour, at least according to past guests. Many stalls offer similar goods, so expect a familiar selection if you’ve visited before.

Want to skip the entry lines? Reserve a timed ticket with the Seaport Insider app and get a thirty-minute window for entry. Check ticket options and details on the Seaport Holiday Market website.

Plenty of hotels are within walking distance, and you can find them easily on Booking.com. Market dates usually run from late November through December, but times can change year to year—always check before you go.

Dates	Times	Location	Entry Cost	Where to Stay Nearby	Website Address
Late Nov–Dec (2025)	Varies	100 Seaport Blvd, Boston	May apply	View hotels on Booking.com	https://www.bostonseaport.xyz/holidaymarket

43) Chelmsford Holiday Market

The Chelmsford Holiday Market happens every year in Chelmsford, Massachusetts. It brings together the community for holiday shopping, festive activities, and food.

You’ll spot craft booths, local vendors, and holiday decorations everywhere. The 2025 market is set for early December in the Chelmsford Town Center and Common.

During the event, you can catch tree lighting, face painting, hayrides, music, and snacks. The Holiday Market draws both locals and folks from neighboring towns.

It’s a relaxed, family-friendly environment. The event usually runs about two hours, from late afternoon into early evening.

Admission is free and all ages are welcome. Parking is available near the Town Center.

If you want to stay overnight, the Radisson Hotel Chelmsford-Lowell is close by and a favorite with visitors. For more details and updates, check the official Chelmsford events page.

Dates	Times	Location Address	Cost	Where to Stay Nearby	Website Address
Early December	4-6 PM	Chelmsford Town Common, Chelmsford, MA	Free	Radisson Hotel Chelmsford-Lowell	https://www.chelmsfordma.gov/94/Events

44) Brockton Christmas Market

If you’re in Massachusetts during December, consider checking out the Brockton Christmas Market. Local vendors, food stands, and handmade crafts fill the event, usually right in the center of Brockton.

Holiday decorations and seasonal music set the mood. Most stalls offer gifts, ornaments, and baked treats.

The event welcomes families and attracts people from nearby towns. You can drive or take public transport—parking is close but fills up fast on weekends.

For the latest details and schedules, visit Brockton Christmas Markets and Fairs. Need a place to stay? Try the Holiday Inn Express Brockton or Hampton Inn Brockton, both easy to book on Booking.com.

Dates	Times	Location Address	Cost	Where to Stay Nearby	Website Address
December 2025*	Usually 11am–5pm*	Downtown Brockton, MA	Free entry	Holiday Inn Express, Hampton Inn	https://allevents.in/brockton/christmas-markets-and-fairs

*Dates and times may change. Always check the event website for updates.

45) Dennis Holiday Artisan Market

The Dennis Holiday Artisan Market is a seasonal event in Dennis, Massachusetts. Local artists and makers sell handcrafted goods—think ornaments, jewelry, candles, and more.

You get the chance to find gifts that are unique and made right in the region. The market is usually indoors, often at a community center or similar public spot.

Parking is nearby, and the market feels welcoming for families. You’ll see both residents and out-of-towners browsing together.

Plan your visit around other holiday happenings in the area, like craft fairs or village strolls. For updates on schedules or new events, check the Dennis Chamber of Commerce event calendar.

Dates	Times	Location Address	Cost	Where to Stay (Booking.com)	Website Address
December TBA	TBA	Dennis, MA (check calendar)	Free to low	Hotels near Dennis, MA	https://business.dennischamber.com/calendar

46) Gloucester Winter Festival Market

The Gloucester Winter Festival Market sets up in December at The Cut, a local spot in Gloucester, Massachusetts. The market opens December 15 from 11 a.m. to 4 p.m.

Vendors bring crafts, gifts, and holiday foods. Local makers showcase their work, and you can browse or buy as you like.

Crowds aren’t usually overwhelming, so moving around feels easy. The market is indoors, which is a relief if it’s cold or snowy outside.

Decorations include lights and seasonal displays. The location is central, so shops and restaurants are close if you want to explore more.

If you’re staying overnight, find a hotel near Gloucester on Booking.com.

Dates	Times	Location	Cost	Where to Stay Nearby	Website Address
December 15, 2025	11 a.m.–4 p.m.	The Cut, 177 Main St, Gloucester, MA	Free	Hotels near Gloucester on Booking.com	https://www.nshoremag.com/shop-renew/holiday-shopping-nights-strolls-and-markets-on-the-north-shore/

47) Cambridge Glass Holiday Market

The Cambridge Glass Holiday Market pops up every December in Cambridge, Massachusetts. You’ll find it near Harvard Square, tucked close to the shops and public transit.

Local glass artists show off their work here, focusing on hand-blown ornaments and seasonal crafts. You can catch glassblowing demonstrations right at the market.

Vendors bring glass jewelry, vases, and all sorts of small holiday decorations. Folks usually come looking for unique, locally made gifts—something with a bit of heart.

The vibe stays relaxed, especially on weekday evenings when crowds are easier to handle. Weekends get a little busier, with more families and groups wandering through.

Holiday music drifts through the air, and a few stalls serve up warm drinks if you need to thaw out. Here’s a table to help you plan your visit:

Dates	Times	Location Address	Cost	Where to Stay Nearby	Website
December 10–15 & 17–22, 2025	12:00 PM–7:00 PM	1426 Massachusetts Ave, Cambridge, MA 02138	Free entry	Harvard Square Hotels	Cambridge Glass Holiday Market

48) Newbury Holiday Christmas Market

The Newbury Holiday Christmas Market sets up in Boston’s Back Bay. It mixes a bit of traditional European holiday flair with New England craft fair style.

Artisans and small businesses fill booths along Newbury Street and nearby spots, showing off handmade gifts. You’ll find crafts, ornaments, candles, winter gear, and plenty of local food.

The whole place feels lively, strung with holiday lights and decorations. Sometimes you’ll catch carolers or street performers—it depends on the day.

Vendors come and go, so what you see can change from one weekend to the next. Shops in the area usually stay open later for the market, which is nice if you prefer to stroll in the evening.

Staying nearby is easy, with places like Newbury Guest House right in the neighborhood. You’re close to transit and most things are walkable.

Here’s a table with the basics if you’re thinking of visiting:

Dates	Times	Location	Cost	Where to Stay	Website
November–December 2025	Varies, evenings	Newbury St, Boston, MA 02116	Free entry	Newbury Guest House (booking.com)	https://www.newburyguesthouse.com/about/blog/back-bay-boston-holiday-wonderland

49) Salem Arts Holiday Market

If you’re in Massachusetts during winter, the Salem Arts Holiday Market is worth checking out. The Salem Arts Association puts this one together, and it’s got a mix of handmade art, jewelry, and crafts—all by local artists.

The setup feels pretty local, with a focus on quality artisan products. You’ll spot holiday gifts, decorations, and maybe even get to chat with some of the artists.

Live music often adds to the scene, but it never really gets too loud or chaotic. The event usually happens in December right in central Salem.

Admission won’t cost you anything, so you can just pop by if you’re in the area. Out-of-towners can book a room at a nearby hotel, which is handy.

Here’s a table with the details:

Dates	Times	Location Address	Cost	Where to Stay Nearby	Website
December (check website)	Varies	159 Derby St, Salem, MA 01970	Free	Hotel Salem	Salem Arts Holiday Market

50) Everett Winter Holiday Market

The Everett Winter Holiday Market pops up every December in Everett, Massachusetts. You’ll find holiday crafts, seasonal treats, and all sorts of small gifts here.

Local vendors set up booths with handmade goods and unique products. There’s a cozy vibe, thanks to music and simple decorations scattered around.

The market usually happens at a familiar community center or some public spot everyone knows. Kids can jump into family activities and, of course, grab a quick visit with Santa if they’re lucky.

Folks from around Everett come by to shop, snack, and just hang out together. Getting there’s a breeze—drive in or hop on public transit.

Vendors mostly take both cash and cards, which makes things easier. Here’s a quick table to help you plan:

Dates	Times	Location Address	Cost	Where to Stay Nearby	Website
Early December, 2025 (exact date TBA)	11 am – 5 pm	90 Chelsea St, Everett, MA 02149	Free	Stay in Everett	Everett Community Events

Want updates for 2025? Keep an eye on the city’s official website.