The best holiday and Christmas markets in Boston to enjoy this winter

A rotating lineup of diverse vendors are popping up all season in Downtown Crossing. Presented by the Downtown Boston Alliance of businesses, the Downtown Boston Holiday Market happens (weather-permitting) on Summer Street Plaza every Thursday, Friday and Saturday from 11am–4 pm from November 29 to December 22. Keep your eyes peeled for carolers and other celebrations, as well.

The Seaport cosplays Christmastime in Europe—with a benevolent yeti. A pop-up marketplace, iceless curling rink, photo backdrop and food hall from developer-organizers WS, Snowport spans a city block in the Seaport and attracted 1 million visitors in 2023. (There's a new way to skip the lines on weekends this year!) The annual tree lighting is on December 6 and holiday festivities continue through Sunday, Dec. 29. The iceless curling lanes brighten up winter in the Seaport with free outdoor fun open through February.

This creative and collaborative hub in Somerville offers a year-round, local, artisan shopping experience, along with delicious eats—but for the holiday season, they’ll also be featuring special events such as Black Friday sales, Small Business Saturday, a winter night market, holiday stroll and much more. Check the website for details about its full seasonal schedule.

Can’t get enough holiday wonder? Winter Fest is just what you need. From the creative minds behind Boston’s Wicked Haunt Fest, Winter Fest debuts on December 6 at Hood Park in Charlestown. Time Out got a first look at the winter wonderland of light displays and the Après Ski Veuve Clicquot Gondola Lounge. There will also be a holiday market, featuring local Charlestown businesses; as well as a skating rink, live music and other entertainment planned throughout the season.

Earlier this year, chef Will Gilson and his Cambridge hospitality group opened two new spots on First Street: all-day café and rotisserie Amba, and a next-door farmers market and events space, First Street Market. The latter is inaugurating its first holiday season with a series of maker markets December 14–15 and 20–21. The in-house bar will offer libations to fuel the festivities. All events will run 11am–3pm except for a nighttime edition on Friday, Dec. 20, which runs 5–9pm.

A massive music venue becomes a winter wonderland on Saturday, Dec. 21, when more than 130 unconventional vendors take over Roadrunner for the Holiday Bazaar. The 50,000-square foot concert hall will be filled with alternative kitsch curated by the Brighton Bazaar, proprietors of nearby Brighton Emporium indoor market. “We may not be your Grandma’s holiday market,” the organizers say, “but we do have all her sweaters!” Roadrunner’s bars will be open all day, along with a pop-up food court on the mezzanine level. Live DJs will be spinning to set the vibe. Tickets are $10 in advance, $15 at the door and $20 for first-dibs access at 11am. Otherwise, the event runs from noon–7pm.

This holiday season will look unlike any other, but still, after all, it’s that time of the year when we stay in with the family — or book in at one of the best restaurants in Boston for a feast prepared by someone else—more on that below. Looking for things to do in Boston over the holidays, as well as places to eat and play? We’ve got you covered.