The weather is a gamble, but Boston during the holidays is worth every frosty breath. We rounded up something for every type of winter explorer, whether it's wandering through twinkling light displays or sipping festive cocktails at local holiday markets. Consider this your spirited roadmap to making the most of the season.
Photo Credit: Boston Magazine
Shop the Merriest Holiday Markets Around Boston
If holiday shopping is an art, then Boston’s markets are the galleries. 'Tis the season to explore the best holiday markets near Boston.
Seaport transforms into Snowport, a winter playground filled with artisans, snacks, holiday games and gifts for everyone on your list. Don’t miss the Snowport Tree Market, where rows of evergreens infuse the air with pine-fresh energy.
Continue your hunt at the SoWa Winter Festival & Holiday Market, featuring over 125 local vendors, handmade art, indie gifts and seasonal bites that warm you from the inside out. Other festive favorites include the South Boston Christmas & Holiday Market, Boston Public Market’s Holiday Shopping Market, and the charming Andover Holiday Market.
Still stumped on gifting? Explore Boston’s best local shops or pick up something calming and creative from the Boston Cannabis Gift Guide.
Photo Credit: Loco Fenway
Sip and Savor at Boston’s Holiday-Themed Bars & Restaurants
Whether you’re on the naughty list or the nice one, you deserve a holiday drink in a cozy, over-decorated wonderland, and Boston definitely delivers. Pop into the Holly Jolly Bar at Harpoon Brewery for peak festive cheer, or sip tropical-holiday cocktails at Sippin’ Santa at Shore Leave. For a jolly twist on Mexican cuisine, check out Santa’s Cantina at Loco Fenway, and if you’re feeling bold, step into the Naughty List Lounge at The 88 Club. Don't miss Maccabee Bar, Boston's only Hanukkah pop-up.
Photo Credit: Boston Uncovered
Chase the Glow at Boston’s Best Holiday Light Displays
Grab a friend (or just your warmest pair of mittens) and let the city guide you from one magical display to the next. Start with Boston’s top tree lightings, then continue your own illuminated adventure. A few standout spectacles include the vibrant ZooLights at Stone Zoo and the city’s annual Menorah Lighting along the waterfront. Venture a bit farther for the enchanting Night Lights at the New England Botanic Garden, or take a whimsical walk through the Somerville Illuminations Tour, a beloved DIY tradition where every street shows off its holiday best.
Photo Credit: TD Garden
Cheer Like a Local: Holiday Season Sports in Boston
Catch the Pats at one of the best bars to watch football or cheer on the Celtics and Bruins at these basketball and hockey spots. Whether you’re inside the Garden, bundled up at Gillette or catching the game from a bar, Boston sports hits differently during the holidays.
Photo Credit: Killington
Find Your Winter Thrill: Skiing, Sledding & Ice Skating Near Boston
If winter is your playground, you’re in the right region because the best of New England’s slopes are just a scenic drive away. Explore the best skiing and snowboarding near Boston for trails ranging from beginner-friendly to utterly exhilarating.
Prefer your snow fun at ground level? Visit the best sledding spots or lace up at these ice skating rinks around Boston. Whichever adventure you choose, winter outside Boston is an absolute thrill.
Photo Credit: Time Out Boston
Step Into the Spotlight: Boston’s Must-See Holiday Performances
We had to include holiday theatre, dance and orchestral magic this time of year. There's nothing like seeing the Boston Pops at Symphony Hall as they blow your holiday-loving mind into a snowglobe of joy.
For more seasonal shows, check out ’TWAS THE NIGHT BEFORE… at the Boch Center Wang Theatre, The Nutcracker at the Boston Opera House, and Anthony Williams’ Urban Nutcracker at the Boch Center Shubert Theatre, each one offering its own flavor of festive enchantment.
Photo Credit: Encore
Countdown in Style: Ringing in the New Year in Boston
Still deciding how to spend New Year’s Eve? We got you. Explore our NYE event guide filled with concerts, parties, dinners and celebrations across the city. Whether you’re seeking a full night out, a classy pregame spot or a family-friendly countdown, Boston offers dozens of ways to welcome in the new year.
Updated December 2025
