Celebrate the Most Wonderful Time of the Year at Boston’s Best Holiday Events

An events guide to the best Boston Christmas market and more seasonal fun.

Boston Christmas Market
Snowport | Lindsay Ahern, photo courtesy of Snowport
Snowport | Lindsay Ahern, photo courtesy of Snowport

The lights are twinkling and there’s so much holiday spirit in the air that Boston’s drivers are lightly tapping a beep-beep instead of laying on the horn, right? Maybe that’s just an egg-nog-fueled daydream, but it’s hard to deny that the city is brimming with good cheer this season—festive vibes and champagne cocktails alike.

From the annual winter wonderlands and holiday markets that locals look forward to all year to new holiday events joining the mix (including cocktails served in festive-clad dinosaurs, holiday music trivia, an orchestral Kwanzaa performance, and a holiday market curling lesson), it’s a winter wonderland out there. Plus there are plenty of ways to give back to the community. ‘Tis the season for Boston's best holiday events.

Boston Christmas Market
Miracle: A Christmas Cocktail Pop-Up Bar | Photo credit: Melissa Hom

Holiday Drinking in Boston

November 24–December 24, 5 pm
Cambridge, Free entry
The globe-trotting, Christmas-themed pop-up cocktail bar is delivering sippable festive cheer in Cambridge this year at Hotel Marlowe with over-the-top libations like the minty, tequila-based Christmas Crickets and the almond-milk-based Jingle Balls Nog (cocktails start at $10). Drinks are served in spectacular cocktail glasses, some of which you can buy. One and done shopping? We'll drink to that.

December 7, 8 pm
Everett, Free entry
Remember when your partner joked that your holiday music knowledge is cute but useless? Well, the taps at Bone Up Brewing Company will soon flow with the seasonal favorite Biere de Krampus (a hearty holiday ale with ginger, figs, and honey)—and that can mean just one thing. It's time for the holiday edition of Audio Triviality’s Music Trivia. So brush up on themes like Belsnickel, Santa, and—yes—their sadistically scampish counterpart, Krampus, who terrifies children who have misbehaved (ah, Christmas memories). Holiday terror aside, now's your time to shine as bright as Rudolph's nose while going all out on the Christmas carols and Hanukkah songs trivia.

December 7 and 14, 4 pm
Downtown, Free entry
Walk right into the ultra-cozy library at The Dagny Boston to find glimmering trees, live tunes from Berklee College musicians, and a champagne attendant ready to pour you a glass of bubbles. The completely free experience makes the perfect amuse-bouche for a holiday date night. Better yet, pop in just because and soak up all the holiday magic. The staff won't let you move in and stay forever but they will give you that glass of bubbles and a luxurious moment of holiday tranquility.

December 13, 7 pm
Cambridge, $89
Cambridge's event-savvy Bonde Fine Wine Shop is ushering in the Festival of Lights with an intimate Jewish foods and kosher wine pairing event limited to just eight people. Owner and sommelier Bertil Jean-Chronberg will empower you with enough next-level wine know-how to make your friends and family linger long into the night. The class includes a flight of four wines, light bites, and oodles of sommelier secrets.

December 24, 9 pm
Downtown, Starting at $50
The laudedgrandaddy” of Jewish holiday parties marks its 37th year of Christmas Eve revelry with live DJs spinning hip hop, house, and more at the Royale. The lively, packed dance floor barely leaves room for a sprinkle of Kosher salt between revelers, and maybe meet your soulmate. No matter what, you'll definitely ditch all the Santa-saturated TV viewing and maybe, just maybe, throw back some shots. Tickets sell out fast, so if you're looking to switch it up this year, set the dreidel aside and put your party pants on.

Winter Sports Events in Boston

Seaport District, Free
Don't tell pickleball, but a new sports darling is in town—and she's a cold-weather legend. Once just a niche sport in the Winter Olympics, curling’s popularity is booming. Get in on the action with a free, 30-minute lesson at the Seaport District with the North End Curling Club. Plus, it’s the perfect stop while you’re visiting the annual Snowport wonderland, where you can also look out for the famed Betty the Yeti, shop the Holiday Market, buy a fluffy Christmas tree, warm up in the Envoy’s rooftop igloos, or check out the Light Up Seaport and Menorah Lighting events along the way. Reservations are required for curling lessons, which are held Saturdays from 2 pm to 4 pm.

Downtown, Prices vary
The holidays aren't complete without a failed double-Lutz jump at Boston’s famed outdoor ice skating rink. Frog Pond is one of Boston's most cherished (and wholesome) winter traditions. Set along the walking paths of Boston Common, the small rink offers skate rentals, and you can buy a hot chocolate to help keep your hands warm. The trees of the Common are festooned with holiday lights–giving irresistible Hallmark Christmas movie vibes–and the nearly 400-year-old park is aglow with holiday magic.

December 27, 7:30 pm
West End, Starting at $37.50
Nothing screams the holidays quite like a Hulk Hogan-style Atomic Leg Drop, so save the date for the WWE's Holiday Tour Live at TD Garden. Beloved basher Rhea Ripley is featured in many promotions, but keep your fingers crossed since the rotating line-up is full of surprises. Whether you're a SmackDown, NXT, RAW, or Survivor Series fan, TD Garden is bringing the late-holiday-season noise that makes the chaos of family bickering look downright cordial.

Boston Christmas Market
Boston Symphony Orchestra's annual Holiday Pops | Photo credit: Hilary Scott, photo courtesy of Boston Symphony Orchestra

Holiday Arts and Culture Events in Boston

Holiday Tree Lighting Celebrations in Boston

November 25 and 30
Citywide, Free
To thank Boston for sending aid after a devastating explosion in Halifax in December 1917, Nova Scotia sends a huge Christmas tree each year. Kick off the season with the 82nd year with the 82nd Boston Common Tree Lighting when, starting at 6 pm, the official Christmas tree and lights throughout Boston Common and the Public Garden light up in sequence. At 8 pm head over to Commonwealth Avenue, when the trees there will be set aglow and you can score cookies and hot chocolate.

Theater District, Prices vary
The Boch Center is breathing new life into the holiday classics this year. Rudolph the Red-Nosed Reindeer: The Musical (November 24–26) kicks off the festive season with Rudolph (and Bumble the Abominable Snow Monster!) coming to life in costumes that match the original 1964 cartoon. (MJ O'Connor's andLegal Sea Foods are both offering pre-show dining packages.) Next, the Boch Center unleashes Elf in Concert (December 22–23) with the orchestra performing the movie score in real time as the film shows on the big screen.

November 25–December 25
Downtown, Free
Four frosty weeks of festivities, twinkling trees, and larger-than-life snowflakes at Snowflake Crossing kicks off at noon on November 25, when 100 tuba players rock the holiday classics on the Downtown Crossing steps. On November 30, the play ship at Martin’s Park, decked out in holiday lights, gets illuminated following a celebration with hot chocolate, a real fire truck, and a visit from The Grinch. Throughout the season, Summer Street Plaza hosts musicians, food vendors, a holiday market, and carolers. Plus, check in with Santa on the weekends to see about getting your name off the naughty list.

December 1–24
Fenway–Kenmore, Prices vary
The Boston Pops' annual Holiday Pops show is nothing short of spectacular. The theater’s acoustics are primo and the room is filled with both the vibrations of booming orchestra music. But it’s the near-tangible feeling of hope filling the room that creates a few moments when there isn't a dry eye in the house (darn you, nostalgia!). The musicians offer a reprieve by mixing it up between big classics and silly riffs on holiday movie scores. Yes, there's also a brief yet zippy sing-along, and if you ho-ho-hope hard enough, you might get a special visitor.

December 2, 3 pm
Forest Hills, Free entry
Black artistry's elegant and deeply felt power is front and center this festive season, as Castle of our Skins presents Brian Raphael Nabors's Kwanzaa Suite as part of the Celebrity Series of Boston. It’s performed in seven parts (each exploring the Nguzo Saba, the seven principles of Kwanzaa) along with African and pan-African selections such as Monthati Masebe's Nomadic Nirvana for string quartet, a gorgeous Ugandan piece, and more. All are invited to join the season's beauty and embrace kuumba (creativity) at this free event at Bethel A.M.E. Church.

December 16, 8 pm
Back Bay, Starting at $34.50
Kriss Kringle probably won't deliver a stocking full of cinematic perversion, but you know who will? The one and only John Waters. The renowned counter-culture filmmaker is coming to Boston for A John Waters Christmas presented by The Bowery Boston. For one day only, catch an in-person glimpse into the inner workings of Waters's wicked brand of genius. He's got a holiday goodie bag stuffed full of his obscenely dark comedy—and for an upcharge, you can join a smaller group of fans to hang out with him for a “group therapy” sesh or post-show Q&A.

December 27–31
South End, Starting at $25
‘Tis the season to order a few cocktails and argue whether or not the fact that Die Hard’s bomb-diffusing storyline taking place at a Christmas party is enough to land it on the Christmas movie list. Yippee Ki Yay, a one-man parody paying tribute to the 1988 classic action romp starring Bruce Willis, lands at the Huntington Theater just in time for the great holiday debate. Besides, some of the best Christmas movies aren’t about Christmas.

Christmas Market Boston
Studio by Garden Streets | Photo courtesy of Studio by Garden Streets

Holiday Shopping in Boston

Cambridge, Starting at $55
This bustling maker space helps you deck the halls with holiday workshops teaching expert-level holiday skills. Make your own evergreen winter wreath (December 2 and 15, $110) using a fresh evergreen starter-wreath before adding on extras like other greenery, pinecones, and festive ribbon. At the Art of Gift Wrapping class (November 25 and December 9, $55), learn advanced wrapping skills that will make for a more polished-looking package and the courage to ditch the lame gift bags.

Throughout December
Citywide, Prices vary
Skip the commercial stores on Black Friday to shop at SoWa Artists Guild for one-of-a-kind work from over 80 artists. Visit Dorchester’s outdoor Holiday Market at The Lot for clothing, jewelry, and Boston-themed gifts together with cozy cocktails and photos with Santa (December 2–3). Small Mart’s holiday market (December 2, 16, 23) brings together over 20 vendors with vintage and handcrafted gifts. And Beacon Hill's The Hidden Art Gallery has transformed into a winter wonderland for the Holiday Art Show, where you can stock up on giftable watercolors, digital prints, and framed photography, starting at just $25 (weekends, December 2–16).

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Melanie Carden is a private chef turned travel writer. She’s equal parts adrenaline-seeker and Golden Girls vibes. You can find her trying new things, thrifting for treasures, grinding it out on a trail, or lounging on a picnic blanket—Aperol spritz in hand. She's fickle about social, but the sporadic nuggets are worth the wait—cricket tacos, anyone?