We all know the drill during the holidays in Boston: The skating line at the Frog Pond, the rush to grab tickets to the Holiday Pops at Symphony Hall, and the mad dash for front row seats to the Nutcracker at the Opera House. Don’t get us wrong, we love the classics. They are classic for a reason. But sometimes, you want the holiday magic without the tourist crush. You want the deep cuts. The B-sides.
If you are looking to trade the chaotic crowds for something a little more curated and cool, we’ve rounded up our favorite Boston unusual holiday activities. From gothic castles to indie markets, here is how to do the holidays in the city like a true insider with your kiddos.
Boston’s Offbeat Holiday Markets & Art Fairs
Listen, I love the idea of Snowport, but do I love waiting in a 45-minute line just to get into a shop to buy a candle? Not so much. For underrated holiday events in Boston, you have to look where the locals shop.
Take to the SoWa Winter Festival for an underrated Boston Christmas experience! Photo courtesy of SoWa Boston, Facebook
1. The SoWa Winter Festival
Located in the Power Station in the South End, this is the sophisticated older sister to the outdoor markets. It’s indoors (crucial for New England weather), features incredible local makers, and usually has a killer bar setup. It feels more like a festive art gallery opening than a crowded fair but you can still bring the kids.
2. Ghosts of Holidays Past at Salem Haunted Neighborhood
Spooky season is a lifestyle, not just a month. If you want Nightmare Before Christmas energy, this is it. Enjoy Victorian ghost stories, a kid-friendly “Glow Walk” (complete with magic glasses!), and a Winter Spirit Market for unique gifts and hot cocoa.
3. The Harvard Square Holiday Fair
If you want something with a bit more grit and history, head across the river. This fair has been running for decades and features eclectic, funky, and truly unique gifts. It’s less “mass-produced ornament” and more “hand-forged jewelry by a woman who lives in a yurt.” Very Cambridge, very cool.
Unexpected Outdoor Adventures
We are hardy New Englanders, so a little cold won’t stop us—but let’s make it worth the frostbite.
Take to the ice for a different spin on holiday fun! Photo by Michael J. Maloney, courtesy of Kendall Square
4. Skate @ Canal District Kendall
Swap the tourist traps for this chic rink in Kendall Square. It’s a local favorite for its pristine ice and top-tier après-skate scene—you are steps away from some of Cambridge’s best dining and cocktails. Pro Tip: Don’t miss the free Holiday on Ice Show on December 13th!
5. Hammond Castle Museum: Deck the Halls
Head up north to Gloucester. Hammond Castle is a medieval-style castle built by an eccentric inventor. Seeing it dressed up for “Deck the Halls” by candlelight is breathtaking. It’s moody, romantic, and totally unique.
6. “Ghosts of Christmas Past”: A Haunted Holiday Stroll
This Witch City Walking tour of Salem is straight out of a Dickens novel (literally). You’ll explore historic streets by lantern light, listening to Victorian ghost stories and true tales of the city’s darker history. It’s atmospheric, eerie, and the perfect way to get your “A Christmas Carol” fix without the cheesy musical numbers. Bundle up—the chills aren’t just from the winter air!
Unusual Performances and Events in Boston this Christmas
We love the Boston Ballet, but the city’s theater scene has so much to offer. If you want alternative holiday things to do in Boston, check the marquees at the smaller venues.
Unusual Performances and Events in Boston this Christmas
We love the Boston Ballet, but the city’s theater scene has so much to offer. If you want alternative holiday things to do in Boston, check the marquees at the smaller venues.
Try a fresh take on holiday clasics in Boston this Christmas. Urban Nutcracker photo by Peter Paradise
7. Anthony Williams’ Urban Nutcracker
This is hands down one of the best unique Christmas activities in Boston. It takes the classic Tchaikovsky score and fuses it with Duke Ellington, swing, hip hop, and tap. It’s vibrant, diverse, and captures the actual energy of the city. It feels like Boston, not just a fairy tale.
8. The Midwinter Revels
Held at the historic Sanders Theatre in Cambridge, this is a midwinter celebration that feels steeped in history. Every year focuses on a different culture or era (think Medieval, Nordic, Irish). It’s immersive, musical, and feels a little bit old-world magic—perfect for those of us who obsess over history.
9. Improv Asylum’s Holiday Show
If you’d rather laugh until you cry than sit through another earnest Christmas Carol, head to the North End. The Improv Asylum’s holiday show, Sleight it Again, is famously hilarious, irreverent, and always a sell-out for a reason. Obviously, this is one for older kids!
10. Winter Solstice at Mount Auburn Cemetery
A cemetery might not scream “holiday cheer,” but stay with us. Mount Auburn Cemetery is one of the world’s most beautiful garden cemeteries, and their annual Winter Solstice celebration is breathtakingly unique. Think thousands of luminaries lighting the winding paths, ethereal music, and a gorgeous, contemplative light projection show. It’s moody, magical, and utterly unforgettable.
Hidden Holiday Dining & Treats in Boston
11. L.A. Burdick’s Hot Chocolate
Forget Dunkin’ for a second. If you want the real deal, go to L.A. Burdick on Clarendon Street or in Harvard Square. Their “drinking chocolate” is basically melted ganache. It’s rich, decadent, and barely qualifies as a beverage. Grab one and walk down Commonwealth Avenue to see the lights.
12. Christmas Tea with Santa and Hannukah Celebration at the Inn at Hasting Park’s Town Meeting Bistro
The Inn at Hastings Park in Lexington is the place to be this December! There is Tea with Santa (December 13-14 & 20-21) where the kids get cocoa and crafts; you get cocktails and savory bites all while enjoying a moment with Santa. Then there is there Hanukkah Celebration (December 17-20) which is a special meal to honor the season.
Cozy Cultural Escapes
Get off the beaten path for holiday fun near Boston in 2025. Christmas by Candlelight photo courtesy of Old Sturbridge Village
13. Isabella Stewart Gardner Museum
Even in winter The Gardner’s courtyard is an oasis. While they don’t do “in your face” Christmas decor, the holiday time brings a quiet, lush green escape from the grey city. It’s a cozy cultural escape where you can pretend you’re an heiress living in her Venetian palace.
14. Old Sturbridge Village: Christmas by Candlelight
Okay, this is a bit of a drive, but for family travelers, it’s a must. It’s 1830s New England history come to life. Walking through the village at night with bonfires, carolers, and sleigh rides is pure nostalgia. It’s educational but magical, and the kids absolutely love it.
15. The Mapparium
This is an indoor “hidden gem” for a blustery day. It’s a three-story, inside-out, stained-glass globe from 1935 that you walk through. It’s not “holiday-themed,” but it’s a stunning, colorful, and otherworldly escape.
Tell us: What’s your favorite “under-the-radar” Boston holiday spot? Share it with a friend and start making plans!
