Things to Do in Boston: Winter Wonderland Edition ❄️🎥
Boston in winter? It's more than potholes and snowbanks. Whether you're a lifelong Bostonian or just visiting, there's a magical chill in the air (and no, we don't just mean the temps). Winter is the perfect time to bundle up, gather your crew, and embrace the festive vibes around the city. From iconic winter traditions to hidden gems, here's your go-to guide for making the most of a Boston winter.
1. Attend the Boston Common Tree Lighting Ceremony
Kick off the holiday season with the annual tree lighting at Boston Common. This beloved event features an ice skating show, live music, and a dazzling fireworks display. Typically held in the first week of December around 5 PM, it's a festive gathering that brings the community together.
2. Go on a Walking Tour
Experience Boston's rich history and festive charm by joining a walking tour. Explore cobblestone streets adorned with holiday lights and learn about the city's past from knowledgeable guides. Popular tours include the Freedom Trail, North End & Little Italy, and Cambridge & Harvard.
3. Take in Panoramic Views from the Skywalk Observatory
For breathtaking views of Boston's winter landscape, visit the Skywalk Observatory atop the Prudential Center. Enjoy 360-degree vistas of the city's historic sites and holiday lights, all accompanied by an informative audio tour.
4. Cozy Movie Night with Chick Flick & Chill
Who says winter fun has to mean frostbite? Stay warm and toasty indoors with Chick Flick & Chill’s winter movie packages. Whether you’re hosting a Super Bowl bash, a romantic date night, or a magical teepee slumber party for the kiddos, we bring the full cozy experience to you. Think plush seating, festive décor, and a giant screen for your favorite flicks—zero shoveling required. 🏠✨
5. Explore Snowport in the Seaport
Snowport is Boston’s ultimate winter playground. From curling lanes (yes, that sport with brooms!) to festive food trucks and pop-up shops, it’s a one-stop winter fun factory. Don’t miss the massive Christmas tree and enjoy a steaming cup of hot chocolate while you wander. Pro tip: Bring your camera—it’s Insta-gold. 📸
6. Hit the Slopes (Kind Of)
Who needs the mountains when you’ve got Blue Hills Reservation just outside the city? Perfect for a quick ski or snowboard run, it’s close enough to squeeze in a morning of fun before heading back to the city for dinner. Not into skiing? No worries—there’s also a great spot for sledding or just soaking in those snowy vibes.
7. Treat Yourself at Eataly Boston
Winter is prime carb-loading season, right? Warm up at Eataly Boston with a hearty bowl of pasta, a creamy risotto, or a slice of wood-fired pizza. If you’re feeling adventurous, try their seasonal offerings or grab some gourmet goodies to cook up your own feast at home. Bonus points if you pair it with a cozy rom-com from Chick Flick & Chill. 🍝🎥
8. Warm Up with a Brewery Tour
Boston’s craft beer scene is legendary, and winter is the perfect excuse to sip on some rich, toasty stouts or spiced ales. Harpoon Brewery’s Winter Warmer is a must-try, and Samuel Adams always delivers with seasonal brews. Grab your crew and make a day of it—it’s like a holiday party in a glass. 🍺🎄
9. Wander the Boston Public Market
For a dose of local flavor, the Boston Public Market is a winter favorite. From artisanal treats to handmade crafts, it’s a great place to shop for holiday gifts—or just snack your way through the stalls. Don’t miss the apple cider donuts. Trust us. 🍩✨
10. Take a Snowy Stroll Along the Charles
Bundle up and take in the serene beauty of the Charles River Esplanade. It’s quieter in the winter, with fresh snow blanketing the trails. The views of the city skyline against a frosty backdrop are unbeatable. Perfect for a romantic walk or just some much-needed fresh air.