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Embracing the Winter Wonderland: 20 Things to Do in Boston During the Chilly

Embrace the winter in Boston with a myriad of activities during the chilly season. Glide gracefully across the Boston Common Frog Pond’s ice rink or explore the city’s rich history through indoor attractions like the Museum of Fine Arts. Warm up with a cup of clam chowder at Quincy Market or catch a thrilling game at the TD Garden. Embrace the festive spirit with holiday lights on Commonwealth Avenue, creating a magical ambiance. Boston in winter offers a perfect blend of outdoor adventures and cozy indoor experiences.

  1. Ice Skating on Frog Pond: Start your winter adventure by gliding across the ice at the Boston Common Frog Pond. Surrounded by the city skyline, this outdoor rink is a picturesque spot for both beginners and seasoned skaters.

  2. Boston Winter Village: Immerse yourself in the holiday spirit at the Boston Winter Village, where you can explore festive markets, enjoy seasonal treats, and even shop for unique gifts from local artisans.

  3. Skiing at Blue Hills: For winter sports enthusiasts, a day trip to Blue Hills Ski Area offers skiing and snowboarding opportunities, providing a taste of the slopes just a short drive from the city.

  4. Winter Lights at the Boston Common: Marvel at the breathtaking Winter Lights at the Boston Common, where the trees are adorned with thousands of twinkling lights, creating a magical ambiance.

  5. Boston Tea Party Ships and Museum: Dive into history at the Boston Tea Party Ships and Museum, where interactive exhibits and reenactments bring to life one of the most pivotal moments in American history.

  6. Visit the New England Aquarium: Escape the cold by exploring the wonders of the sea at the New England Aquarium. From mesmerizing marine life to captivating exhibits, it’s a perfect indoor activity for families.

  7. Cozy up at a Historic Pub: Warm up with a hearty meal and a pint at one of Boston’s historic pubs. Enjoy the cozy ambiance and rich history as you indulge in local fare.

  8. Boston Symphony Orchestra Concerts: Experience the enchanting melodies of the Boston Symphony Orchestra during their winter season. The renowned orchestra often performs classical masterpieces and holiday favorites.

  9. Snowshoeing in Arnold Arboretum: Discover the beauty of winter landscapes by snowshoeing through the Arnold Arboretum. The serene trails offer a peaceful retreat amidst nature’s winter beauty.

  10. Winter Whale Watching: Brave the chilly winds for a unique winter whale-watching experience. Witness majestic creatures like humpback and minke whales as they migrate along the Massachusetts coastline.

  11. Indulge in Hot Chocolate: Warm your soul with a cup of rich hot chocolate from one of Boston’s top-notch chocolatiers. Bonus points if you find a cozy café with a fireplace.

  12. Boston Public Library: Escape the winter chill by exploring the Boston Public Library. Admire the architecture, peruse rare books, or simply find a quiet corner to read and relax.

  13. Boston Celtics Game: Cheer for the home team at a Boston Celtics game. The electric atmosphere at the TD Garden is sure to keep you warm, even on the coldest winter nights.

  14. Historic Freedom Trail Tour: Take a stroll along the iconic Freedom Trail, guided by costumed interpreters. Discover Boston’s rich history as you visit historic sites like Paul Revere’s House and the Old North Church.

  15. Boston Common Tree Lighting: Join the festive crowd for the annual Boston Common Tree Lighting ceremony. Witness the grand illumination of a towering Christmas tree, marking the official start of the holiday season.

  16. Boston Winter Film Festival: Embrace the winter vibes at the Boston Winter Film Festival. Cozy up in a theater and enjoy a selection of seasonal classics and contemporary films.

  17. Explore the Museum of Fine Arts: Delve into the world of art at the Museum of Fine Arts. Wander through the galleries and appreciate masterpieces from various cultures and time periods.

  18. Winter Hike in Middlesex Fells Reservation: Lace up your boots and embark on a winter hike in the Middlesex Fells Reservation. The snow-covered trails offer a serene and invigorating outdoor experience.

  19. Boston Harbor Islands Ferry Tour: Enjoy a scenic ferry tour around the Boston Harbor Islands. While it may be chilly, the views of the city skyline against the backdrop of the Atlantic Ocean are truly mesmerizing.

  20. Boston Comedy Shows: Wrap up your winter escapades with laughter at one of Boston’s renowned comedy clubs. A good laugh is the perfect way to warm up during the colder months.


Boston in winter is a captivating blend of history, culture, and seasonal festivities. Whether you’re gliding on ice, sipping hot cocoa, or immersing yourself in the city’s rich heritage, there’s no shortage of ways to embrace the magic of the season. So bundle up, explore the winter wonderland of Boston, and create cherished memories that will warm your heart for years to come.