Boston’s Best Outdoor Winter Activities

Boston transforms into a magical wonderland in the winter, and at The Envoy Hotel, Autograph Collection, we’re soaking up the charm of the city’s snow-covered streets. While staying warm is undoubtedly a priority, the winter season in Boston presents plenty of outdoor activities to make your stay unforgettable. For those who love being outdoors, we’ve curated a list of activities to ignite your adventurous spirit and see Boston from a new perspective.

Go for Drinks in an Igloo

Immerse yourself in Boston’s best skyline views, without sacrificing warmth at our modern rooftop bar, Lookout Rooftop. Our signature igloos are back for another year, providing a one-of-a-kind experience for our guests. Sip on your favorite cocktails while basking in the breathtaking views of the Boston skyline. The combination of a cozy atmosphere and the allure of the city lights create an experience that you’ll reminisce on long after you leave. Don’t miss the chance to elevate your winter evenings with us.

Sled Down Snowy Hills

Embrace the thick layers of snow that blanket Boston by grabbing your family or friends and heading to some of the city’s popular sledding spots. Arnold Arboretum at Harvard University, Danehy Park in Cambridge, Flagstaff Hill in Boston Common, and the Sugar Bowl at Jamaica Pond offer gravity-defying slopes that promise pure, unadulterated fun. Embrace the joy of speeding down snow-covered hills, creating cherished winter memories against the backdrop of the city’s snowy charm.

Learn History on the Freedom Trail

For those who appreciate a blend of outdoor activity and historical enrichment, the Freedom Trail is a must-visit. This 2.5-mile walking path connects 16 sites of historical importance in Boston. Whether you’re a history buff or just enjoy picking up fun facts, the trail takes you from the Boston Common downtown to the Bunker Hill Monument in Charlestown, including a visit to Boston National Historical Park. Near the trail’s beginning, explore the Boston African American National Historic Site, delving into the abolitionists of Beacon Hill and the significant contributions of people of color to Boston’s history.

Ski at Blue Hills

Escape the city without venturing too far by skiing at Blue Hills, approximately a 14-mile drive away. If you don’t have a car, Wachusett Mountain is accessible by the Commuter Rail in approximately two hours (with a free shuttle from the Fitchburg station during ski season). While Blue Hills provides a convenient slope experience, adventurers seeking bigger mountains and breathtaking views can explore popular skiing destinations like Bretton Woods in New Hampshire for a scenic day trip.

Hop on an Old Town Trolley Tour

If you prefer to take in the sights without braving the cold on foot, Old Town Trolley offers guided tours daily during the winter months. Marvel at the significance of Boston’s iconic sites from the warmth and comfort of an enclosed trolley. Enjoy the best of the city as a guide narrates your journey, letting you in on all of Boston’s most interesting and legendary stories. It’s the perfect way to explore the city without having to face the winter chill. After all, staying warm is key during a Boston winter.

Boston: An Award-Winning Experience

Our Seaport hotel has been nominated for Travel + Leisure’s 2024 World’s Best Awards, and we’re delighted to share this honor with you. When you share your favorite travel moments with Travel + Leisure, you will be entered to win a $15,000 cash prize or a Viking Expedition Voyage for two people.

So whether you’re hoping for an international vacation or choose to settle into Boston, we invite you to experience the city’s unique winter charm with our Weekend Getaway on the Harbor Package. Save on your weekend stay as you savor the welcoming warmth of our heated rooftop bar or set out to discover the best of the Seaport District. After exploring the beyond-ordinary activities and attractions that make winter in Boston so special, retreat to the warm, comfortable accommodations at The Envoy for a taste of true relaxation.