From Halloween and Oktoberfest celebrations to food tours, sporting events, and seasonal cultural festivals, fall is one of the most enchanting times to experience Boston at its best.
Visit Cambridge
Known globally for its academic excellence, Cambridge’s year-round beauty and unique annual events make it a must-see during your visit to Boston. Home to popular restaurants, museums, attractions, performing arts venues, and so much more, it is easy to dedicate a full day or even an entire weekend to exploring this iconic city. Cambridge offers young visitors valuable cultural enrichment and a unique glimpse into one of the world’s most prestigious academic environments.
Explore a Boston Museum
Boston’s museum scene is as diverse as its history. History enthusiasts can step into the nation’s past at the John F. Kennedy Presidential Library & Museum, the USS Constitution Museum, and the Boston Tea Party Ships & Museum, while art lovers can admire world-class collections at the Museum of Fine Arts, the Isabella Stewart Gardner Museum, the Institute of Contemporary Art or the Harvard Art Museum, which is now free to the public.
Attend a Show or Concert
Boston has an impressive roster of performance venues, offering everything from major concerts and Broadway productions to classical music and live entertainment. From TD Garden to the House of Blues, Symphony Hall to the Boch Center, and MGM Music Hall to Citizens Bank Opera House, there is a show on the calendar for every age and interest.
Halloween & Haunted Adventures
Fall is Boston’s spookiest season, with Halloween celebrations and haunted experiences across the city. Explore Boston’s past on a Ghosts and Gravestones Tour, a Haunted Boston Ghost Tour, or the Dark Side of Boston Tour, then head to nearby Salem for the iconic Haunted Happenings festival, the Salem Witch Museum, and themed walking tours. Families can also enjoy the 32nd annual PruBoo event at Prudential Center on October 25, featuring trick-or-treating, face painting, crafts, magic shows, and live entertainment. Whether you’re seeking spooky thrills or family-friendly fun, Boston offers a memorable Halloween experience.
The Iconic Head of the Charles Regatta
Whether you’re a first-timer or a seasoned veteran, there’s fun for everyone in the Head of the Charles Regatta. Held annually in October, this regatta attracts more than 11,000 athletes, making it the world’s largest 3-day regatta.
Neighbourhood Food Tours
One of the best ways to explore Boston’s 23 neighbourhoods is through their food options! Mix the fun of exploring the city on foot with some of the best flavours the city has to offer. Take a North End Pizza Tour, taste delicacies from one of the largest Chinatowns in the country with either Boston Chinatown Tours or Chinatown’s Culture and Cuisine Tour, explore innovative eats on the Davis Square Food Tour, or satisfy that sweet tooth during the Harvard Square Chocolate Tour. The flavours are as diverse as the city’s neigbourhoods.
The Great Elephant Migration
This summer, Boston’s Back Bay will become the newest city to join The Great Elephant Migration – a global public art movement using creativity to inspire human-wildlife coexistence around the world. From August 8 through September 13, one hundred life-size elephant sculptures will transform the historic Commonwealth Avenue Mall, spanning nearly a mile from Arlington Street to Fairfield Street, into an immersive outdoor exhibition that invites residents and visitors alike to experience the power of art as a catalyst for conservation, connection and conversation.
Embark on a Walking Tour
Fall is the perfect time to discover America’s Walking City on foot. Stroll through Boston’s iconic Beacon Hill neighbourhood, view some of Boston’s TV and movie locations through another lens, learn why Greater Boston is one of the most innovative areas in the country, or take a journey into history along the Freedom Trail. Make sure to visit the Boston Common Visitor Center to find them all.
Boston Sports Teams
Boston is a sports lover’s dream year-round, but fall is a particularly exciting time. Cheer on the New England Revolution and New England Patriots at Gillette Stadium or the Boston Bruins and Boston Celtics at TD Garden. Beyond professional teams, you may also attend one of the many collegiate sporting events and soak in the energy and passion of the student community.
Oktoberfest
Oktoberfest is an annual celebration of beer, bratwurst, live music and community spirit. Throughout the fall season, Boston and its surrounding neighbourhoods host popular events including Harvard Square Oktoberfest, Harpoon Oktoberfest and Dorchester Brewing Oktoberfest, offering visitors a festive way to experience autumn in New England.
