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Things to do in Boston in the Fall

Your Guide to Seasonal Attractions

Boston is famous for its iconic fall foliage, and tens of thousands of people pour into the city every year to watch the leaves change in our gorgeous and historic city. With so much to do, we know it can be a bit daunting as to where to start, but The Inn at Longwood Medical is proud to be your hub for Boston fall activities. From spooky tours to sophisticated culture, here's a few of the best things to do in Boston in the fall.

Walk the Freedom Trail

The 2.5-mile red-lined journey through American History is not only a great way to learn more about American Revolution, it's also one of the best ways to see the famous Boston foliage. From the Paul Revere House to Boston Common, the Freedom Trail is the most picturesque way to see historic Boston in the fall. 

Ghost and Gravestones Tour

As one of the oldest cities in America, Boston has more than its fair share of ghost stories, and the Ghost and Gravestones Tour is the best way to learn about the dark and spooky side of the city. Journey into ancient cemeteries and walk the same streets as the Boston Strangler with this chilling seasonal tour.

Boston Book Festival

The yearly literary event in Boston highlights the power of words and seeks to promote reading and ideas that match the spirit of Boston. This year's festival features talks and appearances by luminaries such as Tom Perrotta, Maureen Dowd, and Dennis Lehane. October 28. 

The Head of the Charles Regatta

The largest two-day regatta in the world, the 53rd Annual Head of the Charles Regatta will attract thousands of spectators to the banks of the Charles River. With participants ranging from 14 to 85 years old, this storied event is perfect for both seasoned rowing fans and travelers seeking a beautiful Boston autumn day. October 21 and 22.

The Faneuil Hall Marketplace Tree Lighting

One of the largest Christmas trees in Boston, this iconic tree decorates Faneuil Hall and is home to the Blink! holiday lights and music show. As fall gives way to winter, celebrate the changing of the seasons with live entertainment, culminating in the live broadcast of the tree lightning at 8pm. November 19.

For more information about the best things to do this fall in Boston, reach out to our helpful concierges who are ready and willing to give you expert local advice.