Your Guide to Fall in Boston

Halloween Decorations in Beacon Hill

The kids may have gone back to school, but boating season is not over yet! With discounts on dockage at Boston Yacht Haven and pumpkin back at Dunkin’, now is the time to bring the boat to New England enjoy what is arguably the most beautiful time of year in this region.

Fall Foliage along the Charles River Esplanade

Many leaf-peepers flock to this region to scope out the best fall foliage. And while the Berkshires are known for their incredible views, you do not need to travel out west to stumble upon the stunning colors of autumn in New England. In Boston, stroll through the Boston Common and Public Garden or along the Charles River Esplanade. Wander through the streets of Beacon Hill and snap a photo on Acorn Street. Take a short ferry ride to one of the Boston Harbor Islands and spend the day on the walking trails and taking in the nature views with the Boston Skyline as your backdrop.

Vintage Book Shop

Fall is a great time to curl up with a good book – the Boston Book Festival is Saturday, October 14th in Copley Place with presentations from a number of distinguished authors. Looking to shop for some new reads? A local favorite is the Brattle Book Shop on West Street in Boston. 

A New England Fall tradition is the Head of the Charles Regatta. Rowers from across the country gather to Boston for this exciting weekend. Another annual favorite is the Topsfield Fair, just north of Boston. Complete with parades, contests, food, concerts, and more, this fair is fun for the entire family. 

'Tis the season for Oktoberfest! Enjoy a brew in Harvard Square or Hood Park this season! Or if beer isn't for you, visit Ciderfest at Time Out Market.


Embrace the spooky spirit of fall by taking a Ghosts and Gravestones Tour in Boston. If you really enjoy Halloween, a day trip to Salem is a must-do. It is just a short ride from Boston on the commuter rail or ferry. Check out the Salem Witch Museum or the Peabody Essex Museum while you are there. Shop and dine at Pickering Wharf and spend the evening playing games at the Salem Willows. The beloved Halloween film "Hocus Pocus" was set in Salem, test your knowledge of the film at a Hocus Pocus Trivia Night at the Sam Adams Downtown Tap Room on October 17th.

Back in Boston, Fall-O-Ween will be fun for the entire family on October 20th.

Autumn in Boston

This fall, see a Red Sox game at the historic Fenway Park. Attend one of the many farmer’s markets in Boston. Find something special at the SoWa vintage market or the Fenway Flea. See the Boston Lights at the Franklin Park Zoo or visit the Quincy Quarries. Take a ride to Wilson Farm in Lexington to pick out some pumpkins and enjoy delicious apple cider donuts. 

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