The Ultimate Guide to Fall in Boston, MA

A comprehensive guide for everything to do after you’ve ordered a PSL

Whether you are a frequent visitor, traveling from long distances, or a local who is looking to roam around the city, we gathered things to do in Boston, fall edition… Create a picture perfect moment at these must-see stops!

The Head of the Charles Regatta

One of Boston’s most anticipated sporting events, the Head of the Charles is the world’s biggest 3-day rowing race. The 3-mile race begins at Boston University’s DeWolfe Boathouse and finishes at the 7th bridge of the race, the Eliot Bridge between Cambridge and Allston. Boston hosts over 11,000 skilled athletes who take part in the competitive race during the peak of October foliage. Many top rowers travel across the world to compete in the event. Crowds of up to 300,000 cheer on the rowers as the athletes kick it in gear for the final stretch. If you’re looking for things to do in Boston during the fall season, the Head of the Charles Regatta this October 21st – 23rd is one event you won’t want to miss.

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Go on a Whale Watch

Set sail on a whale watch for a memorable experience with the New England Aquarium. September and October are peak months for catching sight of the many humpback, finback, pilot and minke whales when conditions are ideal for sightings. Departing from the aquarium to an active area called Stellwagen Bank National Marine Sanctuary you’ll discover a variety of different whale species. Set your expectations high and learn about these fascinating animals while sailing across beautiful New England waters.

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Take in Crisp Fall Air at World’s End

Spend a day hiking at World’s End located in Hingham, Massachusetts located 18 miles from Boston Harbor Hotel. This 244-acre peninsula overlooks Hingham Bay, formed by two drumlins with coastal impressions formed by glaciers many years ago.  Plan a day hike to see some of New England’s best fall foliage or go on a Full Moon Hike.  Take an afternoon kayak tour, grab your binoculars for a bird walk or learn from Karen Wong at a portrait photography fall-focused workshop.  The Trustee of Reservations puts on a variety of seasonal programming you can register for before your stay at the hotel.

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Best Places to Watch the Patriots

With fall, comes football season…  Kick off your Sunday and watch Boston’s most beloved team, the Patriots. Whether you like to watch the game in the comfort of your own home or out with friends in Boston’s most iconic sports bars and restaurants, visit these hotspots for good people, a good time, and good brews.


1. Tony C’s Sports Bar & Grill | Seaport District


2. Cask n Flagon | Next to Fenway Park


3.  Banners Kitchen & Tap | West End Boston


4. CBS Sporting Club | Foxborough

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Walk Along The Esplanade

The Esplanade is quite the view, located between the Museum of Science and Boston University’s Bridge. Stretching along the Charles River for 3 miles offering shaded green space overlooking the water, find a perfect park to run, jog, or sightsee this fall season.

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Crowd clapping at theater performance

Attend a Musical

As weather cools, keep warm and watch a musical in one of Boston’s state-of-the-art theatres. This fall season is brining incredible performances to the stage:



The Tina Turner Musical | Citizens Bank Opera House

Sep 20 – Oct 2

Little Shop of Horrors | North Shore Music Theatre

Sep 20 – Oct 2




Drumfolk | Emerson Cutler Majestic Theatre Oct 5 – 16

Hairspray  | Citizens Bank Opera House – Oct 18 – 30

Kinky Boots | North Shore Music Theatre – Oct 25 – Nov 6




Six The Musical | Emerson Colonial Theatre – Nov 9 – Dec 31

“Twas the Night Before, Cirque Du Soleil | Wang Theatre

Nov 25 – Dec 11

Boston Ballet: The Nutcracker | Boston Opera House Nov 25 – 31


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Embrace the new season and read our latest guide on the Best Places to See the Fall Foliage. From local spots around the city to taking a short trip up north, find our favorite places to see the vibrant leaves. Link in bio 🍂

#BostonHarbor #FallinBoston

Happy First Day of Fall. What are you most excited about this season?!

#FirstDayofFall #Fall #BostonHarbor

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