A cobblestone street lined with brick buildings, autumn leaves, and decorated doorways in a quaint neighborhood setting.

Best Ways to Enjoy Fall in Boston

Published on September 23, 2025

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Autumn in Boston is a season of understated elegance. The city is transformed with golden leaves along historic streets, colorful parks, and crisp, refreshing air perfect for a leisurely stroll. From the serene waterfront to quiet garden paths, Boston in the fall is as captivating as it is welcoming. 

The season also brings a sense of celebration. Festivals, regattas, and neighborhood traditions fill the city with energy, artisanal breweries, adn local markets offer the rich flavors of fall. Whether you are drawn to the history, the scenic beauty, or the seasonal experiences, Boston offers countless ways to savor the season. 

Ready to make the most of the season? Here are some of the best things to do in Boston this fall. 

Boston Harbor Hotel

Fall Foliage Cruise

Step outside Boston Harbor and embrace the season on Charles River Boat Company's Fall Foliage Cruise, where crisp air and vibrant waterfront trees create a breathtaking backdrop. The cruise offeres a truly unique perspective on Boston Harbor at its most colorful.

A rowing team in a red boat is moving through the water, with each member synchronized in their strokes.

Head of the Charles Regatta

October brings the Head of the Charles Regatta, a Boston tradition set against the crisp autumn skies of the Charles River. Guests can watch rowers glise past golden foliage, soak in the lively atmosphere, and enjoy one of the city's most iconic seasonal events.

Boston Harbor Hotel

Harpoon Brewery's Oktoberfest

Celebrate the season at Harpoon Brewery's Oktoberfest in the Seaport District, where fall comes alive with craft beer, live music, and festive flavors. Guests can sample Harpoon's seasonal brews, enjoy Ocktoberfest fare, and soak in the vibrant autumn energy along the harbor. Whether you're a beer lover or simply looking for a fall seasonal outing, Oktoberfest at Harpoon is a perfect autumn experience in the city.

The image shows a statue on a pedestal in a park, surrounded by autumn trees and city buildings in the background.

Explore Boston's Seasonal Beauty

Beyond the harbor, the city transforms into a canvas of golden leaves and vibrant colors. Discover the seasonal beauty of the Rose Kennedy Greenway and Christopher Columbus Park, or follow the Freedom Trail for a historic journey. From charming neighborhoods to iconic architecture, fall in Boston invites guests to explore, unwind, and savor every moment of the season.

    This fall, let Boston Harbor Hotel be your gateway to the season. With sweeping views and unparalleled access to the city's autumn traditions, every stay is designed to capture the beauty and spirit of Boston in its most picturesque season. Book your fall escape today. 

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