Weather, Foliage, and Events Combine to Create an Idyllic Fall Getaway in Boston

September and October steal the show when it comes to the best months, in Boston. Magnificent weather, spectacular foliage, and a variety of engaging and festive events combine each fall to create the perfect time to live in, or visit, the city.

Bostonians spend all summer aching for the fall, and once it arrives there’s a palpable excitement in the air. Everyone loves to be outdoors, whether it’s for a picnic in the scenic Public Garden or for one of the many festivals. Though we encourage trips to Boston any time of year, yes even the winter months have certain advantages, autumn truly is the pinnacle time to visit.

Plan Your Fall Getaway in Boston – Here’s What to Do

For those of you considering a fall Boston getaway, enjoy this quick read on which events you can look forward to.

The Berklee Beantown Jazz Festival

September 29

Known as Boston’s largest block party, this is a free annual outdoor public concert featuring jazz, Latin, blues, funk, and groove performances. The performances take place across three different stages, and in between shows you can mill about the various food vendors.

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fall getaway in boston

Boston Book Festival

October 13

In this day of binge-watching and constant screen time, a festival celebrating one of life’s most precious gifts, reading, is a welcome reprieve. Taking place in the iconic Copley Square, the Boston Book Festival is a day of celebrating the power of words, a reading culture, and the beauty of Boston.

Head of The Charles Regatta

October 20-21

The world’s biggest two-day rowing event is quite the unique experience to have. Quite possibly one of the most quintessential east coast things one can do, the Regatta draws a crowd of 300,000+ who line both sides of the Charles River to catch sight of the races. Over the course of two days, there will be 55+ events, allowing you plenty of freedom to pick and choose which you’d like to observe.

RELATED: Everything You Need to Know About The Head of The Charles Regatta


September 28-29

One of Boston’s most delicious and innovative breweries, Harpoon, puts on an annual Octoberfest that is simply delightful. Spend the better part of two days eating and drinking, but mostly drinking.

fall boston


Fall Themed Tours

Aside from the above-mentioned organized festivals, there’s plenty more to entertain during the fall in Boston. Since the weather is so fine and the foliage so scenic, it’s extra fun to join in on a fall foliage tour, in which you’ll be treated to the most spectacular, secret, foliage spots in and around the city. Other seasonal tours we recommend include:

-Ghost Tour in Harvard Square

-Pirate Ship Tour

-Titanic Masquerade

Getting out and about to enjoy the crisp cool air and city scenery is delightful, and sprinkle in a few fall events here and there and you’ve got the recipe for a perfect autumn weekend in Boston. The only other detail you’ll want to carefully consider is where to stay. Every trip to Boston is enhanced by the simple act of selecting a hotel that is centrally located. Nestled perfectly in the heart of Copley Square lies the Copley Square Hotel. Minutes from iconic attractions such as Boston Common the Public Garden, Copley Square Hotel is perfectly situated for you to enjoy all the fall festivities in the city!

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