Boston Massachusetts in the Fall: 12 Best Experiences

August 24, 2022

Cheering on the New England Patriots* at Gillette Stadium, sipping on cider as you stroll through Faneuil Hall, and leaf peeping on the Freedom Trail. Boston in the fall is about as picturesque as it gets! 

Follow along to discover how to have a great time in Boston this fall!

Learn about the spirited tea-themed events of Boston Harbor, or indulge your craving for spooky stories with a Ghost and Gravestones tour.

Whether you seek a historical trolley tour or an ice-cold pint of Sam Adams lager, The City on the Hill is overflowing with fall festivities. 

From apple-picking juicy Galas and Macintoshes to tranquil visits to Walden Pond, autumn is the ideal occasion to uncover the hidden gems of Beantown. 

Don’t wait; take advantage of all the fantastic things to do in Boston in the fall! 

Best Time to Visit Boston in the Fall

Curious about when is the best time for fall colors in Boston, or perhaps unsure of how to pack for your autumn getaway? The City on the Hill boasts cool, crisp temperatures from September through November. Expect highs of 70 degrees during the day in September, with lows in the high 50s at night. By November, temperatures dip in the 50s during the day and high 30s at night.

Related Post: Upcoming Events and Festivals in Boston

Solve the problem of what to wear in Boston in the fall by packing plenty of sweaters and a light jacket. Try to plan a visit from late September through the end of October for optimum fall foliage in vivid hues of amber, vermillion, and ochre. This will allow you ample time to observe the changing Japanese Maples, Sweetgum, and Ash trees. 

Paul Revere Statue outside the Old North Church, Boston, Massachusetts

Paul revere Statue and the Old North Church, Boston, Massachusetts

Boston Hotels

Dreaming of a day trip to the Boston Common? Or want to stroll through the brick-laden sidewalks of Beacon Hill?

Whatever your Beantown desires, make the most of your stay in the Athens of America when you book one of our elite Boston Hotels.

From luxury accommodations just steps from the Freedom Trail to boutique lodgings by Back Bay, we offer options for every traveler. 

photo credit: Club Quarters Hotel Faneuil Hall, Boston via Facebook

Day Trips from Boston in the Fall

Visit Walden Pond

Calling all bookworms! Combine your love of literature with the ambiance of the great outdoors when you plan a day trip to Walden Pond. Located less than an hour from Boston, this National Historic Landmark is the famed site where Henry David Thoreau wrote his opus, Life in the Woods.

Related Post: 13 of the Top Things to Do in Boston at Night

Run by the state of Massachusetts, the reservation comprises over 330 acres of lush wooded trails and a serene 102-foot-deep glacial kettle-hole pond.

The harvest season illuminates the natural beauty of Walden, making it the perfect time for an afternoon hike, canoe, or fishing trek.

Bring along that camera to document the arresting autumnal hues, and be sure to tour the replica of Thoreau’s one-room cabin. 

photo credit: Only In Massachusetts via Facebook

Visit Providence

Venture outside the confines of the Cradle of Liberty when you head to the Ocean State. Come fall time, Providence, Rhode Island, is awash in New England charm. Take in the classic architecture of Brown University, visit Federal Hill, or take a ride on an authentic river Gondola.

Foodies will be in heaven when they break bread in one of the country’s most revered Little Italy, while historians will be drawn to the colonial past of the East Side. Take in a Broadway show, shop for antiques, or embrace the animal adventure of the Roger Williams Park Zoo.

Visit Salem, Massachusetts 

Double, Double toil and trouble. Prime yourself for a very witchy journey when you tackle the 25 miles from Boston to Salem, Massachusetts. Do a deep dive into the infamous witch trials when you tour this colonial city. Fans of the occult will love the festive spirit of Salem in October.

Related Post: 3 Days in Boston: How to Make the Most of 72 Hours

Learn all about the 17th-century trials, visit the Witch House, and explore the Old Burying Point Cemetery. Then, wander through Salem’s cobblestone streets and stop at the Salem Witch Museum for a narrated tale of the witch hysteria. Or, visit the House of the Seven Gables to witness author Nathaniel Hawthorne’s literary inspiration.

For an extra dash of spooky flavor, sign up for a candlelit ghost tour, or visit the numerous filming locations of the beloved spooky flick, Hocus Pocus. 

photo credit: Downtown Salem via Facebook

Best Things to Do in Boston in the Fall

Boston Old Town Trolley Tour

Ready to maximize your time in the Cradle of Liberty? Climb aboard a Boston Old Town Trolley Tour and cover every inch of Beantown. Stop by the Boston Public Garden, snap a selfie at the Cheers bar, or journey under the sea at the New England Aquarium.

Related Post: Boston Historical Sites: 21 Must-See Stops for History Buffs

See Boston at your own pace as you hop on and off at will. Enjoy live narration while reveling in some of our Nation’s most historic sites, including Faneuil Hall, the Boston Tea Party Ships & Museum, and Beacon Hill.

Delight in the charm of Charles Street, spot the Old State House or marvel at the massive public library. Choose from one or two-day options, and discover the quality, professionalism, and pleasure of an Old Town Trolley Tour.

photo credit: Charles Street: Our Main Street via Facebook

Boston Tea Party Ships & Museum

Steep yourself in one of the most pivotal American History events when you visit the Boston Tea Party Ships & Museum. Located in the Boston Harbor, this immersive museum experience is packed full of interactive exhibits, costumed actors, centuries-old artifacts, and more.

Witness rousing reenactments of that fateful night in December 1773. Travel down Griffin’s Wharf, board colonial ships, and even practice throwing your own tea into the icy waters of New England. Then, sneak a peek of the Robinson Tea Chest. The only known surviving tea chest from the protest, or sip on a piping hot cup of Darjeeling in the Tea Room.

Want to learn more? Check out our in-depth guide to the Boston Tea Party.

View of historical reenactment of tea being poured in the Boston Hard from a Boston Tea Party Ship in Boston, Massachusetts, USA

photo credit: Boston Tea Party Ships & Museum via Facebook

The Freedom Trail & Boston's North End Walking Tour

Colonial heritage, immigrant culture, and plenty of rousing American Revolution heritage. The city of Boston is chock full of fascinating stories and historical sites. Relish the expert knowledge of a skilled local guide when you tackle The Freedom Trail & Boston's North End Walking Tour.

Related Post: Getting Around Boston: The Ultimate Guide for Any Visitor

This two-hour adventure is the ideal introduction to the Athens of America. Stroll through the sparkling stretches of the Boston Common, swing by the Paul Revere House, or pay your respects at the Granary Burying Ground. Under this hallowed soil, the remains of Revolutionary heroes like Samuel Adams and Paul Revere rest.

Cover over a dozen attractions of interest, including King’s Chapel, the Old North Church, and the Boston Massacre grounds. Round out your comprehensive tour in the North End, a neighborhood renowned for its Irish and Italian immigrant heritage. 

exterior of faneuil hall with crowd of people outside and street lamps on a sunny day in boston, massachusetts, usaBoston Ghosts and Gravestones Tour

Poltergeists, serial killers, and haunted houses, oh my! Uncover the macabre side of Beantown when you join your sinister host for a Boston Ghosts and Gravestones Tour. Spend 1.5 hours revisiting the supernatural and blood-curdling stories of Boston’s past.

Hop aboard the ghost trolley, and speed away to two of the oldest burial grounds in Boston. Let your cursed guide regale you with stories of real-life demons, including the Boston Stranger and the ‘Angel of Death,’ Jolly Jane.

View gravestones, stop by the site of the Boston Common public hangings, and muster the courage to see B-town’s most haunted hotel. From the grave robbing scandals to involvements with the Salem Witch Trials, the Puritan City is a hotbed of occult activity.

photo credit: Ghosts & Gravestones Boston via Facebook

Boston Fall Events & Festivities

Head of the Charles Regatta

A Beantown fall tradition almost as famous as a Patriot’s game, for over 60 years, rowers and spectators have flocked to Boston for the Head of the Charles Regatta. This competition is the world’s largest Regatta and attracts experienced rowers far and wide. An equally festive experience for spectators, viewers can watch the race commence at the DeWolfe boathouse.

Related Post: When is the Best Time to Visit Boston?

For additional awe-inspiring views, head to the Eliot Bridge Enclosure. Fuel up on snacks and drinks at the Weld Exhibition, or show your team support at the Reunion Village. Finally, witness the epic conclusion of the race at Herter Park, which boasts the Finish Line bollards installed in 2016.

Looking for the most unique things to do in Boston? Check out our guide to discover the surprising side of this colonial city!

photo credit: Head Of The Charles Regatta via Facebook

Beer Gardens

Summer may be long gone, but you still have a smidge of time left to soak in the rays at one of Boston’s resplendent beer gardens. So mosey on over to the Esplanade or Greenway to enjoy a refreshing brew al fresco before they close for the season.

Check out Trillium Brewing for a toasty Stout or hearty ale pour. Bring your appetite, as you’ll want to indulge in the variety of food truck eats. Then, for some refreshment around the Esplanade, imbibe with Owl’s Nest, whose multiple outdoor beer garden locations have created quite the stir. Sample juicy IPAs, light lagers, and fruit-forward sour ales. 

photo credit: Trillium Garden on the Greenway via Facebook

Samuel Adams Boston Brewery

Yearning for a true Beantown beer experience? After a day of lush leaf peeping at the Arnold Arboretum, swing by the Samuel Adams Boston Brewery. This iconic Boston locale is located near Jamaica Plain and serves up equal parts history and suds. For almost 40 years, this uniquely Boston brand has delighted locals and visitors with their dedication to their craft.

Enjoy a full brewery tour experience, sip on some Pilsners and Porters, or enjoy beer yoga. In addition, fall time guests should squeeze in some time for the annual Boston Oktoberfest celebration. From September 23rd through the 25th, the brewery will be transformed into a traditional beer hall featuring live music, stein hoisting contests, food specials, and German-inspired beer releases.

photo credit: Samuel Adams via Facebook

Columbus Day Parade

The City on the Hill’s annual Columbus Day Parade will not be taking place this year. Traditionally this spectacular celebrates Boston's Italian heritage and Christopher Columbus' expeditions to the Americas.

Related Post: Pet-Friendly Boston: Hotels and Restaurants, 

Usually held the Sunday before the holiday, this year, a special Heritage Day event will be held instead. More details regarding this event have yet to be announced. 

Apple Picking 

Glistening Gala, Honeycrisp, and McIntosh apples are almost too pretty to eat! Pick as many red beauties as you can handle when you trade in Beacon Hill for some farm-flavored fun. Take a trip to Tougas Family Farm for over 30 varieties of apples.

Load up on Ginger Gold, Sansa, Suncrisp, and more before you treat yourself to an Apple Cider Donut Sundae from the Farm Kitchen. For an even more convenient apple adventure, cruise just 30 minutes outside the city to Dowse Orchards. A legacy farm with over 200 years of history, they are proud to offer plenty of apples, fresh cider, and their own line of homemade preserves. 

photo credit: Tougas Family Farm via Facebook

Witches and warlocks, authentic Oktoberfests, and a world-class regatta. Boston in autumn is full of unexpected surprises. Depart from the Boston Harbor for a wind-swept whale watch tour, or hit the road for a Salem sojourn.

Lean into the B-town’s gruesome past, or celebrate the significance of Revolutionary War heroes like Paul Revere and Sam Adams on the Freedom Trail.

Celebrate the last vestiges of sunshine in an outdoor beer garden, or chow down with Italian eats in the North End.

Discover your harvest season desires when you visit Boston this fall!

Tell us, What Are Your Favorite Things to Do in Boston, Massachusetts, in the Fall?

Did we miss any of your Boston fall favorites? 

Leave us a comment below!

*Please note that the New England Patriots, Gillette Stadium, and the Company logo all fall under the registered trademark and/or service marks of the Company or its affiliates or licensors.


isis with mural in background

Written By Isis Maya

A New York native, Isis-Maya spent most of her professional life working in TV production until a vacation whisked her away to Central America and her love o ...

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