Best Things To Do In Boston In The Fall

Headed to Boston this fall? It won’t be hard to fill your schedule: Boston is chock-full of fantastic fall fun.

By Kim Knox Beckius

Aug 20 2023


Fall foliage frames the Boston skyline from across the Charles River.

Photo Credit : Danica Chang

As Boston’s parks, riverbanks, and tree-canopied streets brighten with fall colors, the Massachusetts capital city is as lively and picturesque as it ever gets. College students have returned. Pumpkins appear on brownstone doorsteps. And Octoberfest beers are on tap in every bar. If you’ll be spending time in Boston this fall, or if you need a nudge to get there while vibrant leaves hang on—often through early November—we’ve got 10 suggestions for embracing the city’s spooky history, culinary and cultural scenes, sports traditions, and autumn splendor.

1. Explore the Arnold Arboretum of Harvard University

Billing itself as a “museum of trees,” the oldest public arboretum in North America is a fine place for a fall stroll. With landscapes designed by Frederick Law Olmsted and 16,000-ish plants from around the world, these 281 acres invite visitors to contemplate nature’s diversity and to celebrate this season of transition. Curated groupings of tree species put on quite a show as fall foliage colors peak. Free 90-minute guided tours are offered frequently through mid-November, and the Arboretum’s calendar also features programs that range from mushroom walks to meditation sessions in the shade of stately maples.

2. Tingle Your Spine on a Haunted Boston Ghost Tour

There’s no better way to experience Boston than on foot, and that goes for the city’s spooky and seamy side, too. So, join Haunted Boston Ghost Tours for one of their 8 p.m. walks into the shadows, where tales of murder, lust, vengeance, and ghastly doings will entertain you and, quite frankly, creep you out. Step out into the night from the entrance to the Central Burying Ground, and keep a watchful eye for ghosts as your guide masterfully weaves stories of Boston’s gruesome history.

The Head of the Charles Regatta
Photo Credit : Massachusetts Office of Travel & Tourism

3. Cheer for Rowers at the Head Of The Charles Regatta

The one “must” among the multitude of events held each fall in Boston is the Head of the Charles Regatta: the world’s largest three-day rowing competition. Always the second-to-last full weekend in October, this tradition, which dates back to 1965, draws spectators to both banks of the Charles River. In addition to rooting for more than 11,000 rowers from around the globe, competing as individuals and teams, you’ll be able to participate in myriad activities, from trying out a rowing machine to sampling local food to shopping at vendor booths.

4. Marvel at an 80-foot Giraffe and More Amazing Lanterns

One of Boston’s newer fall traditions, Boston Lights: A Lantern Experience illuminates Franklin Park Zoo’s 72 acres with a menagerie of fantastical creatures and other enormous constructions. There’s a story behind every lantern installation: A display devoted to ancient Egypt’s pyramids and awe-inspiring wildlife was developed, for example, in partnership with the Museum of Fine Arts, Boston to ensure historical accuracy. On your lantern walk, you’ll also be dazzled by an ice-breathing dragon and a coral reef populated with marine life from Down Under. In homage to China’s rich cultural history, you’ll also see a 200-foot-long display of pagodas, cranes, and lotuses and walk through an 80-foot-long glowing dragon tunnel.

The pumpkin patch at the Anchor.
Photo Credit : The Anthem Group

5. Eat, Drink, and Pose for Pics at New England’s Largest Urban Pumpkin Patch

Each fall, the Anchor trucks in upwards of 15,000 pounds of pumpkins, turning this outdoor entertainment and gathering spot at the Charlestown Navy Yard into the largest urban pumpkin patch in New England for most of October. Head to this waterfront venue for drinks, light bites, and a full calendar of free community happenings including live music, Latin dancing, comedy nights, and game watch parties. The pumpkins in your photo shoots—except maybe the giant ones—go home with Boston children to brighten their Halloween.

6. Go Back to College

Boston is New England’s biggest college town. Even if you’re not an alum of one of the prestigious institutions in Boston or neighboring Cambridge, fall is an excellent time to go “back to campus” for a tour or an event. Some suggested things to do: Tour Harvard or the MIT campus with a current student for insights into the history and traditions of these famed universities; tailgate and attend a Boston College football game; or hear Berklee College of Music students perform (many shows are free). If you’re a current college student with a valid ID, don’t miss the free annual CollegeFest Boston at Fenway Park.

7. Savor Fall Treats at the Boston Public Market

The flavors of fall await at the Boston Public Market: a food hall where everyone in your group can order exactly what they’re craving. Once there’s the slightest chill in the air, you’ll want to rush to Red Apple Farm’s stall for all of the fresh products they grow, make, and bake just 90 minutes west of the city in rural Phillipston, Massachusetts. We’re talking about fresh-pressed cider, Cider Bar drinks, caramel popcorn, fudge, and many varieties of apples. Plus some of the best warm cider donuts you’ve ever tasted, made before your eyes by the donut robot. The ultimate fall food celebration, the Boston Public Market Harvest Party, benefits the Community Engagement Fund. As you sip and sample, you’ll be helping to sustain the market’s small businesses and its free educational offerings for visitors and the community.

The Boston Tea Party Ships & Museum
Photo Credit : Massachusetts Office of Travel & Tourism

8. Toss Tea in the Harbor

The Boston Tea Party Ships & Museum is one of the city’s most interactive attractions. Why visit this fall? The 250th anniversary of the Boston Tea Party, the best-known protest in American history, is coming up on December 16, 2023, so now’s the time to beat the crowds and to reacquaint yourself with the patriots who boldly stood up to taxation by the British. You’ll even get to portray one of these heroes on your tour, which ends with a ship boarding and reenactment. An extra reason to visit in the fall? Abigail’s Tea Room is one of the coziest places in Boston to sip fresh-brewed tea, and the bottomless cup option allows you to sample all of the historic varieties.

9. Tour the Freedom Trail by Lantern Light

Been there, done that? If there = Boston and that = the Freedom Trail, you probably haven’t done it quite this way. The official Freedom Trail Lantern Tour revisits the red-lined path’s historic points and turns a macabre lens on the past. You’ll hear stories about witches and sword fights, visit a pirate’s grave, and follow in the footsteps of murderers. Led by a cloaked Freedom Trail Player, your tour is filled with true, researched accounts of Boston’s dark side. It’s a 90-minute experience that is decidedly not for kids under 12.

10. Sing Along on the Autumnal Equinox

Celebrate the arrival of fall as only Boston does. On the autumnal equinox, the annual Revels RiverSing brings Bostonians and other lovers of this glorious season to the banks of the Charles River for a mystical evening filled with pageantry. It’s a family-centric event complete with street bands, choirs, costumes, dancing, and opportunities to join your voice with others’ in a ritual that honors this day of roughly equal light and darkness.

What’s your favorite thing to do in Boston in the fall?