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Published September 12, 2023

Boston's Ultimate 2023 Fall Bucket List

Pull on a sweater and grab a Pumpkin Spice Latte—fall has arrived in New England. 🍁🎃

by Boston Bucket List


As autumn arrives—with golden hues but not-yet freezing temperatures—Boston comes alive with a smattering of activities and things to see and do. From street fairs and walks through the changing leaves, to whale watching and cranberry bog tours, New Englad's biggest city has no shortage of options when it comes to fall experiences.

To make it easy, we gathered a list of the city’s best autumn activities so you can make the most of sweater-weather season. Here's everything to see and do in Boston this fall!

17 Things to Do in Boston This Fall

Stroll Through the Fall Foliage

No one does fall colors like New England, and now is the time to take it all in. You can see the changing leaves almost anywhere you go in Boston, but there are a few spots that are especially picturesque.

At Beacon Hill, you’ll see historic brick buildings adorned with colorful ivy and falling leaves. Stroll through the cobblestone streets to continue your leaf-peeping at Boston Common, where you can revel in the golden hues of the trees and enjoy a leisurely picnic. And don't miss the Boston Public Garden, where the swan boats glide beneath a canopy of red and gold.

Where: Various locations.

Go Apple Picking at Brooksby Farm

Fall at Brooksby Farm means that crisp autumn air, hayrides and cut-your-own-flower bouquets are in season. Plus, plus campfires and s'mores are available on select weekends, and—of course—the apple orchard is abundant. Come for the apple picking, and don’t skip the apple cider donuts from the farm store on the way out. 

Where: 54 Felton St, Peabody, MA
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Spectate at the Head of the Charles River Regatta

See world-class rowing at the Head Of The Charles Regatta on October 20–22, where the best crews from around the world converge on the scenic Charles River. Reunion Village is where alumni and spectators gather to support their favorite teams, and the Weld Exhibition is the go-to for great local grub and Regatta merchandise. Feeling inspired? Visit the Rowing and Fitness Expo at the finish line to test out a rowing machine or browse vendor merchandise to take home.

Where: 2 Gerrys Landing Rd, Cambridge, MA
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Celebrate Oktoberfest at Harvard Square

Experience the 43rd Annual Harvard Square Oktoberfest on October 9, when the streets come alive with vibrant chalk art, live music, and the renowned HONK! parade. Celebrate with the festival’s delicious food, traditional beer gardens (plus a new wine garden this year), and one-of-a-kind goods sold streetside. While there’s a raucous six stages of music, don't miss the signature 1 PM HONK! Parade, featuring over 20 bands horn-tooting, hand-clapping and foot-stomping away.

Where: 18 Brattle St, Cambridge, MA
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Sip Premier Spirits at WhiskyX Boston

Hosted by Paul Janeway of St. Paul and the Broken Bones, indulge in the finer things in life at this premier whiskey tasting and music festival on September 15! Taste, discover and learn about over 60 spirit brands and cocktails available, plus enjoy a chic cigar lounge and a delicious food truck village.

Where: SoWa Power Station: 550 Harrison Ave, Boston, MA
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550 Harrison Ave, Boston, MA 02118, USA
WhiskyX Boston
Starting at $50

Book now


See the Pumpkin Flotilla at Frog Pond

See hundreds of glowing jack-o-lanterns float on the water at the annual pumpkin flotilla. Guests can bring their own small carved pumpkins to contribute, and are invited to judge the creatively carved jack-o-lanterns from various local organizations. The costume-encouraged, family-friendly event will also include performers, music, and child-focused activities!

Where: 38 Beacon St, Boston, MA
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Go Whale Watching

Join expert marine biologists on a catamaran that will whoosh you across the Boston Harbor to see finbacks, minkes, pilot whales, and more! The diggs are comfy too, with three outside viewing decks and a climate-controlled interior cabin with cushy seats and a snack bar. 

Where: 1 Long Wharf, Boston, MA
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1 Long Wharf, Boston, MA 02110, USA
Tickets for Boston Harbor Whale Watch Cruise
Starting at $68

Book now



Party at South Boston Street Fest

Enjoy a day of excitement at the 23rd South Boston Street Fest. It will feature 100 local businesses, non-profits, artists, and your favorite restaurants. The lineup is incredible, including Thomas Park, Houston Bernard, Guilty Pleasure, and the Late Risers. Bring the kids for a day filled with princesses and pirates, balloon twisters, and caricature artists—along with Barbie photo backdrops for the young at heart!

Where: East Broadway, between I and L Streets, Boston, MA
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Tour Fenway Park

Fall may mean the start of football season, but it's also the start of baseball's playoff season. As the oldest MLB stadium in the league, Fenway Park has gone through substantial updates, which you can hear all about on this true fans tour. You’ll see the infamous Fisk and Pesky Poles, sit atop the massive Green Monster wall, and admire the size of the grounds where giants of the sports have played. Learn about pennant-winning home runs, World Series games, championships, and iconic retired numbers.

Where: Fenway Park: 4 Jersey St, 02215, Boston, MA
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Fenway Park, 4 Jersey St, Boston, MA 02215, USA
Tickets for Fenway Park: Guided Tour
Starting at $25

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Attend the Boston Book Festival

Celebrate the power of words at Boston’s annual book festival on October 14! Join hundreds of fiction, nonfiction, YA, and kids authors for a day of readings and discussions, book signings, and lively literary events. The BBF will also feature kids activities, walking tours, food trucks, and more. It’s the perfect place to find your new favorite book and curl up with a fall-flavored latte and oversized blanket.

Where: Copley Square, Boston, MA
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Visit a Pumpkin Patch

It’s pumpkin patch season, and we suggest making it an entire experience by going to The Lookout. Along with the patch, guests can enjoy slow cooked BBQ and comfort food, farm-to-glass beer, cider or wine, a two-acre corn maze, farm animals, and more. They’ll even serve delicious pumpkin flavored treats, like pumpkin spiced donuts and pumpkin and cranberry waffles tou round out the full fall experience.

Where: 89 Pleasant Street, Natick MA
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Chow Down at the Boston Local Food Festival

For one glorious day a year, SBN transforms the historic Boston waterfront into the nation's largest local and sustainable food hub! This year's festival kicks off on September 17 and showcases farmers, local restaurants, food trucks, fisher folks, and organizations all focusing on healthy food and fitness from New England. The BLFF also features lively chef and DIY demos, a seafood throwdown, diverse music and performances, and a family fun zone!

Where: 99 Bishop Allen Dr, Cambridge, MA
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Grab Seasonal Goodies at Union Square Donuts  

Originating from a brioche dough, Union Square donuts have a light and airy texture, all crafted with house-made glazes, jams and creams. Fall is made complete with a regular sampling of their seasonal flavors that include the pumpkin maple praline roll, caramel apple cream bar, salted brown butter cruller, and even a vegan chai apple cider donut—just to name a few.

Where: 33 South St, Somerville, MA
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Trick or Drink Through Halloweekend

What's the adult version of trick or treating? Trick or drinking, of course! Barcrawlerz features the best drink specials and bars in town, and Trick or Drink gets you into any of the participating bars with no cover, and drink specials all night. Just check in at Back Bay Social to get your wristband and map with participating bars, and have fun!

Where: Back Bay Social: 867 Boylston Street Boston
More information


867 Boylston Street, Boston, MA 02199, USA
Trick or Drink: Halloween Bar Crawls - Boston
Starting at $15

Book now


Attend Topsfield Fair

Enjoy the quintessential New England fall experience at the Topsfield Fair complete with a giant pumpkin weigh-off! This is the country's oldest agricultural fair, dating back to 1818 and will run from September 29 through October 9 this year. Revel in the charm of this classic event, featuring everything from thrilling rides and carnival games to live music and jaw-dropping agricultural exhibitions.

Where: 207 Boston St, Topsfield, MA
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Tour a Cranberry Bog

Celebrate Massachussetts' official state berry with a visit to a crimson bog! While located outside the city, it makes for a fun daytrip, and guests can tour the cranberry bog and even dive in, before hauling home some fresh-picked produce! Cape Cod Cranberry Growers' Association takes groups on rented school buses to their crimson floating berries, and stops at the mini store filled with cranberry products and fresh local berries for sale.

Where: 265 S. Meadow Rd., Plymouth, MA
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See the Spooky Halloween Decor of Beacon Hill

The residents of Beacon Hill go all out with Halloween decor. Intricate cobweb draping, floating ghosts and towering skeletons, and endless lines of jack-o-lanterns all adorn the charming homes of the historic neighborhood, making it a vibrant spooky realm to tour and sightsee throughout October. Make sure to find the most elaborate houses on Mount Vernon, West Cedar, Pinckney St. and Louisburg Square!

Where: Beacon Hill, MA


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