13 Cool Things to Do in Boston This Fall

Pumpkin patch visits, spooky road trips, and more fall fun.

Head of the Charles Regatta
Head of the Charles Regatta | Keith J Finks/Shutterstock
Head of the Charles Regatta | Keith J Finks/Shutterstock

While saying goodbye to summer is always bittersweet, just remember that fall happens to be one of the best—if not the best—seasons in New England. Favorite activities from the previous season like outdoor dining and rooftop drinking are still within reach, and the Boston area hits its stride as the weather cools off with premier foliage views and lots of spooky activities.

All this to say, Boston is where you want to be in the fall. We’ve rounded up the top things to do all season long from breathtaking hikes and local road trips to scenic apple orchards and Halloween festivities, so keep reading for more inspiration.

The Witch House in Salem
The Witch House in Salem | Georgios Antonatos/Shutterstock

Salem, Massachusetts
This one’s a given, but there’s no better place to visit in New England during the fall season than Salem. Soak in the town’s frightening and eye opening history by taking a tour with the folks at Bewitched After Dark and make sure you stop in the historical Hawthorne Hotel, which the cast of the sitcom Bewitched enjoyed their stay at back in the ‘60s and ‘70s. Another worthwhile stop, among many, is the Ropes Mansion AKA Allison’s House in Hocus Pocus, where you can peruse the backyard’s 5,000 square-foot garden. Not to mention the town’s long list of dining options from Bella Verona to The Ledger, go-to breakfast joint Ugly Mug diner, and if you’re looking to stay in and cook, Jean Louis Pasta Shop is a must.

Parlee Farms
Parlee Farms

Various locations
There are fewer things more wholesome than a day spent apple picking. Now throw a New England backdrop into the mix and you’re golden. From North Andover’s Smolak Farms to Stow’s Honey Pot Hill Orchards, we’ve got you covered with our list of the best farms near the city for apple picking.

The Envoy Hotel, Autograph Collection
Lookout Rooftop and Bar | The Envoy Hotel, Autograph Collection

Various locations
Although the temperature is starting to dip, it’s not the end of rooftop season just yet. Plus, what’s better than a fall outing spent outside beneath the stars? Dorchester Brewing Company’s Rooftop Hopservatory, which overlooks the Boston skyline offers up both indoor and outdoor rooftop seating while the third floor promenade deck at Seaport’s Legal Harborside happens to open throughout the year. There’s also Rooftop@Revere at the Revere Hotel Boston Common, Seaport’s Lookout Rooftop and Bar at The Envoy (equipped with outdoor firepits), Contessa’s year-round rooftop dining atop The Newbury Hotel in Back Bay, and roofdeck walk-ins available at South Boston’s Six\West.

Bow Market
Bow Market

Check out one of many local open-air markets

Various locations
Fall is for the farmers markets and outdoor pop-ups, and Boston has no shortage of the two. For local farmers markets, Copley Square (open through November 22) and Jamaica Plain (open year-round) have all the fresh and locally grown produce you need for a bounty of seasonal recipes. The farmers market in Haymarket (open year-round) tends to lean on the busier side but you won’t find better deals—plus, it’s one of the oldest in Boston. For entertainment and arts shops, you can’t beat Union Square’s Bow Market (open year-round) and Seaport’s SoWa Open Market (open until October), which also has a year-round Vintage Market located downstairs at 450 Harrison Avenue on Sundays.

Everett
Known as the largest five-star resort outside of Las Vegas, the Encore Boston Harbor hotel has already earned its accolades with only a few years under its belt. You can go for a luxurious stay along the water alone, but most of the other visitors will be feeling lucky as they visit one of only three full-service casinos in Massachusetts.

Bleacher Bar
Bleacher Bar

Take yourself out to the ballgame

Fenway and Kenmore
Catching a Red Sox game is always a treat—and there’s still time to catch a few more home games. Speaking of treats, Fenway Franks and draft beers are ballpark must-haves, but you’d be surprised at the number of delicious options around Fenway worth checking out before or after a game. Choose from Fenway’s Loretta's Last Call, Bleacher Bar, and Eventide Fenway, and for even more ideas, check out the best places to grab a pre-game bite around Fenway.

Or see the Bruins and Celtics at TD Garden

Downtown
Colder weather means basketball and hockey means sitting courtside and heading to the rink, so buckle up for the upcoming Bruins and Celtics fan fare. And with the North End right next door, you might as well make it a whole night and make a reservation at some of the beloved Italian restaurants like Giacomo’s, La Famiglia Giorgio’s Ristorante, Mamma Maria and Tony & Elaine’s. On the boozier side of things, there’s always the nearby West End Johnnie's, Tavern in the Square, Causeway, and Nightshift Lovejoy Wharf for an afternoon drink or night cap.

Hop on the ferry to Spectacle Island

Spectacle Island
With more than 114 acres to explore, Boston’s Spectacle Island has plenty in store for a quick weekend day trip. The 30-minute ferry ride brings you to the nearby hiking destination featuring a signature panoramic view of the harbor atop North Drumlin. The ferry’s fall schedule runs now until October 10, and returns in the spring.

Boston Seaport
Boston Seaport

Seaport
Before you’re summoned to indoor workouts and virtual classes, get your fix of fresh air with Boston Seaport’s free outdoor fitness series on Seaport Common. The classes, which are happening now until the end of September, feature everything from mindful warrior yoga to zumba to pilates. All-levels are welcome.

Museum of Fine Arts, Boston
Museum of Fine Arts, Boston

See a world-class art exhibit before it’s too late

Various locations
Boston has some of the best museums in the country—if not in the world—from the Isabella Stewart Gardner Museum to the Museum of Fine Arts Boston. While some historic art collections and pieces might be on permanent display, the city is also rife with buzzworthy exhibits that are only in town for a limited time. For more on which exhibits to check out before it’s too late, read our roundup of the top museum exhibits to visit in Boston right now.

Brattle Book Shop
Brattle Book Shop | NoyanYalcin/Shutterstock

Downtown Crossing
One of the city’s best-kept secrets (unless you happen to routinely walk past on your way to Park Street), Brattle Book Shop’s outdoor sale lot continues throughout the fall. Located directly next to the book shop on West Street, the outdoor lot is tucked in an alley with stacks on stacks of selections. Not to mention it’s quite the sight for some quality snapshots of the city’s unique offerings.

Lamplighter Brewing Co.
Lamplighter Brewing Co.

Various locations
The city and its surrounding neighborhoods have plenty of breweries worth checking out including Downtown Crossing’s Democracy Brewing, Seaport’s Harpoon Brewery, Fort Point’s Trillium, Somerville’s Aeronaut Brewing Co., Cambridge’s Lord Hobo, and JP’s Turtle Swamp Brewing and Sam Adams Brewery. But there are a couple of semi-newbies to add to your list as well, like Lamplighter Brewing Co.’s CX taproom located near the Lechmere T stop and Roxbury’s Flying Embers Brewery & Social Club, which originally hails from California.

White Mountains
White Mountains | haveseen/Shutterstock

Take a hike

Various locations
New England is home to a million dreamy hiking destinations. And if you’ve been waiting for a fall adventure, we’ve got the places for you. If you’re looking to stick around, Halibut Point State Park in the seaside town of Rockport is a gem or the Aquinnah Cliffs Overlook in Martha's Vineyard. But if you’re up for the drive and something a bit more advanced, you can head to Acadia National Park in Maine (about a five-hour drive), White Mountains in north-central New Hampshire and western Maine (about a three-hour drive), or Mount Mansfield in Vermont to name a couple.

Boston Public Garden
Boston Public Garden | Keith J Finks/Shutterstock

Explore the Emerald Necklace

Various locations
If you’re looking for something a bit closer to home to achieve an elevated seasonal stroll, look no further than Boston’s Emerald Necklace, the city’s largest park system designed by landscape architecture legend Frederick Law Olmsted. With trails from Back Bay to Dorchester, you can get your steps in without traveling too far. And arguably one of the most beloved parks within the Emerald Necklace, the Arnold Arboretum provides a gorgeous view of the city skyline.

Friday, October 21 – Sunday, October 23
Cambridge
The Regatta, which was first established in 1965, is back and kicking off Friday, October 21. Watch as the top rowers (roughly 11,000 athletes) in the world compete in the three-mile race on the Charles River. Snag a spot along the esplanade, surrounded by Boston’s peak fall foliage, for a gorgeous afternoon. For information on events going on around the Regatta and the best locations for spectators, visit the official website.

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Jillian Hammell is a contributor for Thrillist. You can follow her on Instagram.