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10 Boston Activities to Do in and Around the City This Fall (2022)

Scarecrow in a pumpkin patch

Are you new to Boston? Did you recently move into a new apartment in the city? Or are you a long-time native and just want some new ideas of activities to do in and around the city this fall? If you answered yes to any of these questions, keep reading! Our team at Rentwise Boston has come up with a list of our top 10 favorite activities that you need to try in the Boston area in 2022.


Go Apple Picking

Sign for "Honey Pot Hill" apple orchard in Stow Massachusetts

Going to a farm to pick apples is a classic Boston activity in the fall, as the fruit goes extremely well in Massachusetts. Some apple orchards in the Boston area include Honey Pot Hill Orchards in Stow, Carlson Orchards in Harvard, and Carver Hill Orchard, which is also in Stow.

Go Shopping on Newbury Street

Shoppers walking down Newbury Street in Boston

Newbury Street is a premier shopping district in the Back Bay with hundreds of shops for people of all ages and budgets. Along with the great shopping, the street is lined with gorgeous brownstone buildings and is decorated for fall with pumpkins and naturally occurring foliage on the trees.

Get Drinks at a Beer Garden

Hands making a toast cups of beer from Trillium Brewery

The crisp fall weather in Boston is the perfect time to sit outside and enjoy a nice drink at one of the city’s many beer gardens, given you are 21 or older, obviously. Trillium Brewery in Fenway and Cisco Brewery in the Seaport are two of our favorite spots.

Visit a Playground

Entryway arch for Tadpole Playground in Boston

As opposed to #3 on our list, which is an activity only for adults, #4 on our list is to take a family visit to one of Boston’s many playgrounds. There are lots of beautiful playgrounds in Boston where your kids can play. Tadpole Playground in Boston common is our favorite.

Take a Food Tour

Dinner table with Italian food and wine

Boston is home to many amazing restaurants and food you need to try on your next day off. You can go to the North End for classic Italian food and desserts, a trendy, new restaurant in the Seaport, or to the Boston public market to enjoy some local, farm-fresh, seasonal foods.

Take a Trip to Salem

Salem witch house decorated with pumpkins

Only 45 minutes away from Boston, Salem, Massachusetts, is one of the spookiest towns in the country. As the site of the infamous colonial Witch Trials, the town celebrates its history by hosting extravagant Halloween events throughout the month of October, so if you really want to get into the spooky season, you need to make this trip.

Go Whale Watching

Whale tail breaching in the ocean

As a coastal city, Boston offers a lot of Whale Watching excursions. The boat tours are an all-day trip and are a fun way to spend a beautiful fall day out in nature.

Hike at Blue Hills

View of foliage and the Boston Skyline from Blue Hills Reservation.

If you like to hike or are a lover of the outdoors, you need to go hiking at the Blue Hills. This nature reserve is located in the suburb of Milton, which is a quick trip outside the city. The site offers many attractions, including a miniature zoo, pristine woods to enjoy the fall foliage, and views of the Boston skyline at the top.

Enjoy the Foliage

Foliage and pond in Boston Common

Massachusetts is home to some of the nation’s most beautiful foliage. This natural wonder can even be observed right within Boston’s city limits. Some of our favorite ways to enjoy the foliage views include taking a trip to the public garden, riding around the city on a rented blue bike, or taking a boat ride on one of the city’s many harbor cruises.

Attend a Professional Sports Game

 Boston Celtics Basketball game at TD Garden

The fall is prime time for New England sports fans, as the Boston Red Sox, Patriots, Bruins, and Celtics are all in season. So, if you are a sports fan, the fall is the perfect time to visit Fenway Park, Gillette Stadium, or T.D garden and watch a professional sports game.


Looking got a new home?

Ultimately, if you are not a Boston native, and would like to move into the city to try some of these seasonal activities, check out Rentwise Boston to find your new apartment!


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