How to Have an Amazing Fall in Boston

An aerial view of colorful fall trees
Photo by Balazs Busznyak on Unsplash

If you’re new to the city, you’re likely wondering how to make the most of fall in Boston. In today’s blog, we’re going to share some of the city’s best fall activities so you can have a truly New England autumn. 

Tour the Boston Foliage

Known for its brilliant leaves, fall in Boston is beautiful in any part of the city. If you’re in the mood to see some especially beautiful foliage, you might walk around Beacon Hill, one of the quaintest and most historic Boston neighborhoods. Here you’ll find beautiful brownstones and fall leaves that will be sure to get you in the mood for autumn. 

Another great way to get outside in the city is the Rose Kennedy Greenway, a 1.5 mile stretch of greenspace between the North End and Chinatown neighborhoods. Stop by a beer or wine garden, sit on one of the huge porch swings, or check out one of the many great food trucks along the Greenway. The Greenway also offers scheduled events, such as the Chinatown Farmers Market, an Artisan Market, and even a moonlight tango class! 

For an escape from the busy city, try hiking through parts of the Emerald Necklace, a 1,000 acre stretch of connected parks throughout the greater Boston area. The Emerald Necklace runs through a number of Boston neighborhoods and offers convenient walking paths for residents. If you’re looking for a path near you, check out the map of the Emerald Necklace

The Arnold Arboretum, which is part of the Emerald Necklace, is another great place to get away from the bustle of city life and be alone in nature this fall. Also part of the Emerald Necklace is Franklin Park, the largest open space in Boston. Franklin Park also offers expansive woods perfect for a fall hike. Both of these parks are a great option for seeing the fall colors and getting some walking in!

Visit a New England Farm

What is more fall than picking apples, eating a cider donut, and getting lost in a corn maze? Luckily, New England has plenty of apple orchards and pumpkin patches to visit this autumn! Allandale Farm, located in Brookline and accessible by bus, is an excellent option if you don’t have a car in the city. In the fall, Allandale offers a variety of pumpkins and gourds, as well as apple cider donuts, garden plants, and fresh vegetables. 

Further out from the city, Connors Farm offers pick-your-own apple orchards, as well as a pumpkin patch, corn maze, and farm animals. With discounted tickets available for the weekdays, Connors Farm is a great place to have an outing with friends or a cute fall date! Starting September 28, you might join in the flashlight maize, a walk through the Connors Farm corn maze under the moonlight with no jump scares. If you’re more inclined for a spooky walk, they also offer a Haunted Corn Field event that’s perfect for spooky season! 

A line of apple trees with many apples fallen to the ground
Photo by Ana Essentiels on Unsplash

Located in Stow, Massachusetts, Shelburne Farm is another local favorite. Offering apple picking, pumpkins, a food truck, and apple cider donuts, this farm has it all! Plus, on the weekends, they have live music. Whichever farm you choose, apple picking and corn mazes are a must for your fall in Boston.

Take a Haunted Tour of Downtown

As we inch closer to Halloween, you may be looking for spookier activities around Boston. The city has plenty of ghost tours around downtown, both walking and via trolley. If you want or need to sit for most of the tour, the Trolley of the Doomed is a great option. While riding one of the quaint Old Town trolleys, you’ll get a 90 minute nighttime tour of some of Boston’s old cemeteries and most haunted areas. The tour also passes the Omni Parker House, Boston’s most haunted hotel. 

If walking is more your speed, check out one of the multiple haunted walking tours of the city. Boston Ghosts, the city’s top rated ghost tour, offers multiple different tour options, from a haunted bar crawl to a true crime tour of the city. Another popular choice is the Death and Dying Ghost Tour, which focuses on death and the afterlife in colonial New England. This tour is adults-only and pet friendly, so feel free to bring your furry friend! 

If you like to take things at your own pace, consider a self-guided haunted tour. With some tours priced as low as $5 per person, a self-guided tour is a great way to see the haunted sights of Boston on a budget.

Speaking of spooky, Boston is just a train or car ride away from Salem, Massachusetts. Famous for the Salem witch trials, Salem is a great place to visit during the fall. You might visit the town’s witch museum or take one of the many spooky walking tours available. About 40 minutes from the city by car or the commuter rail, Salem is a great place to take a day trip during your fall weekends.

Go Whale Watching

In Boston, whale watching season lasts through mid-November, making it a perfect fall activity. One popular whale watching tour is the New England Aquarium Whale Watch Cruise. Boston City Harbor Cruises partners with the New England Aquarium for this tour, so you’ll be joined by naturalists from the aquarium who can provide information about the marine life you see. This cruise also has a cash bar and both indoor and outdoor viewing spaces. The outing lasts 3-4 hours and visits the Stellwagen Bank Marine Sanctuary, which is a very popular area for whales to look for food, so you’re likely to spot some whales. Plus, the cruise starts from Long Wharf, which is within the city and accessible by subway. 

A whale jumping from the water
Photo by Todd Cravens on Unsplash

Another option for whale watching is the 7 Seas Whale Watch, which also visits the Stellwagen Bank Marine Sanctuary and offers on-board naturalists. This cruise starts in Gloucester, which is a 50 minute drive from the city. If you’re in the mood for a day trip, the 7 Seas Whale Watch is a great option!

Two pumpkins sitting in fall foliage. One is white and painted to look like a skull, and the other is orange with a black house and tree painted on.
Photo by Drew Hays on Unsplash

Attend Some Fall Festivities

Of course, it wouldn’t be fall without an autumn festival, and Boston offers many! Starting Friday, September 29, and running until Monday, October 9, the Topsfield Fair is a great way to celebrate fall in Boston. With rides, fair food, a parade, tons of farm animals, and live performances, this fair has all the quaint fall activities you could want. Accessible from the Commuter Rail or by car, you might take a weekend outing with friends to Topsfield!

Another huge fall festivity in Boston is the Harpoon Octoberfest, which is September 29-30 this year. With plenty of open air tents, live oompah music, ample food vendors, and pretzel eating contests, the Harpoon Octoberfest is tons of fun. Harpoon Brewery is also accessible by the Silver Line, so you don’t need access to a car to join in the festivities.

A bit later in the season, MIT hosts their annual Fall Fest on October 28. Held in beautiful Cambridge and accessible from the Red Line, this fest will have live music, stargazing with MIT astrologers, and yummy fall treats! 
Hopefully today’s blog has helped you get into the fall spirit! If you try any of these fall activities, be sure to tag us on Instagram, or leave a comment below. For more information about Boston living, check out our Boston Tips and Activities page, where you’ll find seasonal recommendations on how to get the most out of the city!

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Olivia is a second-year student in Emerson's Communication Disorders MS program. Originally from Ohio, she is loving Emerson and city life. When she's not writing for the Grad Life blog, she loves to read, bake, and crochet.

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