13 Best Things to Do in Boston in the Fall

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Fall is the perfect time to visit Boston! The city comes alive with color and there are so plenty of great things to do.

If you’re looking for a guide to help you plan your trip, look no further. I’ve got you covered with a list of my favorite things to do in the city.

From warm apple cider & donuts to haunted ghost tours, there’s something for everyone! Keep reading for my local guide to enjoying Boston in the Fall.

Watch the Head of the Charles Regatta

Every October, rowers from around the globe gather for the largest rowing competition in the world, The Head of the Charles Regatta.

Over 3 days, rowers compete in a 3-mile race down the Charles River in a variety of groups, ranging from youth to adults. 

The event also draws a super preppy, New England-y crowd, which makes for some interesting people watching on top of cheering on the competitors.

In 2022, the Head of the Charles Regatta takes place October 21-23.

Cheer on a local football game

It’s no secret that Boston is obsessed with its local sports teams!

Get in on the fun by cheering on our NFL team, the New England Patriots, or one of our college teams, the Boston College Eagles.

The New England Patriots play at Gillette Stadium in Foxboro, MA, about 45 minutes outside of the city.

While you can take the commuter rail there, it’s easier to get to and from Foxboro via car.

The BC Eagles play at Alumni Stadium in Chestnut Hill, MA, right on the city border, so it’s quite easy to get to a game via public transportation.

Whichever team you choose, you’re guaranteed to have a great time cheering them on.

Get apple-y snacks at Red Apple Farm in Boston Public Market

If you can’t make it out of the city for apple picking, head down to the Boston Public Market next to Haymarket T station.

Inside the main entrance of the market is Red Apple Farm, a vendor stand for a local Apple farm!

Red Apple Farm sells apples, jam, cider donuts, hot cider, and other homemade goodies. 

While you won’t have the fun of picking your own apples, you won’t have to fight the suburban traffic and can pick up other Fall goodies from other local vendors in the market.

Have a picnic in the park

Before Winter rolls in and makes a slushy, grey mess, enjoy a picnic at the Boston Public Garden, the first botanical garden in the US, or Boston Common, the oldest city park in the US. 

Better yet, head to Boston Public Market for apple cider donuts and other food first!

Do a Ghosts & Gravestones tour

NOTE: This tour is recommended for ages 13 & up only. Kids under 6 are not allowed. 

If Halloween is your jam or you love spooky stories, definitely check out the Ghosts & Gravestones tour.

The tour provides a unique look at the spooky and haunted side of the city, both past and present. 

Everything takes place aboard a trolley, with tour guides getting into the spirit with scary costumes.

Tours start at 6 PM daily and run for about 1 hour and 30 minutes.

Do a brewery tour

One of my favorite things to do in Boston in the Fall is to take a brewery tour or hit up a beer garden for a pumpkin ale or hard cider.

Harpoon Brewery and Sam Adams Brewery are my top pick for brewery tours in the city. 

Both breweries host events in the Fall, such as Harpoon Oktoberfest, and have taprooms if you want to just do a beer tasting rather than a tour.

If you prefer a guided tour or want to see more than 1 or 2 breweries, check out this guided brewery tour, featuring SIX breweries!

As always – if you drink, please drink responsibly!

Visit old cemeteries

Another interesting Halloween activity in the city is to visit the Granary Burying Ground and King’s Chapel Burying Ground, both located on Tremont Street near the Downtown Crossing area.

King’s Chapel Burying Ground was established in 1630 and is the oldest cemetery in Boston. 

Unless you know early American history well, you might not recognize most of the names of people buried here. 

But, it is still an interesting cemetery to visit, especially amidst all of the modern buildings around it. 

About 1 block down across the street is the Granary Burying Ground, which was established in 1660. It is the 3rd-oldest cemetery in the city.

The Granary Burying Ground is the resting place of many well-known American historical figures, such as Paul Revere and 3 signers of the Declaration of Independence (Samuel Adams, John Hancock, and Robert Treat Paine).

Visit the iconic Acorn Street in Beacon Hill

One of the most instagrammable spots in Boston is the iconic Acorn Street in Beacon Hill.

On Acorn Street, brick rowhouses line a short, hidden street made of cobblestone.

It’s like a scene from history, plus all the deep reds and colorful trees make for a perfect Autumn photo. 

NOTE: Acorn Street is a residential neighborhood, so please don’t make noise, sit on people’s stoops, or clog up the street and cause traffic while you’re there. 

Take a tour of Harvard Yard

The Fall season means college students have arrived to attend one of many higher education institutions in the Boston area, such as Harvard University.

Whether you’re thinking of attending Harvard in the future or just want to see their stunning campus, Fall is the perfect time for an (unofficial) Harvard University tour. 

You’ll learn about Harvard’s history, see its gorgeous buildings, witness student life happening around you, and get a peak of Fall foliage on campus.

Go for a hike at Middlesex Falls Reservation

I don’t know about you, but after a long, hot summer, I’m ready for some pumpkin-spiced goodness and a scenery that can give Instagram filters a run for their money.

I’m about to let you in on a little secret – the Middlesex Fells Reservation is the place to be in the Fall.

The glowing foliage and crisp autumn air make this spot a top contender for your weekend plans.

Located just north of Boston, this park is filled with tons of biking and hiking trails, as well as a dog park.

So round up your squad, grab your flannel and boots, and go soak up the Fall vibes at the Middlesex Fells Reservation.

Explore the Boston Harbor Islands

The Boston Harbor Islands are one of the city’s most underrated things to do. But who wants to visit them during the sweltering summer months with tons of overexcited tourists?

Not you, savvy adventurer. Nope, it’s time for Fall season. Trust me, visiting at the tail end of the season is the best time to go.

The air gets a little crisp and the changing fall foliage will undoubtedly take your breath away. Plus, the crowds thin out and the ferries that shuttle you to-and-fro are less crowded.

Get lost in the serenity of nature, enjoy fantastic hikes, and of course, savor the sweeping views of the city skyline in the distance.

Just be sure to plan your visit for early fall, as the ferry only runs until early October. Check the Boston Harbor Islands website for more details on ferry dates and schedule.

See the Fall foliage at Arnold Arboretum

Go leaf peeping without even leaving the city at Arnold Arboretum. 

Located in the Jamaica Plain neighborhood, the Arnold Arboretum boasts 281 acres of gorgeous grounds with over 15,000 trees and plants.

The best part? The Arnold Arboretum is FREE!

Take a day trip to Salem, MA

For the ultimate Fall bucket list adventure, head to Salem, MA for a Halloween-filled day trip.

I might be a bit biased since I’m a local, but Salem has the best Halloween celebration in the US.

Visiting Salem, MA in the Fall is definitely something to experience at least once!

For tips on planning your day trip to Salem, check out my Salem, MA Halloween guide, best tours in Salem post, and things to do in Salem guide.

Will you visit Boston in the Fall?

I hope you found my guide to be helpful for planning your visit.

For more tips on what to do, visit my guide on activities in Boston year-round, check out Bostons’s best food festivals or general festivals and events in Boston, learn more about the rest of New England in the Fall, or find other places to visit in the Fall in the United States.

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About the author

Meg Frost is a Boston-based travel blogger that helps people embrace technology to make vacation planning and traveling wicked easy, affordable, and fun.

She holds an M.A. in Journalism from Northeastern University and B.S. in Communication & American Studies from University of Miami.

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This post was originally published August 8, 2021. It was last updated August 17, 2023.