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12+ BEST Things to Do in Boston in the Fall

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From whale watching cruises to catching the colors of the famous New England foliage, these are the best things to do in Boston in the fall!

boston in the fall

Ah, Boston. There’s nowhere else like it. 

It’s one of those places that’s perfect to visit no matter what time of year it is. Summers are bright and beautiful, winters are magical and covered in thick white snow.

This is controversial, but I don’t think any of the other seasons beats Boston in the fall. Sure, most cities come alive with a bit of autumnal charm, but something about Boston just hits different.

I mean, think about it: there’s the famous fall foliage, apple picking, and Massachusetts is one of the best US states to celebrate Halloween. After all, the spooky city of Salem is only 45 minutes away.

best things to do in boston in the fall
Boston is a city that comes alive in the fall

Maybe you’re already planning an autumn excursion to Boston. Perhaps this city has long been on your bucket list and you’re trying to figure out the best time of year to go.

Or maybe, you’re not set on one location yet – though I reckon this blog might sway you. That’s because I’m about to show you the very best fall activities in Boston!

Planning your next holiday to the States? Then check out my winter guides on Baltimore, Detroit and Washington DC for a touch of snow, or my summer guides to Houston, Lake Tahoe and Park City.

boston travel
Boston has such a time-worn charm about the place

Weather in Boston in fall

The weather in Boston changes over the course of the fall months, getting progressively colder.

By October, you’re looking at highs of 17°C (62.6°F) and lows of 8°C (46.4°F). By the time November comes along, you can expect highs of 11°C and lows of 3°C (37.4°F). It really does get cold here during fall and winter, so make sure you wear lots of layers and wrap up warm!

The Best Things to do in Boston in Fall

See the famous Fall Foliage

When it comes to Boston in the autumn, nothing springs to mind quite as quickly as its famous fall foliage.

boston fall foliage
The fall foliage draws in people for all over

The city comes alive in gold and crimson and bronze as the colour of the leaves shift for the season. It’s pretty special, and people come from all over to see it. Seriously, there’s a name for them and everything – “leaf peepers”. 

Fall Foliage can be seen all over the city, but some of the best locations to check out are along the Charles River, Public Garden, Beacon Hill and the Esplanade. 

Go whale watching

Whale watching is one of the best activities Massachusetts has to offer. Luckily for us, September and October are two of the best months for it. 

boston things to do
September and October are the two best months for whale watching

Because it’s one of the most popular fall activities in Boston, there are tons of cruises that’ll take you off the coast and into these creatures’ natural habitat. 

I personally recommend this tour. Accompanied by experts from Whale Center of New England, you’ll learn all about these marine animals, and be taken to prime spotting locations. You’ll have the chance to see humpback whales, finback whales and minke whales, as well as white-sided dolphins.

Visit the historic city of Salem

Salem – site of the infamous 1692 Salem Witch Trials – is just 45 minutes away from Boston. This is a city that’s proud of its strange, haunted heritage, and that’s why it’s one of the best places in the US to visit at Halloween.

things to do near boston
Salem is one of the best places to visit near Boston

In fact, the classic movie Hocus Pocus is set in Salem, and many parts of it were filmed there. If you’re interested, you can find some of the Hocus Pocus filming locations here.

It’s shown every year during Haunted Happenings, a series of spooky, Halloween events throughout the city. There’s tours, haunted houses, seances, fairs and much more throughout October. 

Visiting outside of October? There’s still plenty to do. Take a Haunted Walking Tour or visit the Salem Witch Museum.

Enjoy Halloween fun at a pumpkin patch

Speaking of Halloween, pumpkin patch picking is an absolute must if you’re heading to Boston in the fall, specifically October.

pumpkin picking
It’s not fall without going pumpkin picking

It’s not just about finding the perfect pumpkin, it’s about enjoying all of the spooky magic the States has to offer this time of year.

Loads of them have live music, hot cider, apple bobbing, corn mazes, even fairground rides if you’re bringing kids along. There’s tons of choice, too: Boston Hill Farm, Smolak Farms, Pakeen Farm and many more in and around the city.

Or try apple picking

Pumpkin picking not your bag? Go for apples instead. This is one of my favourite fall activities in Boston, and an absolute New England classic.

apple picking
Apple picking is a great alternative to pumpkin picking

It’ll usually take you out of the city too, giving you a chance to escape the hustle and bustle and see some of the surrounding Massachusetts scenery.

Try Belkin Lookout Farm, Carver Hill Orchard, or Honey Pot Hill Orchards to name a few. As well as picking apples, make a day of it – sip hot cider and visit the farm animals.

Experience one of Boston’s local hikes

There’s plenty to love about Boston in the fall. But for me, one of the absolute best things about it is the scenery. And one of the best ways to take all of that in is through exploring the local hikes.

boston autumn
There are some great hiking trails near to Boston

In the city itself, you’re more likely to find gentler paced walking trails: the Freedom Trail or the Emerald Necklace.

Head outside of Boston for the more serious trails, like the Middlesex Fells Reservation or the Blue Hills Reservation, both of which can be reached by public transport. If you’ve got access to a car and want to make a day of it, Boston is a great base to explore New Hampshire’s White Mountains.

Spend a day at a museum

Boston’s a city of heritage like any other. Spend a day getting a bit of education by exploring the local museums.

museum of science boston
The Museum of Science is a great place to visit

You’ve got a good few to choose from. Nurture the left side of your brain at the Museum of Science, view some incredible exhibitions and works of art at the Museum of Fine Arts, or embrace the political at the JFK Presidential Library and Museum.

Cruise through Boston’s harbours

Want to see Boston’s historical sights in style? Jump on a cruise around Boston’s inner and outer harbours.

what to do in boston
A Boston boat tour is one of the best things to do in the city

Take in views of the USS Constitution, Old North Church, and the Bunker Hill Monument, against the panoramic backdrop of the Boston Skyline. 

You’ll get a healthy dose of American history, but tons of beauty too – this tour will take you through the Harbour Islands National Park.

Rent a bike for the day

Explore the best of Boston’s sights on two wheels. Renting a bike in Boston in the fall is super easy – just head on over to Blue Bikes or Boston Bike Rentals.

blue bikes usa
It’s really easy getting around Boston by bike

If you don’t feel comfortable cycling through the streets, head to one of Boston’s many parks or green spaces, like the Public Garden or Boston Common. Rent the bike for the whole day and traverse the best of Boston’s Fall Foliage.

Take a Ghosts and Gravestones tour

If you loved the spooky sights of Salem, why not take your “frightseeing” one step further? If that’s what you’re into, the Ghosts and Gravestones Tour is an absolute must. Especially if you’re timing your visit with Halloween.

ghost and gravetones tour
This is the perfect tour around Halloween

This tour takes you back in time and through Boston’s grisliest history. Gruesome murders, paranormal hijinks, and the legend of the Boston Strangler, this tour has it all. 

Watch the Head of the Charles Regatta

If you find yourself in Boston on the third weekend of October, don’t miss Boston’s biggest boat race: the Head of the Charles Regatta. 

head of the charles regatta
The Head of the Charles Regatta is an amazing event to watch

This is three days of races that draw in audiences from all around the world, and promise beautiful foliage views and festivities alongside the excitement of the regatta itself.

Explore the Freedom Trail

freedom trail boston
You’re bound to walk the Freedom Trail while in the city

Get up close and personal with Boston’s history and heritage by exploring the Freedom Trail.

The Freedom Trail is a series of tours and historical sites around Boston: unique museums, churches, burial grounds, and other historic markers that tell the tale of the American Revolution.

Where to Stay in Boston in the Fall

Boston Harbor Hotel

boston harbour hotel

A 5-star waterfront hotel overlooking Boston Harbour, the award-winning Boston Harbor Hotel is perfect for those with cash to splash. It’s got everything you need – restaurants, a gym, and an incredible view of the water.

You could enjoy your stay without ever even stepping outside, but exploring has never been easier. You’re in the heart of the city, after all.

Staypineapple, A Delightful Hotel

where to stay in boston

When it comes to Staypineapple, A Delightful Hotel, the clue’s in the name. Located in Boston’s historic South End, Staypineapple is a European-style boutique hotel with tons to offer.

It’s not just about marble bathrooms and plush rooms though – this hotel is a stone’s throw from some of Boston’s best attractions, 

HI Boston Hostel

boston hostel

Can Boston be done on a budget? You bet it can. HI Boston Hotel is in the heart of the city centre, within walking distance of Boston Common, one of the best sights to see the famous foliage.

The hostel has dormitory-style rooms with options for mixed, male or female accommodation, as well as private rooms for an extra cost. As well as a shared kitchen, guests have a game room and a bike storage space.

Now that you know the best fall activities in Boston, it’s time to get planning your trip. Are you heading to the states this autumn? Tell me all about your plans in the comments.

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12+ BEST Things to do in Boston in the Fall

About the Author

  • Georgie Cunningham

    Georgie Cunningham is a freelance content writer and strategist based in Bristol. When she’s not writing (or thinking about) content, she’s writing fiction, travelling, or chasing after her crazy cocker spaniel, Cosmo.

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1 thought on “12+ BEST Things to Do in Boston in the Fall”

  1. I would like more information concerning the immediate surrounding area of Boston as well as hotels in Boston. We plan a three day visit with approximately 50 people.


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