19 Amazing Things to Do in Boston in October You Can’t Miss 2024

Looking for the best things to do in Boston in October? I’ve got you covered.

I spent a long fun filled weekend exploring Boston at the start of my New England fall road trip, and October is one of the most exciting times to visit. With the fall foliage in full swing and tons of seasonal events happening, there’s no better time to explore Boston.

In this post, I’ll be sharing 19 top things to do in Boston this October. Whether you’re there to see the autumn colors, visit Boston’s historic landmarks, or check out some Halloween festivities, you’ll find plenty of ideas to make the most of your trip.

Alright, let’s jump right in!

Top Things To Do in Boston in October

I could list endless things to do in Boston during October, but let’s stick to 19 of the best.

Boston’s rich history really shines this time of year, with plenty of seasonal activities kicking off in early October. From catching a sports game to apple picking, joining Halloween festivities, or taking spooky tours, there’s something for everyone to enjoy during this spooktacular season.

1. Boston Ghosts and Gravestones Trolley Tour

For some Halloween fun, climb aboard Boston’s “Trolley of the Doomed.” You won’t be doomed, but you may see a ghost or two.

As you cruise through the city’s eerie streets, you’ll hear all about Boston’s most sinister characters—like Albert DeSalvo, aka the Boston Strangler. It’s a night packed with chills, spooky stories, and a whole lot of fun.

2. Go on a Boston Food Tour

The best part about traveling is the food! Don’t you agree?

Well, Boston will not disappoint. You have to go on a food tour when you visit, and make sure you try the lobster rolls and clam chowder.

We took the North End Boston Food Tour. Everything we ate was fantastic, and the neighborhood was really cool to explore.

You’ll learn all about the North End neighborhood, including Little Italy and its culture while tasting some delicious bites.

Pro tip: Come hungry!

3. Take a Walking Tour of the Freedom Trail

The Freedom Trail Walking Tour is a history buff’s dream!

Not only will you learn about the rich history of the US between 1760 and 1775, but for first-timers to Boston, you will see 16 historic landmarks. Some of these include Park Street Church, the Boston Massacre Site, Paul Revere House, the USS Constitution, and the Bunker Hill Monument.

Make sure you pack really comfy walking shoes for this one!

4. Tour Fenway Park

You can’t go to Boston without seeing “American’s Most Beloved Ballpark.”

Even if you are not a sports fan, Fenway Park is iconic. It’s the oldest active ballpark in the MLB and has been home to the Boston Red Sox, since it opened in 1912.

The Green Monster, not a Halloween character, but a high left-field wall, is worth a see.

5. Go on a Bike Tour of The City

For a fun and active way to explore Boston, hop on a bike tour!

You’ll pedal through six different neighborhoods, getting a great mix of the city’s famous sites and lesser-known gems. Along the way, you’ll learn about Boston’s fascinating history and hear all the quirky stories that give the city its charm.

It’s the perfect way to take in Boston while enjoying the crisp fall weather. Plus, you’ll cover way more ground than you would on foot!

6. Do a Pub Crawl

Explore the best of Boston’s hops and history on a classic pub crawl!

You’ll visit some of the city’s top pubs while hearing all about the hidden history behind each spot. Led by a beer expert, you’ll sip cold beers, learn a few fun facts, and have a great time along the way.

It’s a perfect way to experience Boston’s pub culture and enjoy a good drink with a side of history.

Cheers!

7. Harvard Square’s Oktoberfest

This is an Oktoberfest unlike any other!

Harvard Square’s Oktoberfest brings beer gardens, live music, parades, performers, and much more to the party.

Worried about missing the fun? No need! The celebration kicks off right after Labor Day in September and keeps the party going through mid-October.

You’ll be treated to a handclapping, foot-stomping, mind-blowing spectacle you won’t forget. It’s an absolute blast!

While you’re there, take a theatrical and humorous guided tour of the Harvard campus. It’s a gorgeous campus with a lot stories around every corner.

Free Things To Do in Boston in October

Boston has plenty to offer without breaking the bank, especially in October. Whether you’re looking for fall foliage, historic sites, or just soaking up the city’s cool vibes, there’s no shortage of free activities.

Here are some top picks for enjoying Boston this fall without spending a dime!

8. Admire the Fall Foliage in the Boston Common and Public Garden

Don’t even think about leaving your camera behind when you’re touring Boston—especially when you hit up Boston Common! The fall foliage here is next level gorgeous.

It is the oldest public park in America. Established in 1634, and is the perfect place to take a fall stroll through history.

Right next to Boston Common, you’ll find the beautiful Boston Public Garden, the first botanical garden in the U.S. Take a walk along its paths, lined with statues, fountains, and vibrant fall colors.

It’s the perfect spot to spend a free afternoon in the heart of the city.

9. Wander the Cobblestone Streets of Beacon Hill

Beacon Hill must be on your Boston itinerary!

With charming red-brick row houses, gas lanterns, and cobblestone streets, it looks like you stepped into a Thomas Kinkade painting.

And, for all you history buffs—Beacon Hill is dripping with it. You’ll be walking through some of the most iconic spots in Boston, like:

• Massachusetts State House – That shiny gold dome is hard to miss.
• Boston Athenaeum – A book lover’s paradise!
• Old Granary Burying Ground – Resting place of famous patriots.
• Acorn Street – One of the most photographed streets in the country, and for good reason.
• Sunflower House – Bright and cheerful, just like it sounds.
• Prescott House – A beautifully preserved mansion with a serious history.

10. Visit the USS Constitution War Ship

Take a step back in time with a visit to the USS Constitution, the world’s oldest commissioned warship still afloat.

You can enjoy free tours of the ship and museum, making it one of the best ways to save money while having fun in Boston.

It’s a great opportunity to learn about American naval history and explore one of the city’s most iconic landmarks without spending a dime. It’s a really fun and unique activity to do in the fall.

11. Walk Along The Esplanade

Take in the beauty of fall while walking along the Charles River Esplanade.

This 8-mile riverfront path is perfect for a leisurely stroll with stunning views of the fall foliage reflecting off the water.

The Esplanade also hosts special events and live music festivals throughout October, so you might just catch some live tunes as you explore.

It’s a great spot to enjoy the crisp air while soaking up Boston’s seasonal charm.

12. Visit the Boston massacre site

It might not look like much at first—just a simple plaque set into the pavement at the intersection of Congress and State Streets. But don’t let that fool you.

This spot marks a pivotal moment in both Boston and American history.

It’s where the events of 1770 unfolded, sparking tensions that led to the American Revolutionary War.

Standing here will make you reflect on the path to freedom and how a seemingly small moment can change the course of history.

Other Fun Things to Do in Boston in October

Got a solid list of things to do in Boston in October? Well, there’s even more! Boston is full of great activities this time of year.

Let’s check out a few more fun options!

13. New England Aquarium

While this aquarium is pretty small compared to other aquariums, the New England Aquarium is unique and fun.

The centerpiece of the attraction is the Giant Ocean Tank! This four-story tank holds 200,000 gallons of salt water and is home to sharks and penguins to small crabs.

You might even get up close and personal with Myrtle the Turtle – a long-time resident. What a great way to spend a fall afternoon.

14. Shop at Boston Public Market

I’m obsessed with markets when I travel, especially food markets, and Faneuil Hall and Quincy Market totally hit the spot!

Located on Hanover Street, this indoor, year-round marketplace has over 30 artisans all under one roof.

You will find just about anything here from fresh groceries, delicious, prepared meals, handmade crafts, and unique specialty items.

Don’t leave Boston without stopping by.

15. Go on a Whale Watching Tour

Looking for something a little different? A whale-watching tour from Boston is a must.

October is still a great time to catch a glimpse of these incredible creatures as they migrate. Head out on a boat tour and see humpbacks, finbacks, and even dolphins in their natural habitat.

While there are no guarantees, I highly recommend the Boston Whale Watching Catamaran Cruise. This whale-watching tour and its crew are knowledgeable and fun, and the high-speed catamaran gets you to the whales in no time.

It’s a unique experience that gives you a different perspective of Boston—this time, from the water!

Pro tip: dress in layers for the cold wind, and aim for a seat up top or at the front for the best views.

16. Go Apple Picking

Time to throw on those cozy sweaters—it’s apple-picking season!

Luckily, all the best orchards are less than an hour’s drive from Boston, making it an easy fall excursion.

Honestly, I think the best part of New England in the fall is the fresh, hot cider and those warm, sugary cider doughnuts. Plus, it’s really fun to wander through an orchard, picking your own apples.

If you’re ready for some apple-picking fun, here are five great spots near Boston:

• Brooksby Farm – A classic apple-picking spot, perfect for families.
• Boston Hill Farm – Beautiful orchard vibes, and the farm stand is worth a stop.
• Cider Hill Farm – Apples and fresh cider doughnuts? Yes, please.
• Belkin Family Lookout Farm – Apple picking plus hard cider—what’s not to love?
• Smolak Farm – Cozy orchard with great apple varieties and a cute farmstand.

17. Visit The Isabella Stewart Gardner Museum

I’m not much into touring art museums, but this one piqued my curiosity.

The Isabella Steward Gardner Museum is a total gem. You’ll want to check it out.

The museum is housed in a stunning 20th-century Venetian-style mansion. It’s not just about the art. The building itself is a must-see.

You may be asking, who’s Isabella Stewart Gardner?

She was a visionary. Her story is as unique as the museum itself. Seriously, look her up on Wikipedia and prepare to be inspired!

Best Day Trips From Boston in the Fall

So, you’re in Boston and loving it, but did you know you’re just a hop, skip, and a jump away from some of New England’s other must-see spots? If you’re this close, taking a day trip is totally worth your while.

Boston’s prime location makes it easy to escape the city for a day and explore scenic drives, charming towns, and stunning fall foliage.

Let’s check out some of the best day trips you can take from Boston this season!

18. Visit Nearby Salem

If you are looking for the ultimate Halloween spot, Salem is it!

Just 24 miles from Boston, this town goes all out with a whole month of spooky fun. Salem is where you can totally get your freak on.

Halloween is not just a day here. It’s celebrated for the whole month! I’m talking witch lore, creepy legends, a trip to the famous Salem Witch Museum, and a deep dive into that dark chapter in history regarding the Salem witch trials.

And if you’re up for a bigger adventure, consider extending your trip with a scenic Boston to Bar Harbor road trip. It’s a stunning drive through New England’s best fall foliage, with plenty of coastal charm along the way.

19. New Hampshire Fall Foliage Day Tour

If you want to see some seriously jaw-dropping fall colors, a New Hampshire fall foliage day tour is the way to go.

It’s super easy—you’ll get picked up right from your hotel in Boston and whisked away to the breathtaking White Mountains.

The vibrant fall colors against the mountain backdrop are something you have to see to believe. Trust me, this day trip is worth every second, and you won’t find views like this anywhere else!

Is October a Good Time to Visit Boston?

October is an incredible time to visit Boston, especially if you’re a fan of fall. The crisp autumn air, the vibrant fall foliage, and the festive atmosphere make it a perfect time to explore Boston. Whether you’re strolling through historic neighborhoods or enjoying the parks, the city’s fall colors are in full swing—especially in early October.

It’s also the ideal time to celebrate Halloween in a city known for its spooky history. From haunted tours to pumpkin festivals, there are plenty of seasonal events to enjoy. Visiting Boston in October gives you the best of both worlds—beautiful fall scenery and all the fun that comes with the Halloween season.

What’s Boston’s Weather Like in October?

Boston in October brings cooler, crisp weather. Temperatures typically range from the mid-50s to the low 70s during the day, with cooler evenings, so it’s a good idea to wear layers.

While October is generally pleasant, you should also be prepared for some rain, as fall can be unpredictable.

Compared to other times of the year, Boston in October is one of the best months to visit. The summer heat and humidity are gone, and the fall foliage is at its peak, making it a beautiful time for a visit.

Where to Stay in Boston

When deciding where to stay in Boston, I recommend staying in a central location like downtown so you can easily walk to all the major attractions.

We stayed at the Club Quarters Hotel during our visit, and it was the perfect spot. The location was ideal, with everything we wanted to see within walking distance. Plus, we really enjoyed the pub downstairs—it was the perfect starting point for our self-guided pub crawl, complete with live music!

I’ve included my top hotel picks in Boston below:

Tips For Visiting Boston in October

Visiting Boston in October is one of the best times to experience the city, with beautiful fall foliage and cooler weather. But before you go, there are a few things to keep in mind to make the most of your trip.

Here are some helpful tips for visiting Boston in October!

Get a Boston City Pass

If you want to see all the best of Boston and save money, grabbing a Boston CityPASS is the way to go.

It gets you free admission to some of the city’s top attractions, like the New England Aquarium and the Museum of Science.

You’ll be able to explore the entire city without paying full price, which makes it a super easy way to get the most out of your trip without overspending.

Don’t Drive in Boston!

Don’t drive in Boston—seriously, it’s not worth the hassle. The road network is a confusing maze of one-way streets, and parking is both limited and expensive.

Renting a car will not only cost you a pretty penny, but you’ll likely end up frustrated trying to navigate the city.

Boston is super walkable, and with great public transportation like the “T,” there’s no need to bother with a rental car. Save yourself the stress and stick to walking or taking public transit!

Don’t Take a Taxi Either!

Also, don’t bother taking a taxi or Uber in Boston—it takes way too long to get anywhere, and you’ll likely end up sitting in traffic. Plus, Boston drivers are a breed of their own, so the ride might be more stressful than it’s worth.

With the city being so walkable and Boston’s subway system so efficient, it’s much easier and faster to get around on foot or by taking the T.

Save yourself the frustration and skip the cabs!

Iffy Weather

Boston’s fall weather can be pretty unpredictable, so you’ll want to pack for all kinds of conditions. One minute, it could be sunny and warm, and the next, a chilly breeze or rain might roll in since you are right on the coast.

It’s smart to bring layers, especially a rain jacket. You never know what you’re going to get with Boston’s iffy weather, so come prepared for anything!

FAQ’s About Visiting Boston

Here are some quick answers to common questions about visiting Boston, especially during the fall season.

Is Boston Expensive to Visit in October?

Yes, Boston can be more expensive in October due to the popularity of fall travel and the foliage season, so plan ahead to get the best deals.

What should I pack for Boston in October?

Pack layers, as the weather can be unpredictable. Bring a warm jacket, comfy shoes, and a raincoat just in case.

When can you see fall colors in Boston?

Predicting when the fall foliage is going to peak is nearly impossible. Usually, the fall colors peak in mid to late October, but you’ll start seeing foliage changes as early as the beginning of the month.

Where is the best fall foliage in Boston?

Some of the best spots for fall foliage in Boston are the Boston Common, the Public Garden, and the tree-lined streets of Beacon Hill.

PIN FOR LATER!

That’s a Wrap on Things to do in Boston in October

So, now that you’ve got the scoop on the top things to do in Boston in October, it’s time to grab your coziest sweater and start planning. Between the fall foliage, Halloween fun, and everything in between, Boston in the fall is pure magic.

Whether you’re here for the history, the fall leaves, or just some good old New England charm, you won’t be disappointed.

Enjoy your fall adventures.

Catch you later!