Even though it’s New England’s largest city, there’s no shortage of fall coziness to be had in Boston! Offering the best of both worlds when it comes to big city amenities, and quaint neighborhoods, Boston is one of the best places to enjoy the autumn season.
This post shares all my favorite things to do in Boston in the fall season, including where to find the best foliage displays, spooky Halloween activities, best festivals and parties, and even the best fall day trips from Boston. With that, let’s get started!
Is Fall A Good Time To Visit Boston?
Oh, absolutely! There’s just something extra magical about Boston in the fall season, and the city does an absolutely fantastic job capturing all the best things about this time of the year. You’ll find curated seasonal menus at the restaurants that highlight autumnal flavors, crunchy leaves on the sidewalks, parks filled with fall color, and so many things to do to fill up your itinerary.
On top of that, the fall season offers very comfortable weather. In the summer, Boston is hot. But once October hits, temperatures begin to drop, and while there can be the odd hot day, the weather is generally cooler and more pleasant for exploring the city. And since Boston is a great city to explore by foot, this just adds to the appeal of a fall visit.
Best Time To Visit Boston For Fall Foliage?
Mid-October is a great time to visit Boston for peak fall foliage, but honestly, the entire month of October will be beautiful. Early October will bring the first few peeks of the leaves changing, and by the third week of the month, the city is usually about as colorful as it gets. The color will typically last through Halloween, too.
But even after Halloween, you’ll usually find some colorful foliage still hanging onto the trees, and lots of it sprinkled all over the sidewalks.
However, one thing to know about fall foliage anywhere in New England, is that colors can peak at different times from year to year. The changing leaves is impacted by temperature and weather patterns throughout the entire year, so it doesn’t always happen at the same time. However, for Boston, mid-October is almost always a safe bet for the best fall color.
Where To See Fall Foliage In Boston
Let’s kick off my list on celebrating fall in Boston with where to find the best foliage around the city! Now, there are definitely more than these 3 places to see fall color, but I wanted to showcase the best of the best when it comes to colorful leaves. So these are the places you’ll want to visit on your autumn trip to Boston for foliage:
1. The Public Gardens
If there’s one place to see fall foliage in Boston, it’s the Public Gardens. You’ll be able to enjoy colorful trees backdropped by the city skyline, take perfect fall photos on the pedestrian bridge, and see foliage at pretty much every turn in the park.
The Public Gardens are gorgeous year-round, too, so while they’re even more special in the fall, this is just a place that should be on anyone’s itinerary if you’ve never been.
Pro Tip: Many people hope to take a ride on the famous Swan Boats in the park, and while this is a really fun thing to do, they’re only open in the summer. They typically shut down right after Labor Day, so this isn’t something you should plan on doing during your fall trip. However, definitely plan to enjoy the rest of the park during this beautiful season!
2. Boston Common
Right next to the Public Gardens is Boston Common, which is another wonderful park in the city that’s a great spot to enjoy fall foliage colors. While The Common isn’t quite as picturesque as the Public Gardens, you’ll find walkways and lawns at this park filled with fall color.
And since it’s just steps from the Public Gardens, it’s so easy to see them both at the same time.
3. The Esplanade
One of my favorite walks in Boston year-round is the Esplanade, and it’s definitely the best in the fall season. A paved walkway along the Charles River, the Esplanade is packed with foliage color in the fall, and is such a lovely place to enjoy a crisp, autumn walk.
Stretching over 3 miles, you can really walk for a while here, too, and there are fun places to stop along the way. If you don’t want to walk the whole thing, it’s easy to exit and head back into the city when you’re ready. And if you’re looking for things to do along the path, I recommend visiting the floating dock, and admiring the street art (there are both permanent and seasonal displays to check out!).
Spooky Tours To Take In Boston In The Fall
While most of these tours are offered year-round in Boston, a spooky tour is always better in the fall, right? With Halloween approaching, fall decorations everywhere, and the cool night air, all of these things combined just beg you to book a fun haunted tours in one of the country’s most haunted cities!
4. Ghosts & Gravestones Trolley Tour
The Ghosts & Gravestones Trolley Tour is one of the most popular in the entire city, and for good reason! You’ll hop aboard a trolley at night to cruise around Boston with a costumed guide, and learn all about the spookiest hauntings around the city.
Sites you’ll see along the tour include the Boston Tea Party, the historic North End, and you’ll even get off the trolley to walk through the city’s oldest burial grounds for all the goosebumps and chills you could want.
5. Haunted Pub Walking Tour
The Haunted Pub Tour is perfect for those looking for a good mix of fun, history and a few scares. This walking tour takes you to some of the city’s most haunted pubs, where your expert guide will share spooky stories of ghost sightings. During each pub visit, you’re also welcome to purchase a drink to enjoy while learning about the haunted happenings.
This tour also passes by Beacon Hill, King’s Chapel, and Granary Burying Ground for all the spooky stories you could possibly want between your visits to the pubs.
6. Death & Dying Walking Tour
The Death & Dying Tour is perfect for those looking for an eerie walking tour through the city that tells the tales of the most haunted places in Boston. This tour is so spooky, that it’s an adult-only event that takes place at nighttime.
Fun Things To Do In Boston In The Fall
For more fun things to do in Boston in the fall season to celebrate everything that this season is about, check out some of these recommendations below:
7. Sip On Seasonal Brews
Boston is such a great city for crafts breweries, and in the fall, you can take advantage of all the fun seasonal flavors that are special releases.
My favorite brewery to visit in Boston is Trillium Brewing, and in the fall, their Barrel Aged Spice Cake Imperial Stout is to die for. They often have fun cocktail creations in the fall season, too. Trillium also has a few Beer Garden locations around the city, including the Greenway, Fenway and the Common. Check out one, or all of them – I won’t judge 😉
Another popular place for local beer in Boston is Harpoon Brewery, and their Flannel Friday is the one you’ll want to order in the fall.
8. Order Some Seasonal Cocktails, Too!
In addition to seasonal craft brews, you’ll also want to check out all the awesome seasonal cocktails that are poured around the city! Infusing drinks with apple, maple, and ginger, this is a great way to savor the flavors of the season before heading out to dinner.
A great place to check out is the Boston Harbor Distillery, which has a really fun cocktail bar that serves up creative drinks with seasonal specials. While here, you can also book a tour of the distillery and get a behind-the-scenes look at how their liquors are made.
Later in the post, I recommend staying at the Boston Harbor Hotel, and if you happen to book a room there, you won’t have to stray far for a great cocktail! The Rowes Wharf Bar does an awesome job with fall-inspired drinks that incorporate the flavors of the season.
Other great places for cocktails in Boston are Next Door Speakeasy, Hecate, and Birds of Paradise.
9. Enjoy The Last Whale Watch Tours For The Year
The fall season brings the last of whale watching in the New England region, and you can actually head out on a whale watch tour right from Boston! Whales have usually migrated too far south once October is over, so if one of your goals was to spot some whales this year, book your tour before Halloween!
Whale Watch tours from Boston visit the word-famous Stellwagen Bank Marine Sanctuary, which is where the tours from Provincetown on Cape Cod go – so you’re definitely going to the best place in New England on these tours.
Tours in Boston typically depart from Long Wharf along the waterfront area, and last for about 3.5-4 hours. And since it’s the fall season, you’ll want to be sure to bundle up, as the air will be much colder out on the water. I’d recommend packing a beanie, a warm coat, and even some gloves to stay warm.
10. Try ALL The Chowders
I love a good cup of New England clam chowder year-round, but man, is it even better in the fall and winter! The chilly air makes you appreciate a warm, creamy cup of chowder even more, so whether it’s your first-ever cup of chowder in the area, or you’re a seasoned pro, it’s one of the best things to have in Boston in the fall.
One of my favorite places for both seafood and chowder in Boston is the famous Union Oyster House. This is a popular place that some may call touristy, but honestly, I think it lives up to its reputation. First-time visitors will love the vibe here, as well as the selection of wonderful, fresh seafood. And this is a place where you don’t want to skip the clam chowder!
Walrus & Carpenter Oyster Bar, Neptune Oyster, and Atlantic Fish Company all also have incredible cups of chowder!
🍁 Want to try the best of Boston’s food? I recommend booking a food tour!
Click here to check out my round-up of the best Boston food tours!
11. Get Cozy At Beacon Hill Books & Café
What is it about fall and wanting to throw on a blazer, sharpen pencils, and crack open a good book in the fall season? If those vibes are up your alley, you’ll want to add a trip to Beacon Hill Books & Café to your itinerary.
A new addition to Boston, this bookshop is equal parts cozy and Instagram-worthy. It just so happens to also be a place you’ll probably never want to leave if you love books and a warm drink on a fall day.
The entire store is designed to make you feel like you’re browsing someone’s personal library in their historic home, but the selection is absolutely never-ending. You’re pretty much guaranteed to find your next great read during your visit.
The on-site café is about as picturesque as it gets, and serves breakfast, lunch and lite bites for dinner, as well as an afternoon tea on Sundays.
Since opening, this place has gotten rather popular, so I recommend booking a table online in advance to ensure you can snatch up a table. I suggest arriving an hour early so you can pick out a new book to start reading, purchase it before your reservation, and then spend a cozy afternoon in the café with delicious food and a great, new book.
12. Take A Crisp Fall Walk In Beacon Hill
Great news! Beacon Hill Books is located in probably the cutest and coziest neighborhood in Boston, so before or after your visit to the bookstore, budget some time to explore the cobblestone streets of Beacon Hill.
In the fall season especially, this entire neighborhood feels like a New England postcard. You’ll spot fall foliage, historic streets, gorgeous brownstones perfectly decorated with pumpkins on their stoops, and cute little boutiques with lovely fall window displays. This is a great place to just wander, and take in all the fall vibes. Just be sure to have your camera ready at all times – you’ll need it 😉
13. Pick Up Fall Treats At Tatte Bakery
One of the most popular bakeries in Boston is Tatte Bakery & Café, and honestly, it’s worth waiting in line in the fall season for one of their apple pastries! I’m in love with their apple turnovers, which are the perfect fall treat on a crisp day. They also offer up great spiced lattes in the fall season.
Grab one of these to go to snack on while you explore Beacon Hill, or plan to stay a while and have breakfast or lunch at the café. The interior of each location is so stunningly beautiful, so it’s worth it to linger and enjoy the atmosphere.
In the fall season, they have other delicious goodies like homemade maple pecan pie, pastries infused with cinnamon and pumpkin flavors, and savory dishes spiced with cardamom. It doesn’t get much better than that, right?
14. See The Giant Pumpkins At Boston Public Market
The Boston Public Market is a great stop to make year-round, and in the fall season, you’ll want to swing by to check out the giant pumpkins that are on display for your dose of autumnal fun.
But the fun doesn’t stop there at the Market! The second half of October brings some fun events like the Urban Pumpkin Patch, Pumpkinpalooza, Pumpkin Vase Flower Arranging, and a Taste of the Season food event. If any of these sound like they’re perfect for your itinerary, check them out here before visiting!
15. Join A Walking Tour
Boston is one of the most charming and historic cities in the entire country, and an easy way to get to see all the best places if it’s your first time is by joining a walking tour. There are all kinds of wonderful tours to check out in the city that cover everything from history, the Freedom Trail, to food tours (mentioned earlier!).
The fall season is actually my favorite time to take a walking tour because of the more mild weather, so grab your scarf and sneakers, and get out there to see all the amazing historic places around Boston this fall.
Here are some of the best walking tours around Boston:
16. Get Some Seasonal Cupcakes
One of my personal favorite things to do whenever I visit Boston is place an order for whatever seasonal cupcake flavors are available at Georgetown Cupcake, and they never disappoint.
During the month of October, you’ll find special Halloween-themed cupcakes, as well as pumpkin flavors, on their menu. And they make it so easy to see what’s available by going to their “monthly specials” menu on their website. From there, you can place an online order to make sure you get the exact flavors you want, and have them ready for you when you arrive.
Pro Tip: These cupcakes taste way better when you eat them in your hotel bed at the end of the day 😉 Juuuuust sayin’.
17. Enjoy Foliage Views On A Cruise
One of the best ways to enjoy Boston in the fall season is to take in views of the skyline from the harbor, and good news! There are some awesome cruises available to help you plan the perfect day.
My favorite, however, is this sunset cruise, because there’s just something so dreamy about seeing the fall colors enhanced by the amber glow of the setting sun. On board, have your camera ready to snap photos of the skyline during the best time of the day. And drinks and snacks are also available on the boat to make your trip even more fun.
18. Experience The Arts During Doors Open Day
For anyone out there hoping to get their fill of arts and culture on their fall trip to Boston, you’ll want to pay attention to this one. Every October, the Fenway Alliance coordinates a special Doors Open Day, where over 80 cultural experiences can be enjoyed at absolutely no cost.
The event changes from year to year, and has only continued to grow since its inaugural event in 2001. But past events have included dancers, art exhibits, concerts, and so much more.
19. Stroll Around Harvard Campus
Like I mentioned earlier in the post, fall always makes me want to buy a new blazer, throw on some loafers, and feel like a student again … maybe without the classes and homework 😉 If you share the same sentiments, then a tour around the historic Harvard University campus may be something you’ll enjoy!
Having walked around Harvard myself, I can honestly say it’s such a cool thing to do when visiting Boston, especially in the fall season for all those back-to-school vibes.
And while you can definitely just walk around the campus on your own, you can also book a really fun and quick tour that’s led by actual Harvard students. Get the inside scoop on what life is like on campus, find all the prettiest buildings, and listen to entertaining stories from your guides along the way.
Awesome Fall Day Trips From Boston
While there’s so much to do right in Boston proper in the fall season, there are some amazing places nearby that are especially magical in the fall. These are the destinations I recommend if you’re looking to add a day trip or two to your fall Boston itinerary:
20. Salem, Of Course!
If you only have time for one fall day trip from Boston, it’s just got to be Salem, right?! I mean, it’s really the heart of all things Halloween in New England, and through the month of October, it’s one of the most exciting places to be for all things spooky.
During your day trip, you can join a Hocus Pocus filming locations tour or a spooky ghost tour (or both!), visit the Salem Witch Trials Memorial, and participate in all the fun Halloween events that take place all month long during Haunted Happenings.
The best way to visit Salem for a day trip is to take the ferry from Boston. Salem in October is, well … crowded. And parking will be a challenge, for sure. Leaving your car behind is a good idea during this time of the year, and since Salem is pretty small and walkable, you won’t have to worry about getting around on foot.
The ferry also takes less than 1 hour to get to Salem, so by the time you drive out of the city and find parking, it’s probably faster to just take the ferry.
Pro Tip: When you book your tickets, be sure to book both your ride to Salem, and your return trip back to Boston. Prices reflect a one-way ticket only!
21. White Mountains In New Hampshire
A great tour option from Boston, especially for those who plan to use Boston as their home base for their fall trip, is this awesome fall foliage tour through the White Mountains in New Hampshire. Taking all the guess work out of planning your own trip there, this tour does it all for you.
It’s a long day at around 12 hours, but you’re going to see the best of what New Hampshire has to offer in terms of fall foliage in one easy day trip. An expert guide takes you to some of the best spots for foliage in the area, including the famous Kancamagus Highway, North Conway, and the iconic Omni Mount Washington Resort (which is rumored to be haunted!).
One of my personal favorite fall places to visit that’s close to Boston is Newburyport. This little city feels more like a quaint, small town, and has amazing shopping and dining, waterfront scenery, boat tours, and of course … fall foliage. To me, it feels like the set of a Hallmark movie.
Visiting from Boston is pretty easy, too. There’s a commuter train that goes right to Newburyport, and it takes just over an hour to get there. It drops you off about a 30-mins walk from the heart of town in Newburyport, but you could enjoy the walk on a nice fall day, or call a taxi (Ride Share services up this way are hit and miss).
To go at your own pace, I’d recommend renting a car to drive up to Newburyport, though. You can easily spend the day here, but there are some fun stops to make along the way, including Rockport for coastal charm. And you could choose to continue up to Portsmouth, NH for more fall foliage, and a cute town atmosphere.
An amazing place for fall foliage and cozy vibes is Sturbridge, MA, which is just over an hour outside of Boston. Famous for Old Sturbridge Village, which is wonderful year-round, it’s especially stunning in the fall season. This cute little town is also home to some wonderful parks for relaxing nature walks, a nice apple orchard, and Altruist Brewing Company.
Lastly for charming towns near Boston for cozy fall vibes and foliage, you’ll want to check out Concord. Located less than hour outside the city, it’s famous for its American Revolutionary War sites, and of course, Louisa May Alcott’s family home.
While all these things are worth checking out, it’s especially beautiful in the fall season with all the lovely foliage color at every turn. You’ll find historic homes lining the streets and bright red and orange leaves on all the trees. This is a great escape from Boston if you’re looking for small-town charm, history, and postcard-worthy moments.
25. Visit A Haunted House
While there are no haunted houses right inside the city of Boston, there are some really great ones to check out nearby!
One of the most famous haunted attractions in Massachusetts is the Lizzy Borden House in Fall River, which is about an hour outside of Boston. Ghost tours are given inside the original home, and you can even book an overnight stay if you’re looking for the ultimate thrill.
There are several other haunted houses and attractions nearby – I have an entire post on these to help you pick the best one for you, so be sure to click on that link below (at the end of this section).
26. Experience The Davis Mega Maze
Located in Sterling, which is just about an hour outside of Boston, you’ll find the very fun Davis Mega Maze. This corn maze spans over 3 miles and 8 acres, and can take anywhere from 30 minutes to 3 hours to finish, according to their website! So, you can really make an entire day out of it.
During the month of October, they really make their farm a fun destination, too, and you’ll find live music, craft beer and drink vendors, awesome food vendors, zip lines, camp fires, and special Halloween events. If you’re looking to plan the ultimate fall day of fun from Boston, this is the place to go.
Here are some posts to help you plan your fall day trips from Boston:
- The Ultimate Salem, MA Day Trip Guide
- Best Haunted Houses & Places To Check Out In Massachusetts
- Best Things To Do In Newburyport, MA
Fall Festivals & Events In Boston
27. Titanic Masquerade Halloween Yacht Party
For the ultimate Halloween party on the water, you’ll want to snatch up your tickets to the Titanic Masquerade Halloween Yacht Party ASAP! This party takes places on the Spirit of Boston, and cruises along Boston Harbor at night.
Climb aboard in your best Halloween costume, and enjoy 4 decks of fun. The party is led by the best DJ’s in Boston, so you can dance the night away while taking in the best nighttime skyline views.
28. Head Of The Charles Regatta
One of the most famous fall events in Boston is the Head of the Charles Regatta, and while it takes place in nearby Cambridge, it’s so easy to experience during a fall trip to Boston.
This regatta is actually the world’s largest 2-day rowing event, and this is where the best of the best compete in rowing championships along the Charles River. It’s such a fun thing to experience in person, and because the views of the river are so special in the fall season, it’s also a great way to enjoy autumn in Boston!
29. Harpoon Dogtoberfest
Okay, so probably the cutest fall event in Boston is the Harpoon Dogtoberfest, which is held in October each year.
If you’re traveling to Boston, you probably won’t have your furry friend with you, but that doesn’t mean you can’t be an enthusiastic spectator 😀 And if you’re in the Boston area, I encourage you to participate!
During Dogtoberfest, participate in a pup costume contest, or a 3-mile walk/run/trot/jog – whatever your pup’s speed is. Proceeds from the event go toward local charities, and honestly, what’s not to love about giving back AND seeing dogs in costume?
Bonus: Harpoon Octoberfest (For Humans 😉)
Looking for the human version of Octoberfest at Harpoon? I’ve got you covered! There’s one of those, too. Usually in late September, the brewery hosts this event, and has live music, plenty of beer, lots of food, fun contests, and tons more.
30. Harvard Square Oktoberfest
For over 40 years, the Harvard Square Oktoberfest has been a fall tradition in the Boston area. While the Harpoon Octoberfest is for those 21+ only, the Harvard Square Oktoberfest is a family-friendly event that appeals to everyone.
Enjoy awesome food vendors, live music, craft vendors and lots more!
31. Boston Public Market Harvest Party
Lastly, a wonderful fall event to have on your radar is the Boston Public Market Harvest Party, which also takes place in October each year.
During the Harvest Party at the Market, enjoy bites from local vendors, craft drinks featuring local spirits, live music, and an array of awesome vendors. Proceeds of the event go toward the Community Engagement Fund, which is a local organization that works to offer free events at the Market.
Where To Stay In Boston
Boston Harbor Hotel: For a high-end stay, this 5-star hotel on the waterfront is hard to beat. With on-site dining that includes an awesome cocktail bar, a pool, and gorgeous rooms, it has everything you need for a relaxing fall getaway.
Revere Boston Common: A great location that’s just steps from Boston Common, Beacon Hill, and the Public Gardens. There’s also a fun rooftop bar, on-site dining, free admission to the Paul Revere House, and modern rooms.
The Godfrey: Also a great location that’s a short walk to Boston Common, Beacon Hill and the Public Gardens. The plaid headboards in the modern rooms are the perfect fall decor for your trip, and they also have Polaroid camera available for guests to use during their stay!
Fall Weather In Boston
As mentioned earlier in the post, fall is one of the best times (if not the best) to visit Boston. The weather will likely be perfect. While you’ll want to anticipate some warmer weather, especially if you visit earlier in October, you can generally expect very comfortable temperatures ranging from 60-65°F.
You’ll also want to prepare for rain on a fall Boston trip, as October and November both have about 7-9 days of rain per month. However, it’s very possible you could luck out and have sunny weather the entire time.
I mention this in almost all my posts about weather in New England, but it bears repeating – weather in this region is moody, and changes frequently. So it’s best to check weather reports a few days before leaving to get a better idea of what to expect during your trip.
Is Boston In The Fall Season Expensive?
Unfortunately, yes, as are many New England destinations in the fall season. Boston is an expensive city year-round, but factor in fall foliage and its proximity to Salem, and you’re very likely to see price jumps in hotels. Expect to pay about $250-$350+ per night at a hotel in Boston.
You can, of course, find deals outside of the city, but even in Cambridge, it’s going to be higher than most other places around the country.
What To Pack For Boston In The Fall
Here are some helpful things to add to your packing list for your fall trip to Boston:
- Waterproof sneakers or boots in case of rain
- In fact, unless you plan to visit really fancy restaurants, I would leave your heels at home. Boston is a pretty casual city, and with the uneven cobblestone streets in many areas, a cute pair of booties will do the trick for pretty much any occasion.
- A nice, casual dress and jacket will work perfectly for a dinner out (again, unless it’s a very fancy place with a dress code, which is unlikely).
- A rain jacket that’s waterproof.
- Sweaters and jeans – this is what I usually live in when visiting Boston in the fall season.
- If you’re anticipating both warm and cool weather, pack some t-shirts that you can wear under sweaters to create light layers.
- Beanies and scarves if it’s forecasted to be cold.
- Reusable water bottle to stay hydrated while you walk around.
- Dramamine if you’re planning on a whale watch or cruise, and tend to get seasick.
- Day pack for any day trips you’re planning.
More posts you may also enjoy:
- Your Ultimate Guide To New England In The Fall
- Best Things To Do In Massachusetts In The Fall
- Best New England Ghost Tours
- The Perfect New England Fall Road Trip Itinerary
- Best Stops To Make On A Boston To Stowe, VT Road Trip
- Is New England In November Worth Visiting?
- Thanksgiving In New England: Cozy Getaway Ideas & Things To Do!
That’s A Wrap On Things To Do In Boston In The Fall
And there you have it! All my insider tips on the best things to do in Boston in the fall. Whether you’re using Boston as the starting point for an epic fall trip around New England, or it’s the home base for your trip, there are so many wonderful fall things to do that allow you to embrace the very best things about this magical time of the year. 🍁🍂🍁