Even though it’s New England’s largest city, there’s no shortage of fall coziness to be had in Boston! It’s honestly one of my favorite places in New England for a late-fall, or Halloween getaway. Between cobblestone streets covered in fallen leaves, amazing Halloween decorations, gorgeous foliage walks along the river, and cozy corners to sip a coffee, it really just ticks all the boxes for everything you’d want in a city fall getaway.
After many years of exploring Boston in the fall, this post is about all my suggestions on the top things to do, the best places to see foliage in the city, fun and easy fall day trips, and awesome spooky tours to take through the more haunted streets and neighborhoods.
And with that, let’s start planning your fall escape to Boston!
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Best Things To Do In Boston: Fall Foliage Spots
1. The Esplanade
It’s hard to pick one favorite foliage spot in the city, but if I had to, I would tell you to prioritize the Charles River Esplanade. It’s got a bit of everything in terms of skyline views (looking over at Cambridge), easy access to Boston’s skyline views, great walking paths, views of the river, beautiful bridges, and floating docks. All of which look especially perfect during foliage season here.
Plus, along the Esplanade, you’ll find lots of fall trees, including, maples, birch, oak, and more. I love that you get a mix of reds, yellows, and oranges while walking along a river – in a major city. It’s a really great experience, and one I do every fall visit I take to Boston.
My favorite access point to the Esplanade is at the Charles and Cambridge St. intersection in Beacon Hill. From there, you’ll see a really pretty building covered in ivy that also changes colors in the fall.
Then, walk onto the Frances Appleton bridge, which takes you to the Esplanade, or over to Longfellow Bridge (which is the next spot on my list 😉). From here, you can walk almost the entire length of the Esplanade, but you’ll also have the option for a shorter walk, since there are a few more access points back to the city.
2. Longfellow Bridge
Longfellow is one of my favorite little gems that a lot of visitors miss. This is the bridge that connects Boston’s Beacon Hill neighborhood to Cambridge, and it’s one of the best ways to take in views of the city skyline without having to go all the way to Cambridge.
It’s also steps from the Esplanade. In fact, you can easily take a staircase over to the bridge from the Frances Appleton bridge, and walk along the Longfellow first before heading to the Esplanade. Or, vice versa of course!
3. The Public Gardens
The Public Gardens is a must-visit any time of the year in Boston, and fall is no exception. To me, the Gardens are easily one of my top three spots in the city, and in the fall, you’ll see plenty of fall color to go around.
There are a variety of fall trees here as well, so you’ll usually be able to see colors ranging from reds and oranges, to vibrant golds.
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!
4. 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. There are actually more trees in the Common because it’s larger, so you tend to feel the impact of fall color here more.
I always combine these two spots on my fall trips to the city because they’re right next to each other.
Pro Tip: Most Freedom Trail tours also begin at the Common, so if you’re planning to do a guided tour, or a self-guided tour, it’s a great idea to plan your day accordingly by visiting the Gardens and Common before or after your tour.
5. Arnold Arboretum
Just outside of downtown, it’s only a quick drive or ride on the orange line via the T to get to the Arboretum. And this is such a beautiful spot for foliage during the fall season on Boston.
Home to over 500 maple trees, plus 1 out of every 15 trees at the Arboretum being an oak tree, you’re pretty much guaranteed fall color when you visit.
Two especially great spots for foliage here are Peter’s Hill, which offers a lot of color with a distant view of the skyline in the background. Then, I’d also recommend Meadow Road, which has several large maple trees lining the road for a really impactful view.
Pro Tip: The Arboretum is free to visit for everyone, and if you drive, expect parking on the weekends during peak foliage to be a challenge. However, parking on weekdays is easier. The T station is about a 5 minute or less walk from the park.
Fun Things To Do In Boston In The Fall
6. See The Beacon Hill Halloween Decorations
I like to plan my Boston fall visits for later in the month to see the best fall foliage, but also to enjoy all the festive Halloween decorations in Beacon Hill. This neighborhood is not only one of the most picturesque parts of the city, but it also truly goes all out.
My photos don’t do it justice because it really comes alive at night (and I don’t have any great night photos). But people here really take Halloween decorations seriously. You’ll see everything from classic stoops filled with pumpkins and mums, to skeletons and witches creeping in gardens.
The best night to visit (if it works with your schedule) is Halloween. Having walked around Beacon on Halloween night to see everyone’s more elaborate displays with lights, animatronics, sound effects and music is such a memorable experience. The trick-or-treaters have it so great here!
If Halloween isn’t quite your thing, or you visit earlier in the month, Beacon Hill is packed with all kinds of cozy vibes, and perfect for a fall afternoon stroll.
7. View Boston
View Boston is the observatory deck at the top of the Prudential Center, which is the second tallest building in the city. They’ve done a fantastic job creating a really nice observation area that offers incredible views of the Charles River, and surrounding downtown Boston. In the fall season, you get a different perspective of the foliage, too, which you’ll see lining many of the streets.
View Boston has two levels, one of which is indoors, and the other outdoors – and you’ll have access to both with your admission ticket. Additionally, there’s a bar for drinks, and it’s known as an especially great sunset location (keep in mind that sunsets during foliage season can get quite crowded up there, though!).
At the end, be sure to take some time to see the giant model of Boston, which is set to a very cool light show. My description makes it sound kind of lame, but it’s honestly very impressive. You’ll pass it on your way out.
8. See The Giant Pumpkins At The Public Market
Located inside the Public Market food hall, it’s a tradition to bring in the giant pumpkins in the fall season to help visitors get into the spirit of harvest season. They always set up the pumpkin as a cool photo spot, too, so it’s worth popping over to check them out, and then pick up some treats inside the food hall.
Inside, there are quite a few different vendors, some with perfect fall treats. First is Red Apple Farm, which serves cider and cider donuts. The other is Union Square Donuts, which usually has these cute spider donut in October for Halloween.
9. Sip & Munch On Fall Flavors
It’s not fall until that pumpkin spice latte is in your hand, right? 😂 There are so many great coffee shops in Boston for seasonal drinks, and one of the best things to do is grab whatever your fall drink of choice is before heading out to see the sights.
Tatte (pronounced like latte😉) is one of the more well-known cafés in Boston, and they’ve now expanded to several locations around the city, and beyond. The interiors are beautiful, the drinks, food, and baked goods are awesome, and it’s one of those places that doesn’t seem to let me down. Also, I love their apple turnovers in the fall!
George Howell is another great coffee shop in the city for a pumpkin spice latte, as is Little Wolf in Seaport (which is roasted on the North Shore and truly makes excellent coffee). If you’re looking for something a little more fun, the TravelMug Café in Seaport does latte flights to reflect the season, and their fall line-up always sounds really festive.
For comfort food, I always love to stop into Parish Café, specifically for their tomato soup, which they top with grilled cheese croutons (which are basically tiny grilled cheese sandwiches). It’s one of those things in the fall and winter season that just always hits right. They usually have really nice seasonal cocktails, too.
There are tons of places to check out for a fall seasonal menu in Boston, of course. These are just a few that I tend to come back to over and over.
10. Cozy Up At Abigail’s Tea Room
A lot of people miss this, but inside the Boston Tea Party Museum is Abigail’s Tea Room, and it’s a place you can visit separately from the museum. In the fall and winter season, it’s one of my absolute favorite places to visit because it’s so cozy inside, and usually has a very relaxed vibe.
Named after Abigail Adams, President John Adams’ wife, the tea room features a self-serve unlimited tea option, which has the same varieties of tea that were famously thrown into the harbor. They typically have five teas available to try, and you can refill your cup as many times as you want. The cost is also pretty inexpensive for the experience, I think.
The room overlooks the harbor, so regardless of the weather, you can stay cozy inside and admire the waterfront scenery.
Pro Tip: To find the tea room, go inside the museum gift shop, and walk all the way to the back left corner. You’ll see a door that leads outside to a dock that connects to the tea room.
Spooky Tours In Boston Perfect For The Fall Season
11. 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.
🍁 Click here to check out the Ghosts & Gravestones Trolley Tour
12. Haunted Pub Walking Tour
The Haunted Booze & Boos Pub Tour is perfect for those looking for a good mix of fun, history, a few scares … and drinks! 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.
🍁 Click here to check out the Haunted Pub Tour
13. 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.
🍁 Click here to check out the Death & Dying Tour
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 worth the excursion or day trip. These are the destinations I recommend if you’re looking to add a day trip or two to your fall Boston itinerary.
14. 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.
It’s really important, though, that you know how crowded Salem is during the month of October. Especially on the weekends. And it’s the most crowded on either the weekend before Halloween, or Halloween night. During my first-ever October visit to Salem, I wasn’t prepared for the crowds, and I didn’t enjoy it that much. I went back the following year with better expectations and more planning, and I had a blast. However, if crowds really bother you, this is something to really consider.
To get to Salem from Boston in October, I recommend avoiding driving in, if you can. The train and the ferry are far better options, both of which allow you to forgo the challenge of finding a parking spot. If you’re visiting on a weekend in October, I wouldn’t even think about driving in unless you’re planning to arrive very early in the morning.
Psst! I have some helpful guides including planning the perfect Salem, MA day trip, and the best time to visit Salem if you need more information 😉
15. Lexington & Concord
As part of the greater Boston area, this is another day trip option that’s so easy to explore from Boston. Both Lexington and Concord have lots of beautiful foliage to see, historic places, and a quaint downtown area that serves as a perfect escape from the busy city.
Here’s what I suggest checking out in this area in the fall:
Minute Man National Historical Park, which is home to about 9 miles of trails, showcasing really nice foliage, scenic walks through the woods, and historic houses along the way. It’s also home to the Old North Bridge, which is worth seeking out.
Downtown Concord, which is the perfect spot for some pretty foliage, but also very cute shops, and is a great place to plan to have lunch.
Louisa May Alcott’s Orchard House, which the home of the famous author of Little Women.
Walden Pond, made famous by Henry David Thoreau’s book. This is also a great foliage spot.
Wilson Farms, which is one of my favorite farm shops in New England. I always go here when in Lexington. They’re famous for their pumpkin wall, which they put up every other year. But even if you’re not there on a year the pumpkin wall is up, they also have the pumpkin village, tons of pumpkins available for purchase right at the store (seriously – I’ve never seen such a big selection!), and a fantastic farm store inside with a bakery and all kinds of great stuff.
16. Marblehead
Marblehead is so close to Boston, but yet, feels words away. It’s truly one of my absolute favorite places in New England.
This coastal town borders Salem, and tends to be quieter and more relaxing than Salem in October. But, you’ll still see some beautiful foliage here, making a fantastic fall day trip.
I have an entire post on things to do in Marblehead, MA to help you plan your itinerary.
17. Sturbridge
Sturbridge is a cool spot to check out in the fall, and is most well-known for being home to Old Sturbridge Village, a living history museum. Set-up to feel like you’re stepping back in time, the immersive experience is an outdoor museum that’s set-up to reflect life in rural New England in the 1800s.
In the fall, the museum also hosts the very cool Phantoms By Firelight experience, which takes place around sunset and through the evening with different performances, and the main town area aglow with lanterns.
While there aren’t a ton more attractions in Sturbridge, I do recommend stopping at two other place: Tree House Brewing, which is one of the best breweries in the country, and Saw Dust Café, which has everything from coffee and baked goods, to cocktails and food.
18. The Essex Coastal Scenic Byway
If you’re looking to head out on a scenic drive in the fall from Boston, the Essex Coastal Scenic Byway is such a beautiful drive. Having done it during peak foliage, I was honestly impressed by how much fall color I saw. It’s not known for fall foliage, which is perhaps why I was so impressed. But, especially in and around Essex, Ipswich, and Newburyport, it was the perfect balance of coastal scenery and fall color.
The drive goes between Lynn and Salisbury, and also includes Marblehead, Salem, Rockport, Gloucester, Manchester-by-the-Sea, Ipswich, Essex, and Newburyport. You can easily do the drive in a day if you start early enough, and don’t spend too much time as many of the stops. To make it a manageable day trip, I’d pick 2-3 places to stop, and mostly just enjoy the drive along the way.
Where To Stay In Boston In The Fall
For any visit to Boston, I always recommend staying in the main downtown areas, close to the Public Gardens, if possible. This allows you easy access to most tourist attractions on foot, and you’ll be centrally-located to most everything on your itinerary.
Boston Harbor Hotel: For a high-end stay, this 5-star hotel on the waterfront is hard to beat. It’s a bit further from the Public Gardens, but you’ll be right on the harbor and close to Seaport and the Aquarium. 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.
🍁 Click here to check out the Boston Harbor Hotel
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. Parking here is also easy, as the garage is right next to the hotel.
🍁 Click here to check out the Revere Boston Common
The Godfrey: Also a great location that’s a short walk to Boston Common, Beacon Hill and the Public Gardens. This hotel tends to be more affordable than other places nearby, but rooms still feel updated and modern. Plus, George Howell coffee shop is attached to the lobby!
🍁 Click here to check out The Godfrey
Want a fully-planned New England fall trip?
Visiting Boston In The Fall: Answering Your Questions
When Should I Visit For The Best Fall Foliage?
Boston typically experiences peak fall color and foliage around Halloween. Depending on the year, it could arrive a bit earlier, but usually the last week of October, going into early November is the best time for foliage in the city.
What Is Boston Fall Weather Like?
I think you’ll absolutely LOVE fall weather in Boston – especially later in October. The average temperature is about 60-65°F – it’s usually closer to 65 in early October, and closer to 60 toward the end of the month. Of course, you could have slightly warmer or colder days, but generally, that’s what to expect.
You’ll also experience a mix of rain and sun, so it’s best to plan for rain, or double-check the weather forecast a day or two before leaving. Boston is also one of the windiest cities in the U.S., due to it’s coastal location, so I always like to tell people to prepare for lots of wind.
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. 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
Generally, you want to keep it casual. Boston is a casual city in general, especially with its large population of college-aged people. In the fall, my typical outfits include jeans, a t-shirt (long or shirt-sleeved, depending on the weather), a sweater or trench coat, and sneakers.
Boston is a very walkable city, especially where most tourists explore, and sneakers are a must to stay comfortable, and navigate those old, historic cobblestone streets. I also have a full guide on Boston fall outfit ideas and packing tips, if you need more info 😉
More posts you may also enjoy:
- Your Ultimate Guide To New England In The Fall
- Best Things To Do In Massachusetts In The Fall
- Wonderfully Romantic Getaways From Boston
- 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
- Boston In The Winter
- Thanksgiving In New England: Cozy Getaway Ideas & Things To Do!
- Driving Boston To New York City: Best Stops & Routes To Take
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. 🍁🍂🍁
