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There truly is no place like New England in the fall. From apple orchards and homemade cider donuts to pumpkin patches and the spookiest decor, this is definitely my favorite season in the area. I specifically love October, but September – November is an amazing time to visit the region. If you’re hoping to catch peak foliage in New Hampshire and Vermont, be sure to book your trip in late September and early October. If you want to catch Halloween decor and foliage around Boston, visit in mid-late October. Similar to my guides covering 25 things to do in Boston during the summer, things to do during the winter, and things to do in Boston during the spring, this guide is going to focus on the autumn season. Here’s your fall Boston bucket list, broken down by neighborhood.
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Cambridge
While not *technically* the city of Boston, Cambridge is just across the river and should absolutely be explored during this time of year. Here are my favorite fall activities to do around Cambridge…
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1. Stroll Through Harvard Square
Harvard is just meant to be explored during the autumn season. Not sure if ititss because of the fall leaves that descend around the brick buildings, or the Crimson red colors, but the campus really pops this time of year. I recommend taking a student-led tour to learn about the history + academics of the university. Make a day of it by grabbing brunch at Daily Provisions and a pizza dinner at Source too!
Pro-tip: Harvard Square is scattered with quaint boutiques and school spirit stores. The Harvard Shirt Shop is a great place to buy merch!
2. Visit Mount Auburn Cemetery
I think this is the first time I’m recommending to walk through a cemetery on this blog (actually, perhaps I did in New Orleans!), but this is really a beautiful thing to do during the fall in Boston. This park has some of the best fall foliage in the area and packs in the spooky vibes. Visit at dusk / sunset for the full effect.
3. Enjoy A Free “Night At The Museum” Party
At the end of every month, Harvard Art Museums hosts a FREE museum party! If you happen to be in Boston on the last Thursday evening of the month, head to this free museum to stroll through 3 floors of galleries, grab a drink, enjoy a bite of food, and listen to music from a DJ! Although this event happens year-round, it’s super cozy, so I recommend visiting in the fall or winter months.
4. Browse Lovestruck Books
Known as “Boston’s best bookstore”, this book shop is like nothing else I’ve ever seen. It’s entirely romance-themed (and very pink!). Grab a cappuccino or visit in the evening for their wine pairing. I can’t think of a better place to hangout during a chilly fall day!
Downtown Boston
5. Fall Movies On The Greenway
Boston has so many incredible free, outdoor movie nights! However, these fun events (which often include free popcorn) don’t end when the summer does. Head to the Greenway in September and October for their free fall movie nights. Catch fan-favorite flicks like Halloweentown on the big screen.
6. Celebrate Oktoberfest At Sam Adams
Head to one of the city’s many breweries for Oktoberfest in September! Despite the name, this world-wide beer event actually begins in mid-September. While there are events at many breweries around Boston, Sam Adams puts on one of the largest Oktoberfest events in the city!
Back Bay
7. See Halloween Decor On Comm Ave
Back Bay is one of the best neighborhoods in Boston for Halloween decor. I specifically love strolling down Comm Ave & Marlborough St this time of year. Grab your camera and get ready to see creepy clowns, Egyptian skeletons, and everything in between.
8. Trick-or-Treat On Marlborough St
Marlborough St is known for being one of the most photographic streets in Boston. It’s also situated in one of the most affluent areas of the city, meaning it’s pretty much a gold mine for trick-or-treaters. Whether you’re visiting on October 31 or not, this street is a beautiful place to stroll, however, it really comes to life on Halloween (hint: big candy bars expected)!
Fenway-Kenmore
9. Watch Head Of The Charles From BU Bridge
Each October, Boston hosts the world’s largest 3-day regatta. The Head of the Charles is a full weekend event that draws crowds from all around the country & athletes from schools all around the world. One of the best places to watch the races is from the BU Bridge, located on the Boston side of the river, by the BU campus. You can easily get here from Back Bay by enjoying a scenic walk down the Esplanade.
Beacon Hill
10. Go For A Spooky Walk Through Beacon Hill
Aside from Back Bay & South End (honorable mentions), Beacon Hill has some of the best halloween decor in Boston! Every year, the charming brick row homes go all out — putting out spooky displays for people of all ages to enjoy. I recommend walking down Mount Vernon Street and Brimmer Street in Beacon Hill for the most elaborate displays.
11. Visit Acorn Street
Did you know that Acorn Street is the most photographed street in the USA? It’s beautiful year-round, especially during the summer, but really comes to life during the autumn season since it’s surrounded by fall foliage. You can see Acorn Street, the above Halloween decor, and adjacent Louisburg Square all in one visit.
Seaport
12. Try A Spooky Latte
There are many incredible coffee shops around Boston, but one of my favorites has to be Travel Mug Cafe in Seaport. Located right on the water, this cafe also shares a space with a creative writing center and bookstore, aka it’s one of my favorite places ever. They also serve up fabulous seasonal lattes! Be sure to try their spooky coffee flight, which features a ghost latte, maple-flavored syrups, cinnamon deliciousness, and so much more.
13. Get A Pumpkin Treat
Lakon Paris Patisserie in Boston’s Seaport highlights the best of fall with a rotating menu of seasonal pastries and desserts. You’ll find buttery croissants in flavors like pumpkin spice, maple pecan, and caramel apple, along with the best espresso drinks and speciality tiramisu lattes.
South Boston (Southie)
14. See The Southie Haunts House
Every fall, this one home in Southie puts on quite the show. Walk by and snap some pics of the Halloween decor, it’s sure to get you into the autumn spirit!
15. Pumpkin Spice Espresso Martinis
Capo is a popular Italian restaurant in Southie with a fun basement for nightlife (if you are under the age of like 26). During the fall months, they offer a “Pumpkin Espresso Martini” as a seasonal drink made with vodka, cold brew, cacao, Galliano Espresso, and a house-made pumpkin cream. This cocktail is a popular seasonal offering and is 100% worth trying!
16. Fall Lattes At Cannonball Cafe
Another must for this time of year is Cannonball Cafe, a fan-favorite coffee shop located in South Boston! This cafe is known for their craft lattes and delicious breakfast sandwiches. I’ve been here a few times, and it never misses. I recommend visiting mid-week if you can to avoid the weekend long lines, but regardless, this spot definitely deserves a spot on this things to do in Boston during the fall list.
Picture: pumpkin s’mores lattes apple cider chai, caramel apple butter cold brew, and MORE!
South End
17. See Halloween Decor Around Union Park
Similar to Back Bay and Beacon Hill, the South End neighborhood is scattered with spooky Halloween decor. Check out Brookline Street and Canton Street for the most elaborate displays. Union Park is also worth seeing, as it’s one of the most Instagrammable places in Boston.
18. Eat A Cozy Dinner On The Capri Patio
Capri is Boston’s newest Italian restaurant and has one of the most stunning interiors and ambiances that I’ve ever seen. The Italian steakhouse has an outdoor fireplace and cozy lamps on the bar. I definitely recommend grabbing a drink at the bar and then cozying up by the fire for a glass of red wine and pasta bolognese.
Greater Boston
19. Go Apple Picking
Each September is apple picking season in New England! There are dozens of apple orchards and farm stands around Boston, but my personal favorites are Cider Hill in Amesbury, Honey Pot Hill Orchards in Stow, and Smolak Farms in Andover. Each of these farms has apple cider donuts, apple cider slushies, and offer apple picking, hayrides, pumpkin patches, and have farm animals.
20. Day Trip To Salem
Since Salem is only 30 minutes north of Boston, you MUST do a day trip to Salem for Halloween. Visiting Salem, Massachusetts in October is like stepping into a living Halloween movie — the whole city comes alive with spooky charm, crisp autumn air, and centuries of witchy history. This top-rated walking tour covers all the history and key spots around the city.
I recommend touring the Salem Witch House — which has an iconic exterior for photos and the nearby Salem Witch Dungeon Museum, which both offering fascinating glimpses into the 1692 witch trials. Wander Essex Street for unique shops, psychic readings, and street performers. Blackcraft has famous coffees, but you need a reservation to wait in the line.
Pro-tip: Avoid the crowds by visiting in late September, on a weekday, or in the mornings. I have a complete guide to visiting Salem, MA right here.
21. Concord Rail Trail
The Concord Rail Trail is a fantastic way to soak up New England’s fall scenery right outside Boston, and should be on your New England bucket list. This paved, flat path winds through Concord, Acton, and beyond, making it perfect for walking or biking through the foliage. Start near West Concord Village, where there are great spots to grab a coffee or lunch, like Nashoba Brook Bakery or Trail’s End Café. For history lovers, it’s easy to detour into Minute Man National Historical Park, where the first shots of the Revolutionary War were fired. If you love history, you should also stroll the Freedom Trail in Boston!
22. Lizzie Borden House Tour
I recently experienced an official Lizzie Borden House Tour with US Ghost Adventures, and let me say — this is definitely a spooky experience! Therefore, it deserved a spot on this list of things to do in Boston during the fall.
Located about an hour south of the city in Fall River, this home is known as being one of the most (if not THE MOST) haunted homes in the US. It’s where Lizzie Borden lived with her father, step-mother, and sister in the late 1800s, and where her parents were brutally murdered with an axe. Today, you can not only tour the home, but if you’re brave — you can actually STAY here as it’s also a historic B&B.
23. RailRiders Foliage Tour In Concord, NH
These last 3 recommendations are located outside of Massachusetts, but are still super accessible from Boston. The Scenic RailRiders tour is just one hour north of Boston in Concord, New Hampshire. Pedal for 5+ miles along an abandoned railroad, past a river, under a bridge, through a forest, and near a farm with cows! This is one of the most unique ways to see the foliage in New England.
24. Jack-O-Lantern Spectacular At Roger Williams Zoo in RI
Open nightly from late September through early November, the Roger Williams Zoo just outside of Providence, RI hosts the Jack-O-Lantern Spectacular every year. Walk along the famous Pumpkin Trail in the zoo and see over 5,000 beautifully carved jack-o-lanterns. They have food, drinks, and games / activities for all ages here. You can see the trail in less than one hour.
Pro-tip: The Pumpkin trail is open nightly from 6:00 – 10:30 pm, last entry at 10:00 pm. The Spectacular is open rain or shine, all tickets are non-refundable and cannot be exchanged for a different date.
25. Leaf Peeping Along The Kancamagus Highway
While the foliage around Boston is amazing and this is a bit far outside of Boston, I HAD to include the Kancamagus Highway on this list as Franconia Notch, NH really is one of the best places to visit outside of Boston during the fall. This area gets some of the best foliage in New England and would be a perfect girls weekend getaway. Popular hikes include The Flume and Artists Bluff in Franconia Notch State Park.
Peak foliage week is usually around Columbus Day Weekend, but that also means it’s peak week for crowds, so plan your New England fall road trip accordingly.
That brings us to the end of this guide covering 25 things to do in Boston and beyond during the fall. I hope this guide inspires you to plan some fun autumn adventures and day trips for many years to come!
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