As the temperature drops and the leaves change colors, Boston is looking positively picturesque at this time of year. And with Halloween just around the corner, there are tons of activities to take part in around the city this October!
From festivals to nature walks, here are our recommendations for plans this month:
1. Journey to space at this immersive exhibit about the Apollo missions
The Moonwalkers: A Journey with Tom Hanks landed in Back Bay. Enjoy a dazzling 60-minute audiovisual show that includes a journey to space narrated by Oscar-winner Tom Hanks, NASA footage, and more! Secure your tickets here.
2. Take a spooktacular mystery picnic with friends
What distinguishes a foodie from a mere mortal?
Adventure!
Enjoy the ultimate foodie adventure as your taste buds, and mind get to experience the thrill of a mystery picnic. Solve clues that’ll lead you to your ultimate destination where an extravagant picnic awaits! Reserve your adventure online.
Back Bay & Downtown Boston Mystery Picnic: Self-Guided Foodie Adventure
3. Light up the mood with a Candlelight concert
Imagine sitting in the warm glow of a thousand candles, with a live orchestra softly strumming classic tunes in an ornate historic building. Candlelight concerts mesh the magic of live performance with a multi-sensory musical experience for a jaw dropping performance! October brings two unique Candlelight experiences to Boston.
- If you’re in for a spine-chilling musical performance, check out the Haunted Evening of Halloween Classics!
- If you’re a Swiftie you’ll love Candlelight: A Tribute to Taylor Swift for the ultimate fall vibes
Some of these limited-edition Candlelight experiences only take place in October! Tickets are selling out fast for showtimes, so make sure to secure a seat!
Candlelight: Tribute to Taylor Swift - 4.68 · 104 reviews
4. Try a mysterious and sensual blindfolded dinner
How savvy are your taste buds? Get out of your comfort zone this spooky season with a mysteriously amusing 3-course blindfolded dinner. Learn more and grab tickets here.
Dining in the Dark: A Unique Blindfolded Dining Experience at Premiere on Broadway - 4.44 · 260 reviews
5. Visit this once-in-a-lifetime 360° immersive Monet experience
This is Monet like you’ve never seen it before! Combining the power of VR, projection mapping and digital displays, explore Monet’s works in larger-than-life form! The exhibit spans 60-90 minutes and takes place at Mercantile Center in Worcester. After, make sure to grab a bite at the famous Birch Tree Bread Company and fuel up with a coffee at Fuel America! Learn more and reserve tickets here.
Monet: The Immersive Experience - Worcester - 4.42 · 606 reviews
6. Explore Massachusetts’ spookiest town, Salem
Just 17 miles north of Boston sits the small, quaint town of Salem: a place known for its ghosts, mysterious energy and, of course, its famous witch trials. From haunted spots and historic sites to magic shops, we’ve come up with a few magical Salem spots to explore and bask in the city’s witchy spirit. Check out our full guide to exploring Salem here.
7. Catch the fall foliage at the best rated spot in Massachusetts
Planning a trip to the countryside to catch the leaves changing colors this fall? Lenox, MA should be on your itinerary. According to Reader’s Digest, this Berkshire town has some of the most vibrant fall foliage in the country. Starting in late September, the area’s landscapes are ablaze with reds, yellows, and greens. Read more here.
8. Or explore a hidden waterfall in Vermont, surrounded by changing trees
Tucked away in Warren, VT, these falls are the perfect natural spot to escape the leaf-peeping crowds. A wild swimming spot may not sound like the most appealing fall destination but hear us out. If you’re looking to escape the throngs of leaf-peepers currently exploring the New England wilderness but still want to bask in the glorious fall foliage of the area, this is the place for you this fall. Details here!
9. Get lost in a corn maze
Before escape rooms were all the rage, corn mazes were (and still are!) the best places to have fun and solve a massive outdoor puzzle with your friends. Bring family and friends for a day of trial and error as you navigate your way through fields of corn as far as the eye can see at a corn maze close to Boston.. Here are some ideas:
- Hanson’s Farms in Framingham
- Marini Farm in Ipswich
- Connors Farm in Danvers
- Sauchuk’s Corn Maze and Pumpkin Patch in Plympton
- Davis Mega Maze in Sterling
See the rest of the best corn mazes in Boston here!
10. Cheer on the Head of the Charles athletes
The Head of the Charles regatta returns October 17-19 this year. It’s a fun spectacle to cheer on the rowers from these five iconic HOCR viewing spots.
11. Go on a beautifully haunting hike through an abandoned ghost town
A spookier alternative to the classic autumn nature walk is exploring one of Massachusetts’ ghost towns. As our state is home to some of the first settlements in the United States, it’s no surprise that there are plenty of ghost towns around. Whether the original inhabitants abandoned the villages over decades or were forced to leave, there’s plenty of interesting history remaining for you to explore on a hike through ages past.
Check out the eerie magnificence of these towns:
- Dogtown
- Catamount
- Quabbin Reservoir Towns
- Long Point
- Whitewash Village
- Davis
View our full itinerary of Massachusetts ghost towns for a solidarity staycation.
12. Go glamping in the great outdoors
Fall weather can be unpredictable, but you can bet that a glamping experience is sure to be a comfortable getaway in nature this fall. Glamping (glamorous camping!) provides all the beautiful scenery of the outdoors without sacrificing modern amenities. Luckily there are tons of glampsites around New England such as:
- Getaway in Epson, New Hampshire
- Normandy Farms in Foxborough, Massachusetts
- Maine Forest Yurts in Durham, Maine
- Tops’l Farm in Waldoboro, Maine
- Sandy Pines Campground in Kennebunkport, Maine
- Huttopia White Mountains in Albany, New Hampshire
- Autocamp in Cape Cod
While some require long car rides away from the city, the trek will absolutely be worth it. Check out our top picks for glamping outside of Boston for a lovely fall getaway.
13. Thrift shop for some seriously spooky Halloween costumes
Want to assemble a perfectly spooky Halloween fit? Look no further than your local thrift stores—thrifting is one of the best options to shop for Halloween costumes without breaking the bank, and Boston has no shortage of super-cool thrift shops where you can browse around. Our list of fun Boston thrift stores includes boutiques and chains of all price ranges and styles, but no matter where you go, you’ll be certain to leave with a Halloween costume that’s completely unique.
14. Try out a new restaurant
There’s a plethora of new spots opening in Boston this fall, but Boston also has some tried-and-true restaurants you need to visit at least once. Visit one of these essential Boston restaurants.
15. Revisit a fall classic: the Apple Cider doughnut
It’s that time of year when local orchards and bakeries start serving those steaming hot, cinnamon-dusted delicacies we call apple cider donuts. When you’re craving a fresh-baked doughnut, you don’t have to travel too far to satisfy your cravings. Check out our list of the best places in in the city to get one (or a dozen), including:
- Blackbird Doughnuts
- Kane’s Donuts
- Wilson Farm
- Union Square Doughnuts
- Volante Farms
16. Head out to the Flannel Jam fall music festival
Folk stars ring in the fall with a cozy, comfy music fest. The 3-day festival will take place in Marshfield and on Nantucket. “One percent of each ticket sold will be contributed to the Levitate Foundation, a non-profit whose mission is to cultivate vibrant communities by creating and conserving access to music, art and the outdoors.” Find the New England Flannel Jam October 11-13 during Columbus Day Weekend!
17. Get salty with the New Bedford Whaling Museum
There are many upcoming events and exhibits this month at the museum. New to this museum this October is a presentation exploring Cape Verdean Independence on October 1.
18. Check out the free Play it by Fear spooky season concert
Enjoy live musical scores of spooky classics like Ghostbusters, The Twilight Zone, Stranger Things, and The Addams Family, along with scores from beloved, festive family classics like The Nightmare Before Christmas and Harry Potter. Find more details and reserve your free admission online.
111 Harbor Way, Boston, MA 02210
19. Get inspired at the Chinatown Arts Festival
Now through October 17 explore the colors of Boston’s Chinatown. The rich artistic history of old and new is on display with 8 bold window murals, on bright display throughout the neighborhood! Murals on display throughout Chinatown by local artists. This year’s theme is ” Imagine a Greener Future for Chinatown.”
20. Make strides against breast cancer with the American Cancer Society
October is Breast Cancer Awareness Month. On October 5 at the Hatch Shell will be the 33rd annual Making Strides Against Breast Cancer walk, where over 3,000 survivors, thrivers, and caregivers will dress in pink and parade around the Esplanade to honor those who are no longer here to walk. All month long there will be events to raise awareness honor survivors and encourage women to learn about early detection.
21. Get cozy in a New Orleans inspired jazz club
Boston has a top tier supply of jazz clubs, and what better time of year to cozy up to the smooth sounds of jazz than as the seasons begin to turn. Scullers Jazz Club, loved for their showcasing of everything from classic to Latin and contemporary jazz, is hosting a new series of jazz events which pay homage to the birthplace of the genre, 1920s New Orleans, by recreating its street-style bars and with the songs of Louis Armstrong and Fats Waller. What better way to welcome in the darker nights!
21. Wake up with a Pumpkin Spice Cold Brew from Blank Street
It’s pumpkin spice latte season, but let’s be real, most New Englanders are going to have the iced coffee or cold brew version- even as the temps dip. Blank Street released its Shaken Pumpkin Spice Cold Brew just in time!
The mix of pumpkin pie spice, cold brew, and milk taste like a crisp fall morning in a cup! Fun fact, the latest edition of its innovative and delicious Cold Brew Menu: The Shaken Pumpkin Spice Cold Brew from Blank Street sells 3x more than the regular Blank Street Pumpkin Spice Latte!
22. Enjoy a special Oktoberfest menu in the city
Restaurants around Boston are switching things up with fabulous Oktoberfest dinners! Here are a few spots to check them out:
- The Nautilus
23. Have the perfect girls getaway at Red Jacket Resorts
Red Jacket Beach Resort on Cape Cod is hosting its annual Girls’ Weekend from October 24-26, inviting women of all ages to enjoy a fun-filled retreat with specialty programming and coastal activities. The weekend features a variety of events, including food offerings, music, and opportunities for relaxation, with rates starting at $664 per gal. This newly renovated resort provides a memorable experience celebrating friendship and the changing season. Grab the gals and get ready for a weekend of glam-emories!
24. Join the Boston 10K for Women
Let’s race! Boston 10K for Women, taking place annually on Columbus Day, on Beacon Street in Boston marks a Boston tradition since 1977. The race by women, and for women empowers them to become the fastest and farthest reaching version of themselves—learn more or register.
25. Go apple picking at a tranquil orchard
Apple picking is the quintessential fall activity in New England. What’s better than exploring picturesque apple orchards, picking your own, and taking a bag home to enjoy in a homemade apple pie or just by themselves? Our list of the ten best orchards will definitely get you motivated to plan a weekend excursion outside the city.
- Brooksby Farm in Peabody
- Boston Hill Farm and Smolak Farms in North Andover
- Lookout Farm in Natick
- Dowse Orchards and in Sherborn
If you want a pick at some of the best apples in the country, according to USA Today, then head to this farm in Northborough, MA!
26. Box for a good cause
In recognition of Mental Health Screening Month and World Mental Health Day this October, Rumble Boxing and Happiness Project partner on a new campaign Not Every Fight Is Visible. Throughout the month of October the Watertown and Somerville locations feature co-branded apparel, community events, and Rumble Boxing members can bring friends to class for free all month!
27. October babies, get a free lobster
Libras and Scorpios you’re in luck! Summer Shack in Alewife is switching things up. Visit the seafood spot to celebrate an October birthday, and enjoy a complimentary 1-pound lobster with a valid ID.
28. Spend the perfect Saturday evening on the Blue Hills
A sunset hike, hilltop concert, and fall foliage. Name a better combo for a Saturday afternoon? One of the best fall foliage hikes right outside Boston, with views of the skyline, will be the backdrop for the Friends of the Blue Hills 2025 Sunset Hike & Hilltop Concert. Cover band Retro Rockets serenades guests at 5:45.
Bring-your-own picnic! Find it October 11 from 4:30-6:30 and reserve your spot.
29. Check out the new exhibit at the ICA, An Indigenous Present
Seaport’s ICA presents An Indigenous Present, a nationally touring thematic exhibition spanning 100 years of contemporary Indigenous art. The exhibition includes works by 15 artists utilizing abstraction to represent personal and collective narratives, describe specific and imagined places, and build upon cultural and aesthetic traditions. An Indigenous Present debuts at the ICA on October 9 and remains on view through March 8, 2026.
30. Meet author Elin Hilderbrand and chat about her new book
The queen of Nantucket takes us to a a new setting this autumn. Hildebrand’s newest release “The Academy,” is not only special because of its setting in a New England Boarding School, but Elin co-authored the book with her daughter, Shelby Cunningham.
Learn all about the real-life boarding school stories that inspired “The Academy,” what it’s like writing with your daughter, and more, with Elin at the Spire Center on October 20. Tickets are going fast! Reserve your spot.
31. Attend the Health Equity International 2025 Celebration in Back Bay
Health Equity International, based in Somerville, has been providing essential healthcare and services in Haiti for more than 40 years. The core of their mission takes place at St. Boniface Hospital, the largest fully functioning hospital in Haiti that remains a critical lifeline.
On October 23 from 5:30-7:30 HEI hosts a fundraising Gala and celebration at Saint Cecilia Parish in Boston. The evening will also honor Sharon McNally, CEO of Camp Harbor View, for her extraordinary commitment to supporting vulnerable communities in both southern Haiti and greater Boston. All ticket proceeds benefit HEI and can be purchased here.