As the crisp autumn air settles over Greater Boston, the region bursts into life with vibrant events and a strong sense of community. Whether you’re looking to enjoy seasonal flavors, experience the beauty of fall foliage, or dive into family-friendly activities, there’s something for everyone. Check out these can’t-miss fall events in Greater Boston!

Boston Fall Foliage Tours – October 1-31, 2025

Kick off your fall adventure by strolling through the Boston Public Garden during its peak foliage. These guided tours are a perfect way to take in the colorful scenery while learning about the history of this iconic spot.

Boston’s Wicked Haunt Fest (Charlestown) – September 29 – November 3, 2025

Get ready for Boston’s Wicked Haunt Fest, where Halloween magic comes to life! This vibrant festival features themed areas, unique seasonal treats, and an Octoberfest-style beer garden. Enjoy live performances, explore spooky vendor stalls, and let the kids get creative with pumpkin painting and family activities.

Bates School Pumpkin Fair (Wellesley) – October 4, 2025

The Bates School Pumpkin Fair is back and better than ever! Get ready for an afternoon filled with fall fun, including pumpkin decorating, exciting games, tasty treats, and more. Whether you’re enjoying the seasonal crafts, grabbing a bite, or trying your hand at carnival-style games, there’s something for everyone.

Harpoon Octoberfest (Boston) – October 3-5, 2025

Harpoon Octoberfest is Boston’s biggest fall party, featuring flowing taps, live oompah music, stein-hoisting, pretzel eating, and plenty of chicken dancing. Raise a stein under the tents or outdoors with thousands of beer lovers while enjoying a wide selection of beer, cider, and seltzer. Additional beer tickets and delicious food will be available to keep the celebration going.

Harpoon Dogtoberfest (Boston) – October 5, 2025

Harpoon Dogtoberfest is back, welcoming dog lovers and their furry friends to the Harpoon Brewery for a celebration of Octoberfest! Enjoy a day filled with fun activities while supporting a great cause—net proceeds benefit the Kenary Brain Tumor Research Fund at Dana-Farber Cancer Institute and MSPCA-Angell. Bring your pup and join in the festivities for a tail-wagging good time!

Newtonville Village Day –October 5th, 2025

Wrap up your fall event list with Newtonville Village Day. This vibrant street festival features live music, delicious local food, and crafts that celebrate the unique character of Newtonville.

HONK! Festival – (Somerville) October 9-12, 2025

HONK! is a bold street band movement bringing outrageous, inclusive, and brassy sounds to public spaces around the world. Blending influences from Klezmer and Balkan to Samba, Afrobeat, Punk, and New Orleans traditions, these bands play among the people-not above them-turning every performance into a celebration. More than music, HONK! is community, activism, and pure sonic joy, delivered with the spirit of Mardi Gras and Carnival.

HarvestFest at the Boston Public Market (Downtown) – October 16, 2025

Love fall flavors? HarvestFest is where you’ll want to be. This festival celebrates all things New England with local farmers, artisans, and mouth-watering seasonal treats. Don’t forget to check out the handcrafted goods while you’re there!

Newton Harvest Fair – October 19, 2025

For a family-friendly day out, the Newton Harvest Fair is a must. With live music, carnival rides, craft vendors, and tons of food options, it’s an event that’ll keep everyone entertained.

Doggone Halloween Pet Parade (Downtown Crossings) – October 25th, 2025

Boston’s annual Doggone Halloween Pet Parade is back, bringing pups and their owners in their spookiest costumes to Downtown Crossing. This free event includes a pet parade, vendor village, family-friendly activities, and prizes for standout costumes-from cutest to scariest, plus best human-and-dog duos. It’s the perfect way to celebrate Halloween and see the city’s furry friends strut their stuff!

Explore Greater Boston This Fall

Fall in Greater Boston offers the perfect blend of natural beauty, lively community events, and a welcoming atmosphere. Whether you’re considering a cozy city apartment, a suburban retreat, or simply exploring the area, Greater Boston has something for everyone. If you’re thinking about buying or selling a home, fall provides a beautiful backdrop to showcase properties. Connect with one of our agents today to explore your options in this vibrant region.

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