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!

1. Boston Public Garden Fall Foliage Tours – October 1-31, 2024

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.

2.) Sam Adams OctoberFest (Boston) – September 27, 2024

Get ready for Sam Adams OctoberFest, where we put our own twist on the centuries-old German beer festival tradition! Savor classic German-style brews alongside Sam Adams’ seasonal favorites in a lively setting filled with live music, mouth-watering food, and plenty of festive fall fun. Prost!

3. HarvestFest at the Boston Public Market – October 17, 2024

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!

4.) Boston’s Wicked Haunt Fest – September 29 – November 3, 2024

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.

5.) Harpoon Dogtoberfest – Boston October 6, 2024

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!

6. Head of the Charles Regatta (Cambridge) – October 18-20, 2024

Head over to Cambridge for the world-famous Head of the Charles Regatta. Cheer on the rowers, grab some tasty treats from food vendors, and enjoy the lively atmosphere along the Charles River.

7.) Kendall/MIT Open Space Fall Party (Cambridge) – October 5, 2024

The Kendall/MIT Open Space Fall Party is a celebration for friends and neighbors in Cambridge, MIT, and Kendall Square! Enjoy delicious food from local food trucks, live music by the Fly By Brass Band, and complimentary chai and hot cocoa while supplies last. Kids can dive into face painting and lawn games, making it a perfect day for the whole family.

8. Brookline Porchfest – September 28, 2024

If you’re looking for a unique music experience, Brookline Porchfest has you covered. Walk through the neighborhood and catch live performances from musicians playing right on their porches. It’s a fun, laid-back way to spend a fall afternoon.

9. Newton Harvest Fair – October 19-20, 2024

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.

10.) Bates School Pumpkin Fair (Wellesley) – October 5, 2024

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.

11. Pumpkin Decorating Party (Dover) – October 26, 2024

Looking for classic small-town fall vibes? Dover Days Fair is where you’ll find local crafts, a farmers’ market, live entertainment, and fun activities for kids. It’s a great spot to soak in the season’s charm.

13. Newtonville Village Day – September 29, 2024

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.

13.) HONK! Festival 2024 – Somerville (October 4-6, 2024)

Experience HONK! Festival 2024, a free three-day celebration of music and activism in Somerville! Kick off with a lantern parade on Friday, dance to over 30 brass bands on Saturday, and join a vibrant parade for local causes on Sunday. With a Day of Action and engaging discussions, HONK! Fest is a powerful celebration of community and change!

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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