Massachusetts Fall Festivals: 10 best in 2023

Updated March 22, 2024  |   Published August 29, 2023

It’s fall festival season in Massachusetts! Throughout September and October, you’ll find a variety of festivals to enjoy all over the state. Whether you want a family-friendly event complete with carnival rides or a food fest offering tasty treats and local craft beer, Massachusetts has it all.

Here, we’ve rounded up our 10 picks for the best events in 2023. Mark your calendars and get ready for some fall fun!


1. The Big E

West Springfield, MA | September 15 – October 1

The Big E is aptly named, as it’s the biggest and longest running festival in the state. The Big E has everything: vendors, farm animals, carnival rides, a farmers’ market, beer gardens, food trucks, and live entertainment from names like John Fogerty, Jimmy Eat World, and Third Eye Blind, just to name a few. Traffic can be heavy during weekends, so plan ahead with plenty of time to arrive and park.


2. Applefest at Wachusett Mountain

Princeton, MA | October 14-15, October 21-22

Wachusett Mountain has events happening every weekend in October. Two of those weekends consist of Applefest. During the season’s peak foliage period, you can enjoy craft vendors, a farmers’ market, live music, and apple pie baking and eating contests. Their SkyRide will also be open for the best views of the autumn leaves.


3. Douglas Oktoberfest

Douglas, MA | October 7

Fun for the whole family, Douglas Oktoberfest takes place every year on Main Street right outside our Douglas branch. This festival offers games, live music, a petting zoo, a beer garden, a car show, and more. Webster First is proud to sponsor the event for another year, so come check out our table if you’re there!


4. Salem Food Truck & Craft Beer Festival

Salem, MA |September 23-24

The Salem Food Truck & Craft Beer Festival will be hosting their 4th annual event on the Salem Common this September. While you’re there, there’s plenty of local history and art museums to check out after you finish chowing down!


5. Harvest Moon Festival, Onset Beach

Onset, MA | September 23

The Harvest Moon Festival is one of the biggest events in Onset. It offers attendees food trucks, vendors, face painting, live music, and more. Artists come to demonstrate their skills and the night ends with a grand fireworks display over the waters of Buzzards Bay.


6. Fabulous Fall Festival

Gardner, MA | September 30

The Fabulous Fall Festival is an annual event in Gardner during which the downtown area becomes an outdoor shopping and entertainment extravaganza. You can expect local businesses to open their doors and vendor tents to line the streets. Kids can enjoy inflatable slides, moon bounces, costumed characters, and games. Plus, the event offers live music. But that’s not all! Gardner Ale House will be hosting their Oktoberfest right down the street with more food, beer, and fun.


7. Harpoon Octoberfest

Boston, MA | September 29-30

In Boston’s Seaport district, Harpoon Brewery throws the biggest craft beer party that Bostonians can look forward to every year. In addition to Harpoon’s beers (including the aptly named “Octoberfest”), you can also find craft ciders and spiked seltzers. This festival will have vendors, food trucks, and live music. Come back on Sunday, October 30th for their “Dogtober Fest,” a festival for the dogs which will raise money for the Kenary Brain Tumor Research Fund at Dana-Farber Cancer Institute and MSPCA – Angell.


8. Berkshire Botanical Gardens Harvest Festival

Stockbridge, MA | October 7-8

The Berkshire Botanical Gardens Harvest Festival has been happening for over 80 years. This is a big event for families with lots of activities for kids to enjoy, including face painting, interactive music, a petting zoo, puppets, pony rides, and more. Beer gardens offer grown-ups something to enjoy as well.


9. What the Fluff?

Somerville, MA | September 23

Somerville’s “What the Fluff?” festival is a unique celebration in Union Square, honoring the invention of Marshmallow fluff. The theme of this year’s festival is Fluff at First Sight: Back on Track – a nod to previous years when the festival did not happen due to COVID-19 concerns. Now, they’re back on track with another event full of live music, delicious fluff meals, and family games.


10. Johnny Appleseed Arts & Culture Festival

Leominster, MA | September 23

John Chapman, famously known as “Johnny Appleseed” for introducing apple trees in states across the US and Canada, was born in Leominster, Massachusetts. Every year, the town holds the Johnny Appleseed Festival as a celebration of their history – and you bet that they indulge on apple-filled desserts! The downtown area becomes a hub for activities including live music, amazing food, and kids’ games. You will also find up to 230 vendor booths including Webster First’s Fitchburg branch!


Disclaimer: Webster First was not paid to endorse or evaluate the festivals or fairs mentioned in this post.