Massachusetts Fall Festivals: 15 best in 2025

Updated July 23, 2025  |   Published August 29, 2023 by Angela Talbot

Categories:  
• Local

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 15 picks for the best events in 2025. Mark your calendars and get ready for some fall fun!

Fall Festivals in Massachusetts

1. The Big E

West Springfield, MA | September 12 – 28, 2025

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 TLC, Train, and Foreigner, 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 18 & 29 – October 25 & 26, 2025

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 4, 2025

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 20 & 21, 2025

The Salem Food Truck & Craft Beer Festival will be hosting their 5^th annual event on the Salem Common this September. They have 40+ Food Trucks, Craft Beers, Artisan Market, Music, Lawn Games, and overall good fall vibes. 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 27, 2025

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

 

6. Charlton Old Home Day

Charlton, MA | August 31, 2025

Charlton Old Home Day takes place on Labor Day weekend every year to celebrate the end of summer and beginning of the fall harvest. You can find fun events, vendors, and entertainment for the whole family around the town common – and finish your night by watching the parade!

7. Harpoon Octoberfest

Boston, MA | October 3 & 4, 2025

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, a pretzel eating contest, and live music. Come back on Sunday, October 5^th 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 11 & 12, 2025

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. there will be 80+ craft vendors selling

 

9. What the Fluff?

Somerville, MA | September 20, 2025

Somerville’s “What the Fluff?” festival is a unique celebration in Union Square, honoring the invention of Marshmallow fluff.  They’re celebrating their 20th year of the festival in 2025.  This event is full of live music, delicious fluff meals, face painting, and family games. Fluff themed games and events: Marshmallow Toss, Fluff Jousting, Fluff Musical Chairs, Fluff Hairdos, and more.

 

10. Johnny Appleseed Arts & Culture Festival

Leominster, MA | September 20, 2025

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 over 200 vendor booths including Webster First’s Fitchburg branch!

 

11. Topsfield Fair

Topsfield, MA | October 3 – 13, 2025

The Topsfield Fair is a historic event dating back to 1820 when the Essex Agricultural Society had their first cattle show. Today, it’s a massive fall extravaganza including carnival rides, horse and oxen pulling, a largest pumpkin competition, parades, lots of good food, and more!

 

12. Saugus Founders Day

Saugus, MA | September 13, 2025

Founders Day is a day filled with live performances, vendors selling handmade crafts, inflatable obstacle courses, and more fun family activities. Pop on down to Town Hall to experience the festivities. Keep an eye out and you might spot a booth for our Saugus branch!

 

13. Dudley Grange Annual Apple Festival

Dudley, MA | October 4, 2025

There’s something for everyone at the Dudley Grange Apple Festival. Like delicious apple crisp for starters! Experience a petting zoo and  live musical performances while vendors sell their homemade goods on this exciting day at Dudley Grange. Don’t forget to stop and say hi if you see Webster First!

14. Sterling Fair

Sterling, MA | September 5, 6, and 7, 2025

The Sterling Fair is a beloved annual event celebrating community, agriculture, and family fun. Enjoy thrilling competitions like horse, oxen, and tractor pulls, along with livestock shows, carnival rides, delicious food, live entertainment, and a dazzling fireworks display. Perfect for all ages, it’s a weekend full of excitement and local charm!

 

15. Ashfield Fall Festival

Ashfield, MA | October 11 and 12, 2025

This event features exhibitor tables showcasing an array of handmade crafts, including jewelry, woodworks, blown glass, pottery, yarn, fabric creations, and more. Stroll down Main Street to explore a mouthwatering variety of food options, from St. John’s famous blueberry cobbler and the Boy Scouts’ apple cider donuts to the Hilltown Snowmobile Club’s kielbasa grinders, hearty corn chowder, sandwiches, and so much more!

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