Massachusetts Fall Festivals: 13 best in 2024

Updated September 9, 2024  |   Published August 29, 2023

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 13 picks for the best events in 2024. Mark your calendars and get ready for some fall fun!

Fall Festivals in Massachusetts

1. The Big E

West Springfield, MA | September 13 – 29, 2024

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 Ludacris, Umphrey’s McGee, and Public Enemy, 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 19 & 20 – October 26 & 27, 2024

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 5, 2024

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 21 & 22, 2024

The Salem Food Truck & Craft Beer Festival will be hosting their 5^th 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 28, 2024

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 | September 1, 2024

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 4 & 5, 2024

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 6^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 12 & 13, 2024

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 21, 2024

Somerville’s “What the Fluff?” festival is a unique celebration in Union Square, honoring the invention of Marshmallow fluff.  They’re back with another event full of live music, delicious fluff meals, face painting, and family games.

 

10. Johnny Appleseed Arts & Culture Festival

Leominster, MA | September 14, 2024

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!

 

11. Topsfield Fair

Topsfield, MA | October 4 – 14, 2024

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 14, 2024

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 5, 2024

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!

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