Massachusetts Fall Festivals: 19 best in 2026

Updated August 11, 2026  |   Published August 29, 2023 by Angela Talbot | Reading Time: 6 minutes

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 19 picks for the best events in 2026. Mark your calendars and get ready for some fall fun!

Fall Festivals in Massachusetts

1. The Big E

West Springfield, MA | September 18 – October 4, 2026

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 Alice Cooper, Uncle Cracker, Ice Cube and Styx, 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 17 & 18 – October 24 & 25, 2026

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, daily magic and circus shows, and apple pie baking and eating contests. Wachusett’s SkyRide will also be open for the best views of the autumn leaves.

 

3. Douglas Oktoberfest

Douglas, MA | October 3, 2026

Fun for the whole family, Douglas Oktoberfest takes place every year on Main Street, right outside of 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 19 & 20, 2026

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 26, 2026

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. The Spencer Fair

Spencer, MA | September 4-7, 2026

The Spencer Fair has everything you would look for in a fall festival. From carnival rides, vendors, live music, and a demolition derby – to competitions like the giant pumpkin weigh-off, cattle show, tractor pulls, and much more! Don’t miss out on this huge event on the Spencer Fairgrounds all of Labor Day weekend.

 

7. Charlton Old Home Day

Charlton, MA | September 6, 2026

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!

8. Southbridge AutumnFest

Southbridge, MA | September 19, 2026

At the Town Common in Southbridge, MA you’ll find Southbridge AutumnFest, an annual celebration of the beginning of Autumn. Hosted by the Southrbridge Business Partnership, this event boasts vendors, live entertainment, delicious food and family fun.

 

9. Berkshire Botanical Gardens Harvest Festival

Stockbridge, MA | October 10 & 11, 2026

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 50 artisan craft vendors and regional food trucks this year.

 

10. What the Fluff?

Somerville, MA | September 19, 2026

Somerville’s “What the Fluff?” festival is a unique celebration in Union Square, honoring the invention of Marshmallow fluff.  Webster First is a sponsor of What the Fluff? in 2026!  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.

 

11. Johnny Appleseed Arts & Culture Festival

Leominster, MA | September 19, 2026

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 150 vendor booths including Webster First’s Fitchburg branch!

 

12. Topsfield Fair

Topsfield, MA | October 2 – 12, 2026

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!

 

13. Saugus Founders Day

Saugus, MA | September 12, 2026

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!

 

14. Dudley Grange Annual Apple Festival

Dudley, MA | October 3, 2026

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!

15. Sterling Fair

Sterling, MA | September 11-13, 2026

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!

 

16. Ashfield Fall Festival

Ashfield, MA | October 10 and 11, 2026

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!

 

17. North Quabbin Garlic & Arts Festival

Orange, MA | September 26 and 27, 2026

The North Quabbin Garlic & Arts Festival is held on an historic farm in North-Western Mass. At this family-friendly event you can expect craft vendors selling their wares, farmers selling farm products, main stage performances including music, spoken word poetry, and hula hooping, plus for the kids – face painting, temporary tattoos, a paint wall, and clay tables to make their own crafts! And as you would expect from the name, there will be plenty of local farms showcasing their garlic!

 

18. Touch of Magick’s Fall Psychic Fair

Uxbridge, MA | September 26 and 27, 2026

If you like witches and psychics, you’ll want to check out the Fall Psychic Fair at Touch of Magick. 30+ vendors set up to sell their unique products, including handmade goodies, oddities, jewelry, sun catchers, and more. Six psychics will offer 15-minute readings for $30 all day long on both days. Plus Reiki, Aura Photography, and so much more!

 

19. Apple Squeeze

Lenox, MA | September 26, 2026

All the way in Western Mass, the town of Lenox will be celebrating its 45th Apple Squeeze festival in Lenox Historic Village on Saturday, September 26th. At this event you can find an abundance of apple treats and pastries to taste throughout the day while you explore more than 100 artisan vendors selling handmade goods and support many of the local businesses who set up shop. There will also be live music and family activities, including a kids carnival, for everyone to enjoy at this free event.

 

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