• September 8, 2022
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15 Fall Festivals in Massachusetts to Attend in 2022

September 8, 2022

The first official day of autumn this year is September 22, but the festivals to kick off the fall season start well before that. We did our research to find 15 festivals happening throughout Massachusetts this September and October where you can enjoy attractions like live music, vendors, food trucks, competitions, and more. So get your calendar ready and read on!


1. The Big E

Sep. 16 – Oct. 2, 2022 | Springfield, MA

The Big E is by far the biggest and longest fall festival in Massachusetts. It has vendors, carnival rides, food trucks, beer gardens, farm animals, circus animals, parades, competitions, and lots of musical performances – some of which are free to attend with your entry ticket. This year on the Big E Arena stage you can purchase tickets to performances from names like Nelly, Lynyrd Skynyrd, G-Eazy, and the Dropkick Murphys, just to name a few.

Credit: The Big E on twitter


2. Douglas Oktoberfest

Oct. 1 | Douglas, MA

Douglas Oktoberfest is an annual festival on Douglas’s Main Street that grows bigger every year. Webster First is a proud sponsor of this event, which has vendors, crafts, food, beer gardens, a car show, a petting zoo, and competitive events like races. It’s fun for the whole family.


3. Salem Food Truck & Craft Beer Festival

Sep. 24 – 25 | Salem, MA

Foodies, take notice! For two days some of the most popular food trucks in the area, as well as dozens of regional and national breweries, will be dishing out delicious food and craft beer. The Salem Food Truck & Craft Beer Festival will be happening on the Salem Commons.


4. Johnny Appleseed Arts & Culture Festival

Sep. 24 | Leominster, MA

The annual Johnny Appleseed Arts & Culture Festival is named, of course, after the famous Johnny Appleseed who was born in Leominster on September 26, 1774. This year’s event will feature live music all day, apple crisp, food trucks, vendors, and a kid’s party. Team members from our Fitchburg branch will be participating, so stop by and say hello while you’re there. Plus, admission and parking are both free!

Credit: Johnny Appleseed Arts & Culture Facebook page


5. Townsend Historical Society Fall Arts and Crafts Fair

Sep. 17 -18 | Townsend, MA

The Townsend Historical Society Fall Arts and Crafts Fair takes place on the historic town common in Townsend. Vendors sell their handmade wares such as artwork, photography, wood carvings, glass, leather, jewelry, clothes, and more! Make sure you bring cash to take home any treasures you find. (Helpful hint: Webster First members enjoy fee-free withdrawals from Webster First ATMs or ATMs in the SUM or CO-OP Networks.)


6. Old Deerfield Fall Arts and Crafts Festival

Sep. 17 – 18 | Deerfield, MA

Similar to the Townsend Arts and Crafts Fair, the Old Deerfield Fall Arts and Crafts Festival is also great for art lovers. Happening at Memorial Hall museum, this fair features more than 180 juried exhibitors from 16 states displaying and selling crafts of all media. Complete with a museum tour, music, a food court, and specialty food sampling.


7. Marlborough Food Truck & Arts Festival

Sep. 18 | Marlborough, MA

The Marlborough Food Truck & Arts Festival caters to foodies and art lovers alike. Happening in downtown Marlborough near city hall; this event will have food, artists, crafters, a beer garden, live music, and more.


8. Harvest Moon Festival

Sep. 24 | Onset, MA

The Harvest Moon Festival takes place by the ocean at Bay View Park in Onset. It has vendors, a flea market, food trucks, an antique car show, live music, and a fireworks display over the water at dusk! You can also participate in contests for the best chili, chowder, and stuffies (New England’s word for stuffed clams).


9. Wellfleet Oysterfest

Oct. 16 | Wellfleet, MA

The Wellfleet Oysterfest is an annual event in Cape Cod that is put on by the non-profit organization SPAT (Shellfish Promotion and Tasting). Oysterfest is visited by thousands each year. It’s run by volunteers and generous donations from local businesses. All proceeds go to support the local aquaculture and shellfish industries. If you love oysters or shellfish, this is definitely the place for you. While you’re chowing down, also enjoy music, art, local beer and wine, and watch the shucking competition!

Credit: tripadvisor


10. Duxbury Oktoberfest

Sep. 24 | Duxbury, MA

Duxbury Oktoberfest, also known as the Duxbury Food and Wine Festival, is one of the pricier events on the list. For this 21+ festival, tickets are $60 per person or $95 per couple. With your admission, you’ll be served wine, beer, and appetizers for tasting. Then choose your dinner from a full menu of German and American food, and have fun dancing until the night ends!


11. North Quabbin Garlic and Arts Festival

Oct. 1 – 2 | Orange, MA

The North Quabbin Garlic and Arts Festival at Fosters Farm in Orange is perfect for garlic lovers. With a tagline stating “The Festival That Stinks!” you’re sure to eat a lot of garlic infused cuisine. You’ll also be able to watch chef demos to learn the art of cooking with garlic. According to their website the event will also have amazing art, musical performances, fun activities for families, and a…portal to the future??


12. Revere Fall Festival

Sep. 24 | Revere, MA

The Revere Fall Festival is right by the ocean on Broadway in the city of Revere. Here you will find local vendors, live music, a beer garden, a family zone, and more!


13. Berkshire Botanical Gardens Harvest Festival

Oct. 8 – 9 | Stockbridge, MA

The annual Berkshire Botanical Gardens Harvest Festival celebrates autumn, and in 2022 will feature two days of live music, vendors, local artisan food, a plant sale, a farmer’s market, pony rides, hay rides, a haunted house, classes and workshops, and even more that hasn’t been announced yet!

Credit: Spectrum News


14. Newton Harvest Fair

Oct. 15 – 16 | Newton, MA

Newton Harvest Fair is a 2-day event with carnival rides, food trucks, live music, and vendors. However, Saturday will only have kiddie carnival rides and games. Sunday will be the day for vendors and live music, so plan your trip accordingly.


15. Lowell Halloween Craft Fair

Oct. 29 | Lowell, MA

Last but not least, the Lowell Halloween Craft Fair at Shedd Park Pavilion is a great event for kids. The admission is free and there will be over 40 local crafters and vendors there. Kids can dress up in their Halloween costumes and trick-or-treat at the vendor booths.



Webster First is proud to be a sponsor for the Douglas Oktoberfest and participant in the Johnny Appleseed Arts & Culture Festival. Although we have made every effort to provide the most accurate information possible, we assume no liability for any errors or inaccuracies, and are not affiliated with the organization or management of the events featured here.