35 Fall Festivals in Massachusetts

Fall in New England means food, foliage, family, and fun. The changing light combines with bright Autumn colors to create an idyllic backdrop for awesome outdoor adventures and great family photos. This September, October, and November bring a bevy of festivals and events to help us all celebrate the season. Which means, of course, beautiful landscapes, apples and pumpkins aplenty, corn and hay mazes, fresh-pressed cider, and harvest feasts galore. We’ve put together this list of 35 fall festivals in Massachusetts to make your planning easy.

Limited-Run Fall Festivals

1. September 14: Visit the bees, taste delicious honey-and-apple combinations, share stories, sing songs, and make apple crafts at the Apple Honey Harvest. (Lincoln)

2. September 14-30: Check out The Big E calendar this year, and make plans to visit the largest agricultural event on the eastern seaboard. (West Springfield)

3. September 15: Verrill Farm celebrates local farming with tours, demonstrations, a petting zoo, apple dessert competition, live music, pony rides, hayrides, and more. (Concord)

4. September 15: Join Drumlin Farm’s Fall Harvest for cooking demonstrations, tastings, a tour of the fields, garden activities, and up-close encounters with animals who love to visit the garden. (Lincoln)

5. September 22: Visit with farm animals, climb aboard a tractor, paint your own pumpkin, learn about beekeeping and how to press apple cider, challenge your friends at the potato spoon, and make sure to enjoy an HKS Clydesdales wagon ride during the Annual Fall Festival at Weir River Farm. This event also offers food trucks, local brews, live music, old-fashioned lawn games, face painting, and ice cream. (Hingham)

6. September 22: Spend the afternoon kicking off a month-long Arts Across Medford Festival at the Mystic River Celebration. Enjoy live musical performances, local artisan crafts, great food, and fun activities for all ages. (Medford)

7. September 22: Fluff Fest draws over 12,000 people to a madcap festival celebrating the anniversary of Fluff’s invention. (Somerville)

8. September 22-23: Enjoy original handmade crafts by 40 local artisans, plus a food truck, live music, and more during the 8th Annual Craft Festival at Fruitlands. (Harvard)

9. September 23: The Sukkot in the City Potluck offers a free harvest celebration, as well as an opportunity to learn about the incredible network of community gardens in Boston. (Jamaica Plain)

10. September 29: The Berklee BeanTown Jazz Festival features world-class musicians, international food, and an instrument petting zoo staffed by Berklee professionals. (Boston)

11. September 30: Build a Sukkah, help with the Fall harvest, learn about honeybees, sing, tell stories, and press cider at Powisset Farm’s Sukkot Festival. (Dover)

12. September 30: Once again, the Needham Harvest Festival offers a fun fall celebration with a pumpkin patch, trolley rides, apple cider, and tons of activities for the whole family. (Needham)

13. October 5-7: Don’t miss the fun when Honk! comes to town. This annual three-day free festival brings brass bands from around the world together for a celebration of music, community, and activism. (Somerville)

14. October 6: It’s hayrides, PYO pumpkins, games, contests, live music, and more when the fields transform into fairgrounds at Verrill Farm’s Harvest Festival. (Concord)

15. October 6: Find local crafters, live music, children’s games and crafts, animals, trail walks, a duck derby, and more at the Stony Brook Wildlife Sanctuary’s Fall Fair. (Norfolk)

16. October 6-7: The Berkshire Botanical Garden Harvest Festival fills a 15-acre campus with children’s activities, pony and hayrides, games, live entertainment, over 100 regional artisan vendors, a farm market, tag and plant sales, and education offerings scheduled throughout the weekend. (Stockbridge)

17. October 6, 13: Follow the free Naumkeag Pumpkin Trail at night to meet nocturnal woodland creatures as they emerge from the local forest to share their stories. (Stockbridge)

18. October 7: Celebrate autumn in New England at the Fruitland Museum’s Harvest Festival. See livestock raised by local farms, find fresh food sources near you, taste local fruits and veggies, and enjoy crafts, live music, and other special programs throughout the day. (Harvard)

19. October 7: Enjoy Fall on the FARM. Take a hayride to meet up with the cattle herd, try your hand at squash bowling, play field games, check out a cider press, participate in pumpkin and face painting, then enjoy a pig roast, lemonade, and local brews. (Martha’s Vineyard)

20. October 7: Chestnut Hill Farm's 4th Annual Harvest Festival features pumpkin carving and painting, a farmer-judged pie-eating contest, goat milking, a photobooth for goat selfies, face painting, an open barnyard, fresh-pressed cider, food, live music, and much more. (Southborough)

21. October 8: Free Fall Family Fun Day kicks off the fall season with a nature-based scavenger hunt, spectacular views, kite making, lawn games, and more. (Andover and North Andover)

22. October 13: Join gardeners, family, and neighbors to celebrate the bounty of Dorchester’s largest community garden at the free annual Nightingale Harvest Potluck, which also includes food preservation demos and family activities. (Dorchester)

23. October 13: Sample s’mores and cider, play lawn games, take a pinetum tour, then leave for this free annual Fall Foliage Walk at Farandnear. (Shirley)

24. October 13-14: Bolton Orchards hosts Fall Craft and Fall Food Festivals, featuring local crafters, live music, fresh cider donuts, and other seasonal food. (Bolton)

25. October 13-14: Live performances, pumpkin decorating, craft vendors, and amusement rides take over the streets at the Newton Harvest Fair. (Newton)

26. October 13-14: See who wins the scarecrow contest at Sturbridge’s 29th Annual Harvest Festival. Enjoy their mini food truck festival while browsing through the wares of over 80 local artisans and crafters. (Sturbridge)

27. October 14: Powisset Farm launches the fall season with Harvest Fest, where you’ll find live music, hayrides, farm animals, demonstrations, contests, and a Vendor Village. Try navigating the hay maze, compete in field day activities like sack races and egg-on-a-spoon runs, participate in pumpkin decorating, ride a bicycle cider press, eat donuts on a string, or enter a competitive pie-eating contest. (Dover)

28. October 19: With a costume parade, magic tricks, floating pumpkins, and other luminaries, the annual Frog Pond Pumpkin Float is always a gorgeous evening. (Boston)

29. October 20: Explore hay mazes, hayrides, farm animals, live owl programs, live music, and more at the 38th Annual Daniel Webster Farm Day at the Daniel Webster Wildlife Sanctuary. (Marshfield)

30. November 17: Learn about wild turkeys, go for a hike, and scout for evidence of the autumn’s woodland wild harvest during Terrific Turkeys and Fall Harvest at Laughing Brook (Hampden)

31. November 23: The Felix Neck Wildlife Sanctuary Fall Festival draws a special crowd every year with its day-after-Thanksgiving hayrides, face painting, live music, and crafts for kids. (Vineyard Haven)

Recurring Fall Festival Events

32. Connors Farm offers a wide range of family activities each weekend throughout the fall, in addition to PYO apples and pumpkins. Make your way through the corn maze, play a round of pumpkin checkers, milk a cow, play pumpkin tetherball, pet the barnyard animals, and more. (Danvers)

33. Smolak Farm hosts a Fall Festival event each weekend in September and October with PYO apples, peaches, and plums, plus hayrides, face painting, a bouncy house, and many other children’s activities. (North Andover)

34. Each weekend in September and October brings PYO adventures, hayrides, a hay maze, and other kids’ activities at Shelburne Farm. (Stow)

35. Check out Frightful Fridays at Gore mansion, the perfect setting for an evening of spooky tales and haunted activities on Friday evenings in October. (Waltham)

35 fall festivals in Massachusetts

35 fall festivals in Massachusetts