23 Fun Fall Events In Massachusetts

Autumn in New England means stunning fall foliage, changing light, and gorgeous family photos. And, of course, awesome outdoor adventures featuring apples, pumpkins, corn mazes, cider, donuts, and more. September and October offer a plethora of fall festivals, activities, and events that celebrate the harvest season, plus a few that provide a wee bit of spooky fun guaranteed to start getting you into the Halloween spirit.

Limited-Run Events

1. September 16: 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)

2. September 22: Visit the bees, taste delicious honey-and-apple combinations, share stories and songs, and make apple crafts at this Apple Honey Harvest. (Lincoln)

3. September 23: 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)

4. September 23: Fluff Fest draws over 12,000 people to a madcap festival celebrating the 100th anniversary of the invention of Fluff. (Somerville)

5. September 23-24: Enjoy original handmade crafts by 48 local artisans, food trucks, live music, and more during the 7th Annual Craft Festival at Fruitlands. (Harvard)

6. September 30: The Berklee BeanTown Jazz Festival features world-class musicians, international food, and an instrument petting zoo staffed by Berklee professionals. (Boston)

7. October 6-8: 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)

8. October 7: It’s hayrides, PYO pumpkins, games, contests, live music, and more when the fields transform into fairgrounds at Verrill Farm’s Harvest Festival. (Concord)

9. October 8: Build a Sukkah, help with the Fall harvest, learn about honeybees, sing, tell stories, and press cider at Powisset Farm’s Sukkot Festival. (Dover)

10. October 8: Celebrate autumn in New England at the Fruitland Museum’s Harvest Festival. Learn about Native American winter preparations from seasons long ago, visit with local livestock, taste local produce, have your silhouette created by a local artist, and create your very own Farmer Hat or Shaker Bonnet. (Harvard)

11. October 8: Chestnut Hill Farm's 3rd Annual Harvest Festival features pumpkin carving and painting, a pie contest, goat milking, face painting, an open barnyard, food, live music, and much more. (Southborough)

12. October 14: Fall Foliage Fun Day kicks off the season with guided hikes, spectacular views, kite making, lawn games, cider donuts, s’mores, and more. (Andover and North Andover)

13. October 14-15: Live performances, pumpkin decorating, craft vendors, and amusement rides take over the streets at the Newton Harvest Fair. (Newton)

14. October 14-15: See who wins the scarecrow contest at Sturbridge’s 27th Annual Harvest Festival. Enjoy their mini food truck festival while browsing through the wares of over 50 local artisans and crafters. (Sturbridge)

15. October 14-15, 21-22, and 28-29: Smolak Farm offers a Not-So-Scary Monster Safari Hayride during the last three weeks in October. Participating children receive Halloween candy, an apple cider donut, and a sugar pumpkin to take home. Costumes encouraged. (North Andover)

16. October 19-22, 26-29: The Ecotarium offers its 14th Annual Great Pumpkin Fest. Celebrate the season with themed science programs, free planetarium shows, and more than 1,000 carved pumpkins. (Worcester)

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17. October 20: Floating pumpkins, luminaries, and a costume parade, along with stories, treats, drinks, and spooky fun make the Frog Pond Pumpkin Float a lovely way to spend an evening. (Boston)

18. October 21: Explore hay mazes, hay rides, farm animals, live owl programs, live music and more at the 37th Annual Daniel Webster Farm Day at the Daniel Webster Wildlife Sanctuary. (Marshfield)

19. October 21: Friendly newfies with small carts transport PYO pumpkins from patch to vehicle at Smolak Farm’s Newfoundland Dog Pumpkin Pull. (North Andover)

Recurring Events

20. Connors Farm offers a wide range of family activities each weekend throughout October, 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)

21. Smolak Farm offers a Children’s Festival each weekend in September and October with PYO pumpkins, hayrides, hay and corn mazes, face painting, a bouncy house, and many others children’s activities. (North Andover)

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

23. 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)

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Featured photo by Aaron Burden on Unsplash