20 Fall Festivals + Harvest Events in Massachusetts

As we head into yet another pandemic school year, autumn feels fraught. Kids head back to classrooms while we continue to keep our circle tight, our faces masked, and our choices cautious. I’ll exhale a little when my younger child gets vaccinated, but in the meantime, outdoor fun is key.

Thankfully, Fall brings everything I love best about New England.  Nothing beats the changing light as it combines with bright Autumn colors and clear, crisp air. Equally awesome? Apple cider donuts.

Many beloved fall festivals and events return from their 2020 hiatus to help us all celebrate the season. If you’re craving scenic landscapes, apples, honey, pumpkins aplenty, corn and hay mazes, fresh-pressed cider, and delicious harvest eats, we’ve got you covered with this list of 20 Fall Festivals + Harvest Events in Massachusetts.

Limited Run Events

1. Now-September 6: Wander through fields of flowers, cut your own sunflowers, and snap the perfect family pic at Verrill Farm. Selfies, Sunflowers, and Bouquets benefits the Emerson Hospital Pediatrics Unit. (Concord)

2. September 3-6: Appleton Farms hosts a Labor Day Weekend Food Truck Takeover. (Hamilton & Ipswich)

3. September 2 & 9: Sunset Picnics at Weir Farm feature local breweries, food trucks, and live music. Greet Ruby the llama and Nutmeg the pony, explore an art installation, and enjoy the best view on the South Shore. (Hingham)

4. September 4: A Day of Apples and Art offers food trucks, cider tasting, apple vendors, giveaways, scavenger hunts, art lessons, wagon rides, live music, and more. (Leominster)

5. September 17-October 3: Check out The Big E calendar this year and make plans to visit the largest agricultural event on the eastern seaboard. (West Springfield)

6. September 18: Family Farm Day at Verrill Farm means lots of games to play, tractors to touch, and delicious food to eat. (Concord)

7. September 18: Southbridge AutumnFest is back with food, crafters, live entertainment, local brews, and more. (Southbridge)

8. September 19: Don’t miss the 11th Annual Boston Local Food Festival. (Boston)

9. September 22-26: The Fluff festival returns with Sweet 16: Onward & Fluffward! Fluff enthusiasts will swoon as scores of local businesses open their patios for a safe yet scrumptiously sticky soiree unlike ever before. (Somerville)

10. September 25: With stunning views of the Boston skyline and harbor for a backdrop, Sabores de Nuestra Cultura: Family Festival is not to be missed. Celebrate food, culture, and family at Piers Park in East Boston with free treats, music, games, and creative crafts. (Boston)

11. September 25: Cider, apple pie, fire engines, wagon rides, face painting, live music, and of course, PYO apple picking await attendees at Cook’s Farm Applefest. (Brimfield)

12. September 25: The Mystic River Celebration returns with live musical performances, local artisan crafts, great food, a Knucklebones play area, and fun activities for all ages. (Medford)

13. October 9-10: The Berkshire Botanical Garden Harvest Festival fills two days with live music, fresh local food, a farmer's market, regional vendors, pony and hay rides, haunted house, and a hay jump, plus a few extra surprises. (Stockbridge)

14. October 15: With food, floating pumpkins, luminaries, and fun family activities, the annual Frog Pond Pumpkin Float is always a gorgeous evening. (Boston)

15. October 16: Make way to Farm Day at Waltham Fields Community Farm, a free annual festival celebrating locally grown food with hands-on farm activities, educational demonstrations, live music, a pick-your-own carrot patch, field tours, kids games, and more. (Waltham)

16. October TBD: Honk! returns with its celebration of music, community and activism -- final dates and details to be announced very soon. (Somerville)

Recurring Events

17. Weekends, September 3-26: Smolak Farm hosts a Fall Festival each weekend in September with cider donuts, PYO apples and pumpkins, themed hayrides, carnival attractions, face painting, a bouncy house, and many other children’s activities. (North Andover)

18. Weekends, September 28-October 24: Head to the Krochmal Farms Pumpkin Festival for horse-drawn hay rides, pony rides, a corn maze, animal exhibits, and PYO pumpkins. (Tewksbury)

19. Sundays, September 5-26: Garden Games at Long Hill has cornhole, giant jenga, and croquet every weekend in September. (Beverly)

20. Saturdays, September 18-October 30: The Fruitlands Annual Craft Festival has been reimagined this fall, with Saturday Artisan Markets running each Saturday for 6 weeks. (Harvard)

35 fall festivals in Massachusetts