Family-Friendly Fall and Halloween Events in the Berkshires

Berkshire spooky storytimes, trick-or-treat, pumpkin walks, halloween activities & more

We've spent some time gathering up Berkshire Fall Fun — and it's looking

Have an event to add? You can do so HERE. This calendar is continually being updated, so be sure to bookmark it and check back regularly.

This guide is being updated daily for Fall/Halloween 2025

Click here for a list of town-by-town trick or treat times.

Featured

Whitney's Pumpkin Fest 2024 (Through Oct. 26)

Fridays 1-5 p.m., Saturdays & Sundays 11 a.m.-5:30 p.m. (Weather permitting).

U-Pick Pumpkins, Haunted Corn Maze, and Dairy Bar will be open!

1775 State Road, Cheshire.

whitneysfarm.com

Ongoing

Naumkeag Incredible Pumpkin Show (Oct. 1-Oct. 31)

The Naumkeag pumpkins are back this year with more pumpkins, more fun, and an expanded schedule! Explore the gardens as they transform Naumkeag into a celebration of autumn with over 1,500 jack-o-lanterns, hundreds of mums, pumpkins and countless gourds – most of which were grown right at Naumkeag! Runs Wednesdays-Sundays, Oct. 1- Oct. 31. SEE HERE for tickets and to schedule a time. Tickets range in price $12-$25. 5 Prospect Hill Rd, Stockbridge.

Hoosac Valley Fall Foliage Train Rides (Through Oct. 19)

Hop a train for scenic fall foliage and a historic and informative hour-long roundtrip journey through the beautiful Hoosac Valley!
Saturdays & Sundays through Oct. 19. Departure Times: 11:30 a.m., 1:30 p.m., and 3:00 p.m. Advanced ticket purchase is required. Mark your calendar for the Halloween Trains on Oct. 25 and 26. 3 Hoosac St., Adams.

13 Nights at Jiminy Peak (September: 26th & 27th October: 3 & 4, 10, 11, 12; 17 & 18; 24 & 25; 30 & 31)

Unearth some terror this season at Jiminy Peak, where darkness closes in and demons come out at nightfall. Are you ready to dig up the hidden secrets buried in the mountain’s past? Perhaps. But you’ve been warned: Don’t get in over your head. *Recommended for ages 10 and up. 37 Corey Rd Hancock.

More Events — Click on Event for More Information

This guide is being updated daily for Fall/Halloween 2025

Ghost Tours at Ventfort Hall (Lenox) 🎃September 26, 2025

Fall Fun at Ioka (Hancock) 🎃September 27, 2025

44th Annual Apple Squeeze (Lenox) 🎃September 27, 2025

28th Annual County Fair (Hancock) 🎃September 27, 2025

Fall Family Fun Festival (Becket) 🎃September 27, 2025

Kids Ghost Tour (Lenox) 🎃October 3, 2025

Fall Foliage Children's Parade & Fair (North Adams) 🎃October 4, 2025

Fall Fun at Ioka (Hancock) 🎃October 4, 2025

Oktoberfest (Pittsfield) 🎃October 4, 2025

69th Annual Fall Foliage Parade (North Adams) 🎃October 5, 2025