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 2023

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

Featured

Whitney's Pumpkin Fest 2023 (Through Oct. 31)

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 (Sept. 30-Oct. 29)

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, Sept. 30- Oct. 29. 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. 22)

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. 22nd. Departure Times: 11:00 a.m., 1:30 p.m., and 3:00 p.m. Advanced ticket purchase is required. Adults: $20, Children (4-14) $12. Mark your calendar for the Halloween Costume Train on 10/29. 3 Hoosac St., Adams.

Look Park Fall Weekends (Through Oct. 29)

The Haunted Train is back at Look Park on October 20-22 and October 27-29 from 4-8 pm each evening. New this year is Look Park Fall Weekend at Haunted Train, a fun fall festival during the second weekend of Haunted Train on October 28-29 from 2-8pm each day. The Fall Weekend will take place in the large ballfield next to the Train Station parking lot. At Fall Weekend (10/28-10/29) experience food trucks, fun crafts for kids featuring local vendors, live music, lawn games, a costume contest, face painting, full Adult Beverage Bar including tastings from your favorite local spots! Plus, firepits, picnic tables, open space, concessions and sweet treats and train rides throughout the day, including the Haunted Train in the evening! The festival is FREE to enter, with $10 standard park entry fee per vehicle. Additionally, Haunted Train tickets are $5 per ride, and cash/card will be acceptable by all vendors attending the Fall Weekend. Click here for more information. Look Park, 300 Main Street, Florence.

More Events — Click on Event for More Information

This guide is being updated daily for Fall/Halloween 2023

26th Annual County Fair (Hancock) 🎃September 23, 2023

42nd Annual Apple Squeeze (Lenox) 🎃September 23, 2023

Fall Fest (Egremont) 🎃September 23, 2023

Hocus Pocus Movie Night (Cummington) 🎃September 23, 2023

Whitney's Pumpkin Fest (Cheshire) 🎃 (Ongoing)

Fall Fun at Ioka (Hancock) 🎃 (Ongoing)

Fall Fun Weekends (Deerfield) 🎃(Ongoing)

Autumn Scavenger Hunt (Lanesborough)

Fall Foliage Festival Children’s Parade (North Adams) 🎃September 29, 2023

Fall Foliage Festival Children’s Road Race & Fair (North Adams) 🎃September 30, 2023