Family-Friendly Fall and Halloween Events in the Berkshires

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

By Berkshires Macaroni Kid September 19, 2023

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.


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. 


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) πŸŽƒSeptember 23, 2023

42nd Annual Apple Squeeze (Lenox) πŸŽƒSeptember 23, 2023

Fall Fest (Egremont) πŸŽƒSeptember 23, 2023

Hocus Pocus Movie Night (Cummington) πŸŽƒSeptember 23, 2023

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

Fall Fun at Ioka (Hancock) πŸŽƒ (Ongoing)

Fall Fun Weekends (Deerfield) πŸŽƒ(Ongoing)

Autumn Scavenger Hunt (Lanesborough)

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

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

Fall Family Discovery Hike (Hinsdale) πŸŽƒSeptember 30, 2023

13 Nights At Jiminy (Hancock) πŸŽƒ (Ongoing)

OktoberFest (Pittsfield) πŸŽƒOctober 1, 2023

67th Annual Fall Foliage Parade (North Adams) πŸŽƒOctober 1, 2023

66th Salisbury Fall Festival (Salisbury) πŸŽƒOctober 6, 2023

Kids Paint & Sip (Pittsfield) πŸŽƒOctober 6, 2023

Harvest Festival Craft Fair (Lenox) πŸŽƒOctober 7, 2023

Farmers Market Kid's Day (Lee) πŸŽƒOctober 7, 2023

BBG 89th Annual Harvest Festival (Stockbridge) πŸŽƒOctober 7, 2023

Beaver Pond Storytime & Nature Walk (Lenox)

Oktoberfest (Sandisfield) πŸŽƒOctober 8, 2023

Fall Harvest Fair (Williamstown) πŸŽƒOctober 8, 2023

RambleFest 2023 (Adams) πŸŽƒOctober 8, 2023 

55th Greylock Ramble (Adams) πŸŽƒOctober 9, 2023

Halloween Themed Cookie Decorating (Stockbridge) πŸŽƒ 

Fall Foliage Community Bike Ride (Pittsfield) πŸŽƒOctober 14, 2023

Purgatory Road (Dalton) πŸŽƒOctober 14, 2023

Harvest Fest in Downtown Bennington (Bennington) πŸŽƒOctober 14, 2023

Harvest Run, Kid's Fun Run (Pittsfield) πŸŽƒOctober 14, 2023

AutumnFest (Williamstown) πŸŽƒOctober 14, 2023

2nd Annual Best 'Tober Fest (Lanesborough) πŸŽƒOctober 14, 2023

Kids Halloween Party (North Adams) πŸŽƒOctober 14, 2023

Annual Haunted Hayride (Clarksburg) πŸŽƒOctober 14, 2023

STORYWALK® Keepunumuk: Weeâchumun's Thanksgiving Story (Lenox)

Medieval Faire (Lenox) πŸŽƒOctober 15, 2023

Truck Day (Great Barrington) πŸŽƒ

PJ Library Sukkot Pumpkin Fest (Cheshire)

Mini Pumpkin Painting (Stockbridge) πŸŽƒOctober 17, 2023

Spooky Barbie Makeover (North Adams) πŸŽƒOctober 18, 2023

Purgatory Road (Dalton) πŸŽƒ

It’s Alive! Block Party & Kids’ Zone! (Pittsfield) πŸŽƒ

Fireside Scary Stories (Sheffield) πŸŽƒ

HalloweenPalooza (North Adams) πŸŽƒOctober 22, 2023

Halloween Storytime and Craft (Stockbridge) πŸŽƒ

Ghost & Legends (North Adams) πŸŽƒOctober 25, 2023

Halloween Story Time and Trick or Treat (Lenox) πŸŽƒOctober 26, 2023

The Vanishing Hitchhiker: Spooky Stories & Urban Legends for Tweens & Teens (Lanesborough)

8th Annual Trunk-or-Treat (Sheffield) πŸŽƒOctober 27, 2023

nbCC's Downtown Trick or Treat (North Adams) πŸŽƒ

Halloween Family Fun Day (Great Barrington) πŸŽƒ

Downtown Trick or Treat (Lenox) πŸŽƒ

Trunk or Treat (Lenox) πŸŽƒ

Community Pumpkin Carve (Adams) πŸŽƒ

Pittsfield Halloween Parade (Pittsfield) πŸŽƒ

Ghost Tours at Ventfort Hall (Lenox) πŸŽƒOctober 27, 2023

Pumpkin Carving Spooktacular (Pittsfield) πŸŽƒ

Halloween at the Clark (Williamstown) πŸŽƒ

Halloween Family Walk (Dalton) πŸŽƒ

Pumpkin Walk (Adams) πŸŽƒ

Town of Otis Trunk or Treat (Otis) πŸŽƒ

Library Halloween Parade (Pittsfield) πŸŽƒ

Halloween Storytime and Craft (Stockbridge) πŸŽƒ