Weekend Outlook: Halloween & Fall EventsBy Breanna Steele, iBerkshires Staff
12:15PM / Thursday, October 23, 2025 | |
Check out the Halloween and fall events happening this weekend throughout Berkshire County. A list of trick-or-treat hours and events can also be found here.
Editor's Pick
Pittsfield Halloween Parade
The Halloween week kicks of at 7 p.m. on Friday as Pittsfield hosts the "Haunted Hometown Spooktacular" parade. It will proceed down Tyler Street and across the Woodlawn Avenue Bridge and will include city departments, organizations and residents walking the parade and showing off costumes from parades past.
More information here.
Multiple Days
Pumpkinfest 2025
Whitney's Farm & Market, Cheshire
Every Friday through Sunday until Halloween
Join the festivities at Whitney's Farm on Route 8 with hay rides, games, glitter tattoos, and more. Kids can venture off into the corn maze or make a new acquaintance at the petting zoo that includes a mini pony, baby goats, sheep, and a peacock.
Children can also scale different structures in the play yard and once they have worked up an appetite, pick up lunch in the farm market. Whitney's is located at 1775 South State Road in Cheshire and is open from 9 a.m. to 6 p.m. daily. More information here.
13 Nights Returns
Jiminy Peak Mountain Resort, Hancock
The terrifying favorite returns to provide a fright-filled weekend to participants brave enough to enter the haunted house.
Take a group of friends to participate in "13 Nights at Jiminy" every Friday through Sunday from 6:30 until 10:30 p.m. through the month of October.
The age recommendation is 10 and older. Tickets are $29.
You can also ride through the darkness with the resort's Mountain Coaster for $16; The Scream and Scare Package includes one trip through "13 Nights" and two rides on the coaster for $49.
The Christiansen's Tavern will be open to purchase drinks, dinner, or a snack Friday and Saturday.
More information and tickets here.
Fall Foliage Train Rides
Hoosac Valley Trains, Adams
Oct. 25 & 26; Departure times: 1:30 p.m. and 3 p.m.
Family friendly Halloween-themed ride on the Berkshire Scenic Railway Museum's Speedliner
Tickets range from $14 to $30. More information here.
Naumkeag Pumpkin Show
Naumkeag, Stockbridge
Oct. 1 to 31; Wednesdays through Sundays from 5 to 9 p.m.
More than 1,500 jack-o'-lanterns will grin back at you on the grounds of the Naumkeag estate.
Pumpkins, mums, and gourds decorate the mansion's grounds and are sure to be a spectacle the entire family will enjoy. Hot cider and fall treats will be available for sale on-site. Tickets can be purchased here.
City of the Dead
203 Wahconah St., Pittsfield Cemetery
Runs through Oct. 30
Enjoy a spooky lamplight tour of the Pittsfield Cemetery in preparation for the creepy holiday. You will learn about the stories of those who are in the cemetery. The tours start at 6 p.m. and cost $10.
More information here.
End of Autumn Fall Festival
Greylock Glen, 165 Gould Road, Adams
Time: 10 to 6, Saturday and Sunday
Head to the Greylock Glen Outdoor Center for live music (1 to 3), food, and bar service. Bring your yoga mat (11 a.m.), hiking boots (guided tours at 10 and 2), and your appetite for what looks like another beautiful weekend in the Berkshires.
On Saturday, the Thunderbolt Ski Runners will have a trail work from 9 to 1 and the Northern Berkshire Astronomical Society will offer a lecture and stargazing from 6 to 8 p.m.
Friday
North Adams Haunted House
Mohawk Theater, North Adams
Time: 6 to 10 p.m.
The North Adams Strong Communities Haunted House is back with the theme "Haunted Circus." The interior of the vacant Mohawk Theater will dressed up to terrorize those brave enough to walk through it. Make sure you get your trick-or-treating in first during Northern Berkshire Community Coalition's downtown event with participating merchants.
More information here.
Trunk or Treat
65 Walker St., Lenox
Time: 5:30 p.m.
The Lenox Community Center is hosting a Trunk-or-Treat, rain or shine.
More information here.
Kids Ghost Tour at the Mount
2 Plunkett St., Lenox
Time: 6 to 8 p.m.
Bring your kids for a 75-minute tour of The Mount to learn about the haunted stories that have taken place there. Geared for children ages 6 to 12, who must be accompanied by an adult. Costs $10 to $20.
Tickets and more information here.
All Level, All Request Open Dance Night
399 1/2 Main S., Dalton
Time: 6 to 10 p.m.
Line Dancing with Tina is hosting a Halloween dance night at the Hall in the Union Block. Bring your dancing shoes and dance the night away.
More information here.
Saturday
Berkshire Humane Choose Your Subaru Raffle
Berkshire Humane Society, Pittsfield
Time: 8:30 a.m. to 2 p.m.
Join Berkshire Humane Society as its host the annual Subaru raffle fundraiser with Haddad Subaru. There will be a free microchip clinic from 8:30 to 10 a.m. followed by lawn games and vendors and will end with the raffle drawings at 1 p.m.
More information here.
Future Lab[s] Closing Reception
43 Eagle St., North Adams
Time: 6 p.m.
This closing reception is also a Halloween party so dress up for the final exhibition of works by Ricky Darell Barton and Alicia Canary.
High Lawn Halloween
High Lawn Farm, Lee
Time: 11 a.m. to 2 p.m.
High Lawn Farm offers a family Halloween event. Bring the kids in their costumes for a contest that starts at 12:30 p.m. There will also be pumpkin carving and painting, raffles, games, food, and more.
More information here.
Adams Theater, Park Street
Time: 7:30 p.m.
High Noon is a Southern rock tribute band, playing classics from Lynyrd Skynyrd, the Allman Brothers Band, Molly Hatchet and more.
Tickets and more information here.
Harvest and Halloween Party
175 Wendell Ave, Pittsfield
Time: 4 p.m.
The Unitarian Universalist Church of Pittsfield is hosting a harvest and Halloween party.
More information here.
Boosquet Halloween Party
101 Dan Fox Drive, Pittsfield
Time: 7 to 11 p.m.
Bosquet, in conjunction with Berkshire Roots, is hosting its second annual 21-plus Halloween Bash. There will be music, dancing, food, drinks, and more. Tickets are $39.
Tickets and more information here.
Eerie Ecology: A Spooky Nature Hike
The Boulders, Dalton
Time: 4:30 to 5:30 p.m.
Berkshire Natural Resources Council leads an exploration of the spooky side of nature in this family friendly guided walk. Costumes for all are encouraged.
The Boulders is located on Gulf Road; participation is limited so reserve at chood@bnrc.org. More information here.
Sunday
Halloween Scavenger Hunt and Open Farm Day
262 Loop Road, Savoy
Time: 1 to 3 p.m.
Visit Second Chance Stables horse rescue and wear your costume for a Halloween scavenger hunt on the farm. If you don't have a costume there will be face painting for you. There will also be snacks and drinks and a raffle.
More information here.
Rainbow Tea Dance
5 Eagle St., North Adams
Time: 4:30 to 7:30 p.m.
Steeple City Social is hosting its fourth tea dance with DJ PRL. Have fun socializing, dancing, and a drink while listening to great music.
More information here.
Trick or Treat at the Springs Motel
94 Route 7, New Ashford
Time: 2 to 4 p.m.
Celebrate Halloween with free games, snacks, and drinks. All ages and pets are welcome to dress up and have a good time. RSVP to trick-or-treat at the motel.
More information here.
Farmers Markets
Great Barrington
18 Church St.
Saturday: 9 a.m. to 1 p.m., through Nov. 8
The market is open every Saturday. Every week, locally grown food, flowers, and plants will be available, along with other local vendors. The market accepts and offers doubling SNAP, HIP, WIC, and Senior market coupons. More information is here.
New Marlborough
Village Green
Sunday: 10 a.m. to 1 p.m., until weather turns
The market has local vendors that offer a variety of goods from produce, eggs, baked goods, jams, hand-knit items, maple syrup, and more. More information here.
North Adams
Main Street
Saturdays: 9 a.m. to 1 p.m., through Oct. 25
The south side of Main Street from American Legion Drive will be closed to make room for the city's weekly farmers market, which will kick off this Saturday. Explore downtown North Adams and discover local businesses and fresh produce from local farms.
Williamstown
Spring Street
Saturday, 9 a.m. to 1 p.m., through Nov. 1
The market features a diverse range of local food and artisan vendors, along with local services and live music. More information here. | 
