Weekend Outlook: Halloween & Fall Events

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.

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.

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.

High Noon Band

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.

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.

 

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. 

McCann Committee Gets First Look at $17M Renovation Progress

By Jack GuerinoiBerkshires Staff
05:50AM / Monday, October 12, 2026

The project is in the home stretch with roofing and some windows and doors still to be installed. Superintendent James Brosnan also pointed above to HVAC improvements in the Guidance Office. 

NORTH ADAMS, Mass. — The McCann School Committee got a first look at the final stretch of a $17 million overhaul aimed at making the 64-year-old vocational school safer, quieter and more energy-efficient.

After a brief School Committee meeting Thursday, Superintendent James Brosnan led the members through the school, highlighting some of the changes made in the 64-year-old building.

"Just seeing this gives you a magnitude of the amount of work that goes on," he said.

The upgrades are being funded through the Massachusetts School Building Authority's Accelerated Repair Program and the Northern Berkshire Vocational School District's member towns.

Work was supposed to be completed before the start of the school year, but weather and the removal of materials caused a delay.

The tour was all indoors, and Brosnan told a disappointed committee that he was hesitant to take them onto the roof at night, but said the new roof is near 80 percent down.

"We have another 10, and 10 percent of that missing 20 is in the AVB [air and vapor barrier] and removal phase," Brosnan said. "That particular area is across the front, down the post-secondary ... we are going to pick up from guidance. So we have that plan going through next week. Fingers crossed, within two weeks we will have that piece down."

He said the roof has been built up and insulated for more efficiency.