Weekend Outlook: A Haunting Time
Check out the fun events happening this weekend in the Berkshire's including Halloween themed events and fall festivals.
Editor's Pick
The Vagabond Ball
The Colonial Theatre, Pittsfield
Friday, Oct. 17 at 7:30 p.m.
Enjoy a night of dancing and live music at the Colonial Theatre. Featuring artists Bella's Bartok, The Slambovian Circus of Dreams, and The Picky Bastards who will provide different types of music perfect for the fall season. Tickets are $30 each.
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 Train Ride, Adams
Oct. 11 thru 13; Departure Times: 11:30 a.m., 1:30 p.m. and 3 p.m.
Gaze at Berkshire County's fall foliage on Berkshire Scenic Railway Museum's Speedliner featuring the two classic Budd Rail diesel cars, New Haven 41 and Baltimore and Ohio 1960.
Tickets range from $13 to $28. More information here.
Naumkeag Pumpkin Show
Naumkeag, Stockbridge
Oct. 1 to 31 on Wednesdays through Sundays from 5 to 9 p.m.
More than 1,500 jack-o'-lanterns will grin back at you.
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.
Friday
The Vagabond Ball
The Colonial Theatre, Pittsfield
Time: 7:30 p.m.
Enjoy a night of dancing and live music at the Colonial Theatre. Featuring artists Bella's Bartok, The Slambovian Circus of Dreams, and The Picky Bastards who will bring you to your feet with all different types of music perfect for the holiday season. Tickets are $30 each.
More information and tickets here.
Saturday
Downtown Pittsfield Inc. its Alive: Kids Zone
St.Joseph's Church lawn, Pittsfield
Time: 10 a.m. to 1 p.m.
Kids are able to enjoy a bounce house, face painting, Halloween arts and crafts, giveaways, and more. Kids are encouraged to wear their Halloween costumes to enjoy a day of fun Halloween activities.
Downtown Pittsfield Inc. Its Alive: Night Circus
Dunham Mall, Pittsfield
Time: 3 to 6 p.m.
Bring the family and friends out to enjoy a variety of live music and performances hosted by Downtown Pittsfield Inc. Enjoy two fire performances by Jesse M. Thomas. Enjoy food and beverages from different businesses. Also enjoy a tarot reading by Emily Dunsay.
Downtown Pittsfield Inc. Its Alive: Teen Dance Party
Liberty Street, Pittsfield
Time: 7:30 to 9 p.m.
High School students can enjoy a night of dancing from a live DJ. Students are able to wear their Halloween costumes with no face masks if they want to. There will be a face painter who can do glitter and glow paint for free. There will be drinks for purchase from WANDER.
Open to current Berkshire County High School Students with their school ID only.
More information for all three of these events here
Downtown Bennington Harvest Festival
Main St, Bennington VT
Time: 10 a.m. to 5 p.m.
Bring the family to enjoy a free day of kids activities, live music, local vendors, and more.
More information here.
Berkshire County Walk to End Alzheimer's
Adams Visitor Center
Time: 8 a.m.
Join the walk or encourage those walking to end Alzheimer's this weekend.
More information here.
Murder Mystery: Midnight at the Masquerade
Milne Public Library, Williamstown
Time: 7 to 9 p.m.
Celebrate Halloween with a murder mystery at the library. Dress up to fit a character and determine who is the murderer. Enjoy adult beverages and snacks and solve the crime at hand.
More information here.
Clarksburg School's Annual Haunted Hayride
Clarksburg State Park, 1199 Middle Road
Time: 6 to 9 p.m.
Sunday
Shadow Puppetry Workshop with Sandglass Theater
27 Park Street, Adams
Time: 11 a.m.
Bring the kids to learn about shadow puppetry. Using differents lights and shadows you will learn how to to tell and create a story using shadows. Tickets are $15 each.
More information and tickets here.
Fall Festival Craft Fair
Berkshire Hills Country Club, Pittsfield
Time: 10 a.m. to 3 p.m.
Enjoy local crafters with unique handmade items to choose from.
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.
Lee
The Town Park
Saturdays: 10 a.m. to 2 p.m., through Oct. 11
The market offers locally grown produce, prepared foods, locally created arts and crafts, and herbal products. YogaLee offers free community yoga from 9:30 to 10:30 on the first Saturday of each month.
The market accepts SNAP, HIP, Senior Coupons, and WIC Coupons and also offers Market Match. More information 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 farmers market will set up on the south side of Main Street.
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