Weekend Outlook: Pumpkins and Fall EventsBy Breanna Steele, iBerkshires Staff
12:27PM / Thursday, September 25, 2025 | |
Check out the events around the county this weekend including pumpkins, festivals, and more to enjoy.
Editor's Pick
Festival Latino of the Berkshires 2025
Great Barrington Town Hall
Time: 2 to 6 p.m.
Enjoy a parade, crafts, food, and dance celebrating Hispanic heritage behind Town Hall at Green Park and Saint James Place. Free salsa lessons and a dance social will be held at Mahaiwe Performing Arts Center..
More information here.
Multiple Days
The Big E
Eastern States Exposition, Springfield
Time: Sept. 15 to Oct. 1
New England's biggest fair runs through the end of the month. The fair features goods from all six New England states, specialty days, crafts, demonstrations, activities, agriculture, horse shows, and more.
Tickets range from $20 and $12 a day to full passes and group admissions. Special performances priced separately.
More information here.
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, corn maze, games, petting zoo, and more.
More information here.
Friday
History of Constellations and Stargazing
30 Rockwell Road, Lanesborough
Time: 7 to 10 p.m.
Hear from astronomer Bob Donahue about the stars and constellations and learn how historical events have brought the list of constellations we have today. Make sure to bring binoculars and a flashlight. Held at the Mount Greylock State Reservation Visitors Center.
More information here.
Tourists, North Adams
Time: 7 p.m.
Married couple Crystal and Pete Damore and award-winning folk music duo will "Sing for Your Slumber" in lodge at Tourists resort.
Free and open to the public; refreshments available for purchase. More information here.
Saturday
Brightoberfest 2025
Bright Ideas Brewing, North Adams
Time: noon
Bright Ideas on the Massachusetts Museum of Contemporary Art campus will have authentic German music by HofBrauhaus. Buy a stein and enjoy the music.
Fall Foliage Train Rides
Hoosac Valley Train Ride, Adams
Departure Times: 11:30, 1:30, 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.
Free Ride Day at Berkshire Carousel
50 Center St., Pittsfield
Time: noon to 5 p.m.
Hill Engineers, Architects and Planners is sponsoring a free ride day on the carousel. Take a spin on one of the hand-carved horses and animal with your friends and family.
More information here.
Sunday
Bill Lewis Memorial Fishing Derby and Oktoberfest Picnic
Farnam's Causeway, Cheshire
Time: 7 a.m. to 1 p.m., 1:30 to 5 p.m.
The fourth annual Bill Lewis Memorial fishing derby on Cheshire Lake offers prizes for adults and youth. After the awards ceremony, enjoy an Oktoberfest picnic on Farnam's Causeway with food, raffles, music, and more.
More information here.
North Adams Boxcar Derby & BBQ
Main Street, North Adams
Time: 1 to 5 p.m.
Get ready to race your boxcars this Sunday! Enjoy a day of races, prizes, and more. Don't forget your helmet and be sure to grab some BBQ from North Adams' own police and firefighters, Grazie and Horn of Plenty Catering. Sponsored by the city's Office of Tourism. Be aware that Main Street will be closed during this time so plan accordingly.
More information here.
Autumnal Tea Party
76 Spring St., Williamstown
Time: Noon
Boba and Tea lounge is offering a curated menu of sandwiches, sweets, and tea. Tickets are $30 per person.
More information and tickets here.
Riverwalk
Eclipse Mill, North Adams
Time: 4 to 6:30 p.m.
Hoosic River Revival holds the third in its riverwalk series, starting at 230 Union St. and ending at parking lot on Holden Street behind the Big Y with food, art-making, ecology and community. Pick up a sketchbook at the mill.
Free and open to the public; more information here.
Farmers Markets
Great Barrington Farmers Market
18 Church St.
Saturday: 9 a.m. to 1 p.m.
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 Farmers Market
The Town Park
Saturday: 10 a.m. to 2 p.m.
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.
Lenox Farmers Market
St. Ann's Church
Friday: 11 to 3.
This market is open every Friday through Sept. 12 and features fresh produce, pastries, cheeses, and more.
More information here.
New Marlborough Farmers Market
Village Green
Sunday: 10 a.m. to 1 p.m.
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 Farmers Market
Main Street
Saturday: 9 a.m. to 1 p.m.
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. More information here.
Pittsfield Farmers Market
Pittsfield Common
Saturday, 9 a.m. until 1 p.m.
Roots Rising, the region's first teen-run market, will hold an indoor farmers market this Saturday. The event will feature live music, chef demos, workshops, children's activities, and more. More information here.
Sheffield Farmers Market
125 Main St.
Fridays, 3 to 6 p.m.
The market features healthy food and products from a variety of local vendors, aiming to nourish the community by supporting "local small farms, land, bees, and economy."
More information here.
Williamstown Farmers Market
Spring Street
Saturday, 9 a.m. to 1 p.m.
The market features a diverse range of local food and artisan vendors, along with local services and live music. More information here.
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