Weekend Outlook: Lenox Apple Squeeze and More
It might look to be a rainy first weekend of fall, but there's plenty to do around the Berkshires.
Editor's Pick
Lenox Apple Squeeze
Downtown Lenox
Saturday, Sept. 26, 10 a.m.-5 p.m.
The 45th edition of Lenox's signature fall festival features more than 100 artisan and food vendors, live music, family activities, and a full street fair experience in downtown Lenox.
The festival is free to attend and will include a day of family fun with music, food and a kids carnival, as well as musical performances throughout downtown.
More information here.
Multiple Days
Eastern States Exposition
West Springfield
Through Oct. 4
The Big E is the region's biggest fair with live entertainment, a midway, circus, exhibits, parades, booths, food, agricultural competitions, and presentations by each of the New England states.
Tickets and information here.
Friday
Fall Migration for Beginning Birders
Pleasant Valley Wildlife Sanctuary, Lenox
7-8:30 a.m.
This beginner-friendly walk focuses on bird-finding tips, simple identification cues, and observing bird behavior. The Pike's Pond Loop — a mostly flat trail with accessible features — offers a beautiful scenic view of both the pond and Yokun Ridge in the distance.
Registration and information here.
American Stories Curator Talks: Service and Sacrifice
Norman Rockwell Museum, Stockbridge
9:30 a.m.
Chief Curator Stephanie Haboush Plunkett will describe how during times of war artists and illustrators have worked as reporters, makers of propaganda, and mythmakers. This session will consider the ethical responsibilities of artists, including Norman Rockwell and J.C. Leyendecker, involved in wartime image production and will pose questions about memory, accountability, and the relevance of wartime imagery in our society.
Tickets and information here.
What's The Tea @ WCMA
Williams College Museum of Art, Williamstown
4-5:30 p.m.
Stop by the museum between 4 and 5:30 to learn about what's happening at WCMA this year. Start off in the lounge with a cup of tea before heading into the galleries for a peek at Object Lab, where you will see works of art classes will be studying this fall. Then make your way upstairs to get a behind-the-scenes look of how the museum is preparing for its new home, opening in 2027. Free and open to all.
More information here.
'Be Good!' with Paulette
The Foundry, West Stockbridge
7:30 p.m.
Hot off of an international tour, certified clown Daniel Maseda brings well-mannered idiot Paulette to the Berkshires for the very second time with this fan-favorite show that never plays out the same way twice. A good night for anyone who wants to scream at a polite person.
Tickets and information here.
Friday Karaoke
Dalton American Legion
6 p.m.
More information here.
Saturday
Harvest Run and Community Fun 2026
Paterson Field House, Berkshire Community College, Pittsfield
10 a.m.
The event includes a Community 5K Trail Run; a free Kids 1-mile Fun Run; a cook-off competition with plenty of delicious samples; a health and wellness fair, including massage, blood pressure checks and more; kids activities, games, and craft table; and a costume contest with the theme "Botanical Gardens" with awards.
All proceeds will benefit the BCC Nursing and Allied Health programs and students
More information here.
Berkshire County Buddy Walk
Craneville Elementary School, Dalton
10:30 a.m.
Hosted by Berkshire County Arc and the Berkshire County Arc Down Syndrome Family Group, the 20th annual edition of this one-mile walk starts and ends at Craneville Elementary School, where there will be lunch, raffle prizes, music and other activities. The walk will be held rain or shine.
More information here.
Author Talk
Lee Library
Noon
Local author Lara Tupper will discuss her book "Off Island" at the Lee Library. "Off Island" combines the painter's perception of the visual world with the sensuality and coarseness of the physical world. The event is free. Registration is recommended but not required.
More information here.
Queer Crafting
Wander Café, Pittsfield
12:30-2 p.m.
Knitters, crocheters, other crafters and beyond are welcome to join us to meet with other LGBTQ+ friends old and new for a twice-a-month craft and social time. Want to draw for an hour and a half, drink tea and chat? How about learning to knit? Need a time to finish up that project-in-process? All ages are welcome.
More information here.
Chili & Cornbread Night
Blackinton Union Church, North Adams
4:30-6:30 p.m.
Come enjoy a warm meal and a night of food, fellowship, and community. Dinner includes a bowl of chili, cornbread, a cookie, and a drink. Buttered noodles option available for kids. There will also be a bake sale.
More information here.
Harvest & Rust
Stationery Factory, Dalton
8 p.m.
Widely regarded as one of the premier Neil Young tribute bands in the Northeast USA, Harvest & Rust is celebrated for its stirring, deeply authentic performances. Each show is a thoughtfully curated journey through Young's remarkable catalog, drawing from his solo career as well as his work with Buffalo Springfield and Crosby, Stills, Nash & Young.
Tickets and information here.
Sunday
New Lebanon Flea Market in the Berkshires
435 Columbia Pike, New Lebanon, N.Y.
8 a.m. to 4 p.m.
Find treasures at this weekly flea market if weather permits.
More information here.
Local Love Arts Festival
The Common, Pittsfield
10 a.m.-3 p.m.
The inaugural Local Love Arts Festival will feature local artists showcasing their work, connecting with new audiences, and reminding our community that some of the region's most talented creators are right here in our own backyard. Visitors will enjoy artisanal vendor booths, the Berkshires Jazz Summer Showcase, food and beverages, a children's activity area with free face painting and balloon twisting, sidewalk chalk art with Pittsfield Parks and Recreation, and interactive arts experiences throughout the day. Hot Plate Brewing Co. will host an exclusive beer and wine garden with a view of the Main Stage.
More information here.
Adams Quaker Meeting House Hours
Maple Street Cemetery, Adams
1-4 p.m.
Free tours of the 1782 meeting house, place of worship of the family of Susan B. Anthony, born in Adams in 1820, through Oct. 11.
More information here.
Farmers Markets
Great Barrington Farmers Market
18 Church St.
Saturdays 9 a.m.- 1 p.m.
The market is open every Saturday through Nov. 14. Every week, locally grown food, flowers, and plants will be available, along with other local vendors. The market accepts and offers double SNAP, HIP, WIC, and Senior market coupons.
More information here.
Lee Farmers Market
The Town Park
Saturdays 10 a.m.-2 p.m.
The market offers locally grown produce, prepared foods, locally created arts and crafts, and herbal products through Oct. 10. 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 Farmers Market
Village Green
Sundays 10 a.m- 1 p.m.
The market has local vendors that offer a variety of goods, including produce, eggs, baked goods, jams, hand-knit items, maple syrup, and more through October.
More information here.
North Adams Farmers Market
Main Street
Saturdays 9 a.m.-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 through Oct. 31. Explore downtown North Adams and discover local businesses and fresh produce from local farms.
More information here.
Otis Farmers Market
2000 East Otis Road, Otis
Saturdays 9 a.m.-1 p.m.
Eggs, baked goods and desserts, microgreens, maple products, honey, pasture-raised pork, grass-fed beef, bison, elk, canned goods, jams, jellies & fruit butters and more through Oct. 10.
More information here.
Pittsfield Farmers Market
Pittsfield Common
Saturdays 9 a.m.-1 p.m.
Roots Rising, the region's first teen-run market, features live music, chef demos, workshops and children's activities through Oct. 10.
More information here.
West Stockbridge Farmers Market
Foundry Green
Thursdays 3-6 p.m.
Wide range of local producers and fare including vegetables, breads, teas, herbs, dairy, sweets, jams and crafts. Runs through Oct. 1.
More information here.
Williamstown Farmers Market
Spring Street
Saturdays 9 a.m.-1 p.m.
The market focuses on a wide range of local food and artisan vendors, as well as local services and music through Nov. 7.
More information here.
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