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Weekend Outlook: Festivals, Fundraisers, and More
By Sabrina Damms, iBerkshires Staff
12:37PM / Thursday, September 18, 2025
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There are lots of events in and around Berkshire County this weekend including festivals, fundraisers, and more. 
 
Editor's Pick
 
Lee Founders Weekend 
Friday, Sept. 19 through Sunday, Sept. 21
 
Nearly 250 years ago, the town of Lee was founded and this weekend community members will celebrate the rich history and vibrant spirit of its founders. 
 
The three-day festival features a variety of activities including parades, live music, food vendors, fireworks, and more. 
 
It kicks off Friday with a Lee Historical Society Cemetery Talk at Fairmont Cemetery at 10 a.m. followed by the beloved Taste of Lee event. From 5 to 9 p.m. Main Street is closed to make room for live music, hay wagon rides, race car displays, Irish dancers, and food from local restaurants and eateries. 
 
The fun continues on Saturday with several activities including the founders hometown parade, an Antique Fire Truck Show, the Lee Lions Founders Weekend Car Show, live music, food, and more. 
 
Finally, on Sunday, the festivities conclude with yoga, raffles, cornhole tournament, food, vendors, live music, and its new dog parade. 
 
Full festival line-up here
 
Multiple Days
 
Freshgrass Festival 2022
Mass MoCA, North Adams
Time: Friday-Sunday
 
The Massachusetts Museum of Contemporary Art is hosting its annual Fresh Grass Festival. Thousands are expected to be in the city during the three-day event.
 
There will be live music throughout the grounds and at Joe's Field including performances by Greensky Bluegrass, Old Crow Medicine Show, Alison Brown, and many more. 
 
There will also be plenty of vendors on site selling merchandise, food, and drinks. A three-day adult pass is $213; see more on ticket prices and performance lineup here
 
RiverFest
Main Street, Cummington
Friday, Sept. 19, and Saturday, Sept. 20
 
The Cummington Cultural District is inviting people to celebrate the wild and scenic Westfield River that runs through the heart of the town. 
 
The event features hands-on activities led by artists, scientists, and humanists, focusing on themes related to the river, climate change, and ecosystems. Festivities include workshops, walks, guided movement, performances, and public artworks.
 
More information here.
 
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
 
Friday 
 
Circle of Stone Album Release Party
The Stationery Factory, Dalton 
Time: 8 p.m. 
 
Rock band Circle of Stone will be celebrating its release of its new album after taking a hiatus in the mid-2000s. 
 
The band released a limited extended play in 1995, gaining radio attention and becoming prominent in the late '90s and early 2000s, filling venues with a mixture of their original material and assortment of rock and hard rock covers.
 
Tickets range from $20 to 25. More information here.
 
A Taste of Ireland
The Colonial Theatre, Pittsfield 
Time: 7:30 p.m. 
 
After a successful Off-Broadway debut and international tour the "A Taste of Ireland—The Irish Music & Dance Sensation" is returning to the Berkshires. 
 
The performance features world-class performers from "Riverdance" and "Lord of the Dance," showcasing a blend of traditional Irish culture with modern elements.
 
Tickets are $49 and up. More information here
 
Musical Bingo 
Bluebird & Co., Hancock 
Time: 8 p.m. 
 
DJ Pup Daddy will be spinning tunes for this musical bingo event featuring 75 popular songs from a mix of boy bands like NSYNC, KNOTB and Backstreet Boys and hair bands such as Poison, Whitesnake and Def Leppard. 
 
There is no fee to play with three chances to win Bluebird gift cards for Single, Double, and Blackout SPINDLEs. 
 
More information here
 
Musical Bingo Fundraiser
The GOAT Sports Bar & Grill, North Adams 
Time: 6:30 p.m. 
 
There will be a game of musical bingo to raise funds to support A Walk to End Alzheimer's. Tickets are $25 per person, including 2 bingo cards; extra cards for $5 each. Tickets available now at Adams Community Bank Branches. 
 
More information here
 
Lee Founders Day Fireworks 
Visible from Main Street
Time: Around 8 p.m. 
 
During the Taste of Lee event, the town will kick off its Founders Weekend with a display of fireworks by Santore's World Famous Fireworks.
 
More information here
 
Saturday 
 
Retro Floyd: Experience Pink Floyd
The Stationery Factory, Dalton 
Time: 8 p.m. 
 
Pink Floyd tribute band Retro Floyd will be performing tunes by the rock band. They have been described as "Vocal Floyd" because they are the only band where every  member sings at least one lead vocal, or many lead vocals. 
 
Tickets range from $25 to $30. More information here.
 
Pickle Festival 
The Apple Barn, Bennington Vt. 
Time: 10 a.m. to 5 p.m. 
 
Celebrate all things pickle and the harvest season at The Apple Barn's Pickle Festival, featuring pickle-themed snack, live music, the "Big Dill" pickle competition, a 4H Fun Zone, a mini cider donut eating contest, a free photo booth, and more. 
 
There will also be a special appearance by its pickle mascot, Sir Pickleton.  
 
Smash the Stigma 
Great Barrington Town Hall
Time: noon to 3 p.m. 
 
South County Recovery Center will have a community based, family-friendly event, to raise awareness of people affected by substance use in South Berkshire County. 
 
The event will highlight available resources and create connections to reduce stigma associated with substance use disorder and recovery.
  
More information here
 
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 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
 
Rock the Pantry
The Colonial Theatre, Pittsfield
Time: 7 p.m. 
 
Pittsfield's South Community Food Pantry is having its first-ever benefit concert, celebrating the musical talent of the Berkshires while raising support for those in need. 
 
The stage will come alive with performances by local performances including The Wanda Houston Band, Billy Keane, Jackson DuCharme, and more. 
 
Tickets are $40 and up. More information here
 
Stand-up Comedy 
The Adams Theater
Time: 7:30 p.m. 
 
Comedians Richie Byrne, Mark Riccadonna, and Ashley Gutermuth will be performing. 
 
Byrne blends high-energy, family-friendly humor with observations. Riccadonna is a storyteller with a charismatic style that has taken him international. Gutermuth is a comedian and actor with sharp, relatable humor often drawn from her life as a military spouse. 
 
Tickets are $20 for general seating and $35 for priority seating. More information here
 
Springside Park Fall Cleanup 
Springside Park, Pittsfield 
Time: 9 a.m. to 1 p.m. 
 
Friends of Springside Park is having its annual fall clean-up. Volunteers can go to the check-in table at the North Playground, off 874 North Street. Bring your own gloves if possible, but bags, water, and instructions provided.
More information here
 
 
Greylock Photography Group Meet-Up: Greylock After Dark 
Mount Greylock Visitor Center, Lanesborough
Time: 1 to 2:30 p.m. 
 
Timothy Little, of Cape Nights Photography, will be offering one of his night photography workshops and will give a presentation of his Mount Greylock photography artworks for its Mount Greylock photography program. 
 
More information here
 
12th Annual Stone Skipping Festival 
Lake Paran, North Bennington, Vt. 
Time: noon to 5 p.m.
 
New England's only stone-skipping competition is open to pros and amateurs, young and old. Free admission to watch and a small fee to compete to try and break the world record of 88 skips and win some fudge. There will be rocks to buy for skipping, stone painting, and food for purchase.
 
More information here
 
Sunday 
 
Mountain Mindfulness
Mount Greylock Visitor Center
Time: 11 a.m. 
 
There will be yoga and a mindful nature walk led by Vicki Zacharewicz, who will encourage visitors to be mindful in an effort to reduce stress and gain inspiration from earth.
 
Visitors will be guided on a slow intentional journey to de-stress while connecting with nature through forest bathing, breath work, and meditation, culminating in a group sharing session.
 
More information here
 
Berkshire Opera Festival
Berkshire Community College, Pittsfield 
Time: 2 p.m. 
 
There will be a free screening of the Berkshire Opera Festival's 10th anniversary concert at the college's K111 Theater. 
 
The concert features some of opera's greatest hits performed by world-class artists from Berkshire Opera
Festival's previous seasons, accompanied by its orchestra and chorus.
More information here
 
 
One Man Play: Mr. Dickens Is Coming
Ventfort Hall Gilded Age Mansion & Museum, Lenox
Time: 7 p.m. 
 
British actor Gerald Charles Dickens, the great-great-grandson of the literary legend Charles Dickens, will be presenting his one-man theatrical performance of his ancestor's classic works in Mr. Dickens Is Coming. 
 
Tickets are $50 per person. More information here
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