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Weekend Outlook: Live Music, a Festival, and More
By Sabrina Damms, iBerkshires Staff
12:11PM / Friday, May 26, 2023
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Berkshire county and the surrounding areas are having a variety of events including live musical performances, comedy nights, and more. 
*Do you want your market or event included in the outlook? Email
Find Memorial Day events here.

Editor's Pick:

MayFest 2023
Downtown Bennington, Vt.
Time: 10 a.m. until 5 p.m. 
Main Street will be closed this Saturday for Bennington's MayFest to celebrate spring.
The event features music, food, performances and more. More than 95 vendors will line the street offering a range of products, from handmade jewelry, clothing, sculpture, and more. 
There will be many different types of live performances throughout the day on four separate stages. 
More information here


BAAMS Third Anniversary Concert
Adams Theater, Park Street
Time: 7:30 p.m.
The Berkshires Academy for Advanced Musical Studies celebrates three years with a night of live musical performances from the school's faculty, students, and special guests. This event will be the first performance in the newly-renovated Adams Theater's 2023 Spring/Summer WIP Series. See less
More information and tickets here
Live Music 
Big Elm Brewing, Sheffield
Time: 5 until 7 p.m.
There will be a performance by local musician Lauren Pellegrino. More information here
Salsa Night
The Stationery Factory, Dalton
Time: 7 p.m. 
The Wandering Dance Society is having a Salsa Night as part of its community dance initiative produced by Mill Town Foundation in association with Jacob's Pillow.
The night kicks off with lessons with Berkshire Salsa instructor Alan Franco followed by an open dance floor at 8 p.m.
Tickets are $10. If ticket price is a barrier to attend this event, contact
More information here


Remembrance Ride 2023
Dalton American Legion
Time: 10 a.m. 
The Legion is having its annual Memorial Day ceremony with a scenic ride to the Locker Room in Lee.
The ceremony is open to the public and you don't have to have a motorcycle to attend. 
Registration for the ride starts at 10  and the Memorial Day ceremony at 11.
More information here
The Brews Cruise
Hot Plate Brewing Co.
Time: 7:30 p.m.
Take a social ride in downtown Pittsfield this Memorial Day weekend. 
The casual 5-mile loop starts and ends at Hot Plate Brewing Co. Following the ride, their will be an hourlong social featuring a prize giveaway. 
More information here
Canna Provisions Live Music
Locker Room Sports Pub, Lee
Time: 7 p.m. 
There will be a live performance by local folk, alternative country, and acoustic rock musician Jack Waldheim. The show is presented by Canna Provisions. 
More information here


Berkshire Choral International in Concert
Tanglewood, Stockbridge
Time: 2 p.m. 
The nonprofit educational institution Berkshire Choral International will perform  works on the theme of home.
Tickets are just $15 general admission or $5 for anyone under 18. Tickets here
Live Musical Performance 
Starving Artist Cafe, Lee 
Time: 11 a.m. 
Singer and Songwriter Kenn Morr, of the Kenn Morr Band, will be having a solo performance featuring some of the band's songs. 
More information here
Domingo Brunch Ride
Dottie's Coffee Lounge, Pittsfield
Time: 10 a.m. 
Take a social ride in downtown Pittsfield and enjoy brunch at Dottie's with live music until noon. 
More information here
Comedy Night 
Stationary Factory, Dalton 
Time: 7:30 to 10:30 p.m.
Comedians Ted Alexandro, Andy Pitz and Shaun Eli will perform. The performances are presented by Liberty Comedy. 
More information here.
Preservation Month: A Tower of Remembrance
Mount Greylock State Reservation
Time: 1 and 2 on Sunday & Monday
Explore the story of Mount Greylock's historic Massachusetts Veterans War Memorial Tower, the commonwealth's tribute to the men and women who gave their lives in the service of their country.
The 93-foot tall monument on the state's highest summit is crowned with a beacon light that can be seen for miles. The 30-minute tour will highlight the recently completed $2 million restoration.
This program is free, all ages are welcome and the tour route is wheelchair accessible. Meet at the War Memorial. Children must be accompanied by an adult. A parking fee may apply.
More information: 413-499-4262

Multiple Days:

Drury Band Celebrates 100 Years 
The Drury Alumni Concert will be held this weekend coinciding with the band's centennial. 
This year, the concert will be a little different and will take place over two days.
On Friday, May 26, at 7 p.m.
The current Drury Jazz/Rock Band will play at the Elks on Friday at 7 and the Alumni Rock Band at 8.
The main event is Saturday, when the full alumni band will play a selection of six songs featuring different conductors including Carl Jenkins and Roger LaRocca. The concert will be held in the Drury High School auditorium.
More information here
Roxie's Barkery Retail Anniversary Celebration 
Roxie's Barkery, North Adams 
Bring your pups to Roxie's Barkery this Saturday and Sunday to celebrate its one-year anniversary in its Norad Mill location.
The weekend features free cakes for your pups, Bingo and raffles. Have your photo taken with your pup so the polaroid picture can be added to their poster.  
The festivities will take place on Saturday from 11 until 3 p.m. and Sunday from 11 until 2. Check out our last article on the business here.
More information on the event here

Farmer's Markets:

Pittsfield Farmers Market

The Common, Pittsfield
Time: 9 to 1. 
Powered by Roots Rising, the market is open every Saturday rain or shine. 
Each week the market will have fresh locally grown fruits and vegetables, along with meat, eggs, cheese, baked goods by local vendors. Participants can shop for flowers, and artisan goods while listening to music and participate in family activities. 
For more information, visit the website
Great Barrington Farmers Market
18 Church St., Great Barrington
Time: 9 to 1. 
The market is open every Saturday.  
Every week there will be locally grown food, flowers, and plants along with other local vendors. 
More information here
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