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Nate Martel Band at Persip Park

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Persip Park 175 North Street, Pittsfield

Live performance by Nate Martel and his band from 5 to 8 pm in Persip Park, 175 North Street. Enjoy a beer garden from Hot Plate Brewing Co. and local […]

School Street Beer Garden & Busker, Michael Aaron

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North Street at School Street 1 School Street, Pittsfield

School Street will feature a Beer Garden with Hot Plate Brewing Co., lawn games, and busker, Micheal Aaron from 5 to 8 pm. Michael Aaron is not just another singer-songwriter; […]

Busker Autumn Phoenix

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Palace Park 116 North Street, Pittsfield

Busker Autumn Phoenix will be popped up in Palace Park (near 122 North Street) from 5 to 8 pm. Autumn an award-winning singer-songwriter who will be performing original material and […]

Bowey the Clown

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North Street

Bowey the Clown will be crafting free balloon creations in front of Crawford Sqaure at 137 North Street.

“Art in the Park” with Peter Vacchina

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Palace Park 116 North Street, Pittsfield

DPI. and First Fridays Artswalk will feature Peter Vacchina as the May “Art in the Park” artist. Peter will be popped up in Palace Park (near 122 North Street) from […]

Makers Market

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North Street

The Makers Market at First Fridays at Five will feature over a dozen local vendors selling handmade products such as crafts, clothing and accessories, candles, art, custom gift items, self-care […]

Bike Rodeo at Palace Park

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Palace Park 116 North Street, Pittsfield

There will be a Kids’ Bike Rodeo in the Palace Park Parking Lot from 5 to 8 pm presented by the Berkshire Bike Path Council, AAA, and Massachusetts Safe Routes […]

Live Mural Creation with Jan

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7 North Street

On Friday, May 1, weather permitting, artist Jan Rapisarda will be at work on a new, large-scale mural at 7 North Street, and the public is invited to watch him […]

May 1 First Fridays Artswalk

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Around Downtown

The First Fridays Artswalk in downtown Pittsfield begins its 5-month season (May through September) on Friday, May 1 from 5 to 8 pm as part of the City of Pittsfield’s […]

Family Fun Zone

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North Street

The Family Fun Zone at First Fridays at Five will feature free, interactive activities from local non-profit organizations including arts & crafts, games, and more. Participating organizations include ALZ.0rg, BART […]

May Opening with the Clock Tower Artists

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Clock Tower Artists 75 South Church Street, 3 Floor, Pittsfield

NEW FOR 2026: The Clock Tower Artists are excited to introduce rotating 2–3 person pop-up exhibits in our West Studios Lobby—alongside our regularly scheduled open studios—bringing even more variety and […]

Free

The Prom Musical

Featured The Prom Musical
Berkshire Community College 1350 West Street, Pittsfield

The Prom, Broadway’s new musical comedy—with issues—follows four Broadway stars on a hilarious mission to change the world and get a little publicity for themselves. So when they hear that […]

PHS Proteus presents Urinetown

Featured PHS Proteus presents Urinetown
Pittsfield High School 300 East Street, Pittsfield

Urinetown is a satirical Broadway musical set in a dystopian future plagued by a 20-year drought, where a corporate-government alliance bans private toilets. Citizens must pay to use public amenities, leading to […]

I’m Going to Graceland

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The Colonial Theatre 111 South Street, Pittsfield

Rev Tor & Friends return to The Colonial Theatre with an encore live performance of Paul Simon’s Graceland in celebration of the album’s 40th anniversary.

$30

I’m Going To Graceland

Featured
The Colonial Theatre 111 South Street, Pittsfield

Rev Tor & Friends Celebrate the 40th Anniversary of  Paul Simon’s Graceland with special guest Simon & Girlfunkel with an appearance by The BTG Youth Chorus Rev Tor & Friends […]

PHS Proteus presents Urinetown

Featured PHS Proteus presents Urinetown
Pittsfield High School 300 East Street, Pittsfield

Urinetown is a satirical Broadway musical set in a dystopian future plagued by a 20-year drought, where a corporate-government alliance bans private toilets. Citizens must pay to use public amenities, leading to […]

The Prom Musical

Featured The Prom Musical
Berkshire Community College 1350 West Street, Pittsfield

The Prom, Broadway’s new musical comedy—with issues—follows four Broadway stars on a hilarious mission to change the world and get a little publicity for themselves. So when they hear that […]

The Prom Musical

Featured The Prom Musical
Berkshire Community College 1350 West Street, Pittsfield

The Prom, Broadway’s new musical comedy—with issues—follows four Broadway stars on a hilarious mission to change the world and get a little publicity for themselves. So when they hear that […]

The Prom Musical

Featured The Prom Musical
Berkshire Community College 1350 West Street, Pittsfield

The Prom, Broadway’s new musical comedy—with issues—follows four Broadway stars on a hilarious mission to change the world and get a little publicity for themselves. So when they hear that […]

PHS Proteus presents Urinetown

Featured PHS Proteus presents Urinetown
Pittsfield High School 300 East Street, Pittsfield

Urinetown is a satirical Broadway musical set in a dystopian future plagued by a 20-year drought, where a corporate-government alliance bans private toilets. Citizens must pay to use public amenities, leading to […]

PHS Proteus presents Urinetown

Featured PHS Proteus presents Urinetown
Pittsfield High School 300 East Street, Pittsfield

Urinetown is a satirical Broadway musical set in a dystopian future plagued by a 20-year drought, where a corporate-government alliance bans private toilets. Citizens must pay to use public amenities, leading to […]

The Prom Musical

Featured The Prom Musical
Berkshire Community College 1350 West Street, Pittsfield

The Prom, Broadway’s new musical comedy—with issues—follows four Broadway stars on a hilarious mission to change the world and get a little publicity for themselves. So when they hear that […]

The Prom Musical

Featured The Prom Musical
Berkshire Community College 1350 West Street, Pittsfield

The Prom, Broadway’s new musical comedy—with issues—follows four Broadway stars on a hilarious mission to change the world and get a little publicity for themselves. So when they hear that […]