June 5 First Fridays Artswalk

Downtown Pittsfield Pittsfield

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

First Fridays at Five: The Housie Shakers

Persip Park 175 North Street, Pittsfield

Persip Park, 175 North Street, will feature a live performance by The Housie Shakers from 5 to 8 pm. Enjoy a beer garden from Hot Plate Brewing Co. and local food vendors within the vicinity. The Housie Shakers bring a variety of styles to the mix, with wide-ranging covers and original music spanning rock, blues,…

First Fridays at Five: Busker Robin O’Herin

Palace Park 116 North Street, Pittsfield

Busker Robin O'Herin will be popped up in Palace Park (near 122 North Street) from 5 to 8 pm. A three-time Boston Blues Finalist, and 2023 Albany Blues Challenge Finalist, Robin O'Herin, specializes in historically rich, often interactive concerts that include original and traditional American music, for small listening rooms, libraries, festivals, schools and more.…

First Fridays at Five: artistic face painting with Melissa Matsuki Lillie

Palace Park 116 North Street, Pittsfield

Palace Park will feature free artistic face painting with Melissa Matsuki Lillie. Melissa Matsuki Lillie is painter whose artwork references natural forms using a personal visual language of vibrant colors and complex layers to reflect on the macroscopic and microscopic world. Her paintings evoke a sense of space that has been flattened and layered, revealing…

Family Fun Zone at First Fridays at Five

Downtown Pittsfield Pittsfield

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 914 LOCK INC, ALZ.0rg, Barrington Stage Company, BART Charter Public School, Berkshire Art Center, Berkshire Athenaeum, Berkshire Coalition for Suicide Prevention, Berkshire County Football Officials Association,…

June First Fridays at Five

Downtown Pittsfield Pittsfield

The City of Pittsfield, Downtown Pittsfield, Inc. (DPI), and the Downtown Pittsfield Cultural Association (DPCA) have announced details for the second First Fridays at Five of the 2026 season. The event on Friday, June 5 presented by MountainOne, will feature live music and dance, art, family fun, shopping, food, and entertainment throughout downtown Pittsfield. Attendees…

First Fridays at Five: Bowey the Clown

Downtown Pittsfield Pittsfield

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

Dance and Drum with the Berkshire Rhythm Keepers

Downtown Pittsfield Pittsfield

On North Street at the South end of the road closure will be “Dance and Drum with the Berkshire Rhythm Keepers.” There will be a free Berkshire Rhythm Keepers performance from 5:45 to 6:30 pm, followed by a free dance class with Noel Staples-Freeman featuring live drumming by Aimée Gelinas, Dan Cohen, and the Berkshire Rhythm…