‘First Fridays at Five’ in Pittsfield to celebrate United Way’s 100th anniversary

PITTSFIELD, Mass. (WWLP) – The City of Pittsfield, Downtown Pittsfield, Inc. (DPI), and the Downtown Pittsfield Cultural Association (DPCA) are gearing up for a vibrant August edition of “First Fridays at Five,” scheduled for August 2.

The monthly event, designed to enliven downtown Pittsfield, will feature a rich blend of live music, art, dance, family-friendly activities, shopping, food, and entertainment.

This month’s celebration coincides with the Berkshire United Way’s (BUW) 100th Birthday Bash, supported by The Guardian Life Insurance Company of America as the presenting sponsor. DJ Pup Daddy, also known as Tim Dupree of Pup Daddy Productions, will headline the event, spinning dance classics from the ’60s to today on the mobile City Stage. The Berkshire United Way team, alongside partner organizations, will provide crafts, games, and giveaways, including a Book House offering free children’s books. Attendees are encouraged to support BUW’s annual August School Supply Drive by donating items to “Fill a Ford,” generously provided by Johnson Dealership Inc.

In addition to celebrating BUW’s centennial, the event will include interactive dance performances by the Wandering Dance Society at Persip Park, featuring a lesson in East Coast Swing by Rushelle Bowie and a performance by Youth Alive, Inc. The latter, a multicultural, community-based organization, will showcase a blend of step, dance, and drumline.

Sottile Park will host the Bright Starr 360 Photo Booth, inviting guests to take photos to commemorate the BUW’s milestone. Pottery enthusiasts can visit Palace Park, where Jim Horsford will demonstrate pottery making, inviting attendees to participate.

The newly established Hot Plate Brewing Co. will set up a Beer Garden on School Street, complemented by food from Otto’s Kitchen & Comfort and live music from the local cover band Mr. Doubtfire. The Makers’ Market will line North Street, offering a variety of handmade products from local artisans, while the Family Fun Zone at Dunham Mall will provide activities like face painting, arts & crafts, and balloon creations.

The event also includes the First Fridays Artswalk, featuring dozens of artists at venues throughout downtown Pittsfield, including the Berkshire Art Center, which will offer free drop-in art-making from 5:30 to 7:30 p.m. A free art shuttle will transport visitors between the Clock Tower Artist Studios and City Hall, offering easy access to the diverse artistic displays.

Several downtown restaurants will serve food outdoors during the event, with additional live music at The Tap at Dottie’s Coffee Lounge/Dorothy’s Estaminet from 7 to 10 p.m. First Fridays at Five is a collaborative effort to highlight the cultural vibrancy of Pittsfield, with North Street closed from Park Square to Depot Street from 3 to 8 p.m. and a parking restriction in place starting at 2 p.m.

For a complete list of events and further information, visit their website.

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