The City of Pittsfield, Downtown Pittsfield, Inc. (DPI), and the Downtown Pittsfield Cultural Association (DPCA) have announced details for the first First Fridays at Five of the 2026 season. The event on Friday, May 1 presented by AccessPlus, will feature live music, art, family fun, shopping, food, two beer gardens, and entertainment throughout downtown Pittsfield. Attendees are encouraged to bring their own chairs so they can sit and enjoy a variety of food, beverages, and entertainment.

Persip Park, 175 North Street, 5 to 8 pm
- Nate Martel and his band
- Beer garden with Hot Plate Brewing Co.
- Local food vendors
Rain location: Price Memorial A.M.E. Zion Church, 27 East Street
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7 North Street, 5 to 8 pm
- Weather permitting, artist Jan Rapisarda will be at work on a new, large-scale mural
- Art making activities for families
- Busker Brian Colbert, drummer
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School Street, 5 to 8 pm
- Beer Garden with Hot Plate Brewing Co.
- Lawn games
- Busker Micheal Aaron, singer-songwriter
Rain location: Hot Plate Brewing Co., 1 School Street
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Palace Park Parking Lot, 5 to 8 pm
Kids’ Bike Rodeo open to young riders (elementary and middle school aged) and their families
-Bike check-ups, bike safety, and a place to practice riding skills.
As bikes are not allowed within the First Fridays at Five footprint, we ask that you walk your bike through this area or ideally enter Palace Park via Renne Avenue off Fenn Street.
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Palace Park, 122 North Street, 5 to 8 pm
- Busker Autumn Phoenix, singer-songwriter
- “Art in the Park” with Peter Vacchina, interactive mosaic making
- Live Pottery Demo with Jim Horsford
Rain Location: Lichtenstein Center for the Arts, 28 Renee Avenue
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North Street in front of Crawford Square, 137 North Street
Bowey the Clown
-Crafting free balloon creations!
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South end of the road closure (near Park Square)
Ronnie’s Harley-Davidson celebrates 70 years in business
-Touch an ATV and UTV event
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North Street
Makers Market:
Makers include ATK Customs, Auntie Kat’s Gift Shop, Bake My Day, Baked! Pastries & More, BareBone Roots, Berkshire Henna, BlossomBun, Braidy Bunch, Creative Creations, EllieB, Glimmerhold Artistry & Tiffs Trinkets, Hid In Gems, Hilltown Hemlock Studio, Lamaria, Leann’s Lovies, little country gifts, ManiSetGo, Pearls & Pillows, Plushy Pals, Sisterhood of the Traveling Crafts, Sunshine Jewelry, and Truffles by Tarah.

Family Fun Zone:
Participating organizations include ALZ.0rg, Barrington Stage Company, BART Charter Public School, Berkshire Art Center, Berkshire Athenaeum, Berkshire Coalition for Suicide Prevention, Berkshire County Head Start, Berkshire County Kids Place, Berkshire District Attorney's Office, Berkshire Environmental Action Team, Berkshire Medical Center's Behavioral Health Unit Council, Department Of Children and Families, Elizabeth Freeman Center, Girl Scout Troop 64834, Mental Health Support For Families, NBT Bank, “Stand Up, Berkshires” and VFW Post 448.

Food Vendors:
BB's Hot Spot, Berkshire Kettle Creations and Lemonade, Best Damn Espresso, Cocineras Latinas LLC Coop, D's Island Food Truck, Full Belly FEWD TRUCK, Grampie’s Dog House, Just Kickin It Bar B Que, and La Chalupa & La Enchilada

First Fridays Artswalk:
First Fridays Artswalk will showcase artists at venues throughout downtown Pittsfield from 5 to 8 pm including Clock Tower Artists, Framework by Downtown Pittsfield, Inc., Hotel on North, Indie Readery and Records, Lichtenstein Center for the Arts, Pittsfield’s City Hall, Sanctum Gallery, Solarium Plant Shop, and the Soda Chef. Follow a virtual walking tour on the free Downtown Pittsfield App and enjoy opening receptions with the artists.
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First Fridays at Five is led by the City of Pittsfield and Downtown Pittsfield, Inc. and will take place in downtown Pittsfield on May 1, June 5, August 7, and September 4. A portion of North Street will be closed during the event.

Season partners and sponsors include AccessPlus, MountainOne, Guardian, and Mill Town Foundation.

For more information and a full event listing, visit https://lovepittsfield.com/first-fridays.