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 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

- The Housie Shakers
- 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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North Street at the South end of the road closure (near Park Square), 5 to 8 pm

- “Dance and Drum with the Berkshire Rhythm Keepers”

5:45 to 6:30 pm: Berkshire Rhythm Keepers performance
6:45 to 7:30 pm: Free dance class with Noel Staples-Freeman featuring live drumming by Aimée Gelinas, Dan Cohen, and the Berkshire Rhythm Keepers advanced drummers

Rain location: WANDER, 34 Depot Street

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28 North Street, 5 to 8 pm

- The "Resurrection Off-road Team" will host a “Touch an ATV” event in front of the Allegrone Building at 28 North Street.

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Dunham Mall, 100 North Street, 5 to 8 pm

- Community Paint Party!

Stop by Dunham Mall, pick up a brush, and help paint a mural that celebrates the best of Pittsfield. All ages and abilities are welcome. No experience is necessary!

Rain location: AdLib, 215 North Street

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Palace Park, 122 North Street, 5 to 8 pm

- Busker Robin O'Herin, singer-songwriter
- Free artistic face painting with Melissa Matsuki Lillie
- 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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North Street

Makers Market:

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 items, and packaged foods and sweets. Makers include ATK Customs, Auntie Kat's Gift Shop, Baked! Pastries & More, BareBone Roots, Berkshire Henna, BerkshireSci Biscuits LLC, Black Bear 3D, Braidy Bunch, Cookie's Cupcakes, Dragonfly Dreams, Glimmerhold Artistry & Tiffs Trinkets, Hilltown Hemlock Studio, LAMARÍA, Leann's Lovies, Leo's Bargain Boutique , little country gifts, ManiSetGo, Mountain Roots Artistry, Paparazzi Accessories, Pearls & Pillows, Sisterhood of the Traveling Crafts, and Truffles by Tarah.

Food Vendors:

Check out a variety of food vendors including Alchemy Events Mobile Bar, 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, La Chalupa & La Enchilada, and Williams Street Market and Deli.

Family Fun Zone:

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, 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, Berkshire Museum, Berkshire Woodworkers Guild, BRPC/ SPARK - BE3C Coalitions, Department of Children and Families, Elizabeth Freeman Center, Foster MA/Adopt MA, Girl Scout Troop 64834, Jacob's Pillow Dance Festival, Mental Health Support For Families, NBT Bank, The Mount/Edith Wharton Cultural Center, and VFW Post 448.

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, Roots and Dreams and Mustard Seeds, 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.

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, 2026. 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.