Downtown Pittsfield’s First Fridays at Five Is Back

After a long winter, downtown Pittsfield is about to come alive again.

The City of Pittsfield, Downtown Pittsfield, Inc., and the Downtown Pittsfield Cultural Association have announced details for the first First Fridays at Five of the 2026 season, set for Friday, May 1. The event is presented by AccessPlus and runs from 5 to 8pm along North Street, which will be closed from Park Square to Columbus Avenue starting at 3pm. Drivers should plan alternate routes.
Bring a chair. There is a lot to sit and enjoy.

The Music

The main stage at Persip Park, 175 North Street, will feature Nate Martel and his band from 5 to 8pm. Martel is a Northern Berkshire native now based in Easthampton, and his sound is hard to pin down in the best possible way. Think roots rock, funky soul, and heartfelt ballads all rolled into one. Over the past two decades he has shared the stage with The Revivalists, Black Joe Lewis, Ryan Montbleau, and even members of Wu-Tang Clan. He has performed at The Paradise in Boston, Brooklyn Bowl, and countless times at The Iron Horse in Northampton. He is joined by Darby Wolf of the Reckoners, Matt Schofield on organ and keyboards, Zach Gregory of Lush Honey on bass, and Marcel Leclaire on drums. Hot Plate Brewing Co. will have a beer garden at Persip Park as well.

Over on School Street, singer-songwriter Michael Aaron performs from 5 to 8pm alongside another Hot Plate beer garden and lawn games. Aaron draws from folk and indie rock, with influences ranging from The Beatles to Wilco to Guster. Busker Autumn Phoenix will also be performing original material and covers in Palace Park near 122 North Street.
If the weather turns, Nate Martel moves indoors to Price Memorial A.M.E. Zion Church at 27 East Street.

The Art

Weather permitting, artist Jan Rapisarda will be live at work on a brand new large-scale mural at 7 North Street. The mural celebrates the people, recreation, nature, and wildlife of the Berkshires, and the public is invited to watch it take shape in real time.
Palace Park will also feature sculptor Peter Vacchina as the May "Art in the Park" artist. Peter works primarily in marble, mosaic, and the occasional ice sculpture. He will be inviting the community to contribute to a made-on-the-spot mosaic and talking through his process with anyone who stops by. Before becoming a full-time artist in Pittsfield, Peter lived and taught science in Belgium, Brazil, Mexico, England, Italy, and California. That is quite a resume.

Also in Palace Park, Jim Horsford will be hosting a free live pottery demonstration from 5 to 8pm, inviting people to help him make pots on the wheel. Jim spent 30 years teaching art at Herberg Middle School and has been teaching pottery at the Lichtenstein Center for the Arts since 2000. His finished pieces will be available for purchase.
If the weather does not cooperate, the art and music in Palace Park moves inside to the Lichtenstein Center for the Arts at 28 Renee Avenue.

The Family Stuff

The Kids' Bike Rodeo runs from 5 to 8pm in the Palace Park Parking Lot, presented by the Berkshire Bike Path Council, AAA, and Massachusetts Safe Routes to School in honor of Bike Month. Young riders from elementary through middle school can get a bike tune-up, learn safety tips, and practice their skills. Note that bikes are not allowed within the First Fridays footprint, so plan to walk your bike through or enter via Renee Avenue off Fenn Street.

Ronnie's Harley-Davidson, celebrating 70 years in business this year, will be near the south end of the road closure with a touch-an-ATV and UTV event. Bowey the Clown will be making free balloon creations in front of Crawford Square at 137 North Street.
The Family Fun Zone features free interactive activities from more than a dozen local nonprofits including the Berkshire Athenaeum, Elizabeth Freeman Center, Girl Scout Troop 64834, and the Berkshire Coalition for Suicide Prevention, among others.

The Food and Shopping

The Makers Market brings over a dozen local vendors selling handmade goods including crafts, candles, jewelry, clothing, and baked goods. The food truck lineup includes BB's Hot Spot, Cocineras Latinas LLC Coop, D's Island Food Truck, Full Belly FEWD TRUCK, Grampie's Dog House, Just Kickin It Bar B Que, La Chalupa, and Best Damn Espresso, among others.

First Fridays at Five returns June 5, August 7, and September 4. For the full schedule and event details, visit lovepittsfield.com/first-fridays.