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, 5 to 7 pm
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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
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, 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, 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.
See a full event listing below!
Persip Park, 175 North Street, will feature a live performance by Nate Martel and his band from 5 to 8 pm. Enjoy a beer garden from Hot Plate Brewing Co. and local food vendors within the vicinity.
Powerhouse vocalist, songwriter, and guitarist, Nate Martel, currently resides in Easthampton, MA, but he was born and raised in Northern Berkshire County. His music is soulful, unique, and infectious, ranging from roots rock to funky soul to heartfelt ballads. Nate has been playing live shows since high school, and now twenty years later, he is honored to have shared the stage with a mighty and eclectic array of mainstream, national acts, including The Revivalists, Black Joe Lewis, Ryan Montbleau, Bernie Worrell, and even Ghost Face Killer/members of Wu Tang. Regionally, he has performed at some of the finest music venues the Northeast has to offer, including The Paradise in Boston, The Brooklyn Bowl, both of The Stone Church venues in Brattleboro, VT and Newmarket, NH, The Adams Theater in his hometown, and countless times at The Iron Horse in Northampton, MA.
Nate is joined by a stellar cast of musicians: Darby Wolf from the Reckoners, Matt Schofield on organ and keyboards, Zach Gregory from Lush Honey on bass, and Marcel Leclaire on drums.
In the case of inclement weather, Nate Martel will be at Price Memorial A.M.E. Zion Church, 27 East Street.
Weather permitting, artist Jan Rapisarda will be at work on a new, large-scale mural at 7 North Street, and the public is invited to watch him create live during the First Fridays at Five. The new mural is a celebration of the people, recreation, nature, and wildlife that make our region special. There will also be art making activities for families to engage with, and a busker drummer, Brian Colbert will be playing live.
School Street will feature a Beer Garden with Hot Plate Brewing Co., lawn games, and busker, Micheal Aaron from 5 to 8 pm.
Michael Aaron is not just another singer-songwriter; he’s a musical craftsman whose eclectic blend of folk and indie rock reflects a lifetime of diverse experiences and influences. Drawing inspiration from a diverse array of artists, Michael infuses his music with raw emotion and introspective lyricism, capturing the essence of life’s joys and struggles. His sound is a tapestry woven with the threads of his influences, from the melodic sensibilities of The Beatles to the earnest storytelling of Wilco and the infectious energy of Guster.
In the case of inclement weather, music with Micheal Aaron will be inside Hot Plate Brewing Co. at 1 School Street from 5 to 7 pm.
There will be a Kids’ Bike Rodeo in the Palace Park Parking Lot from 5 to 8 pm presented by the Berkshire Bike Path Council, AAA, and Massachusetts Safe Routes to School in honor of Bike Month. This event is open to young riders, elementary and middle school children, and their families and will feature 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.
Ronnie’s Harley-Davidson is celebrating 70 years in business this year and will be joining First Fridays at Five near the South end of the road closure for a touch an ATV and UTV event.
Busker Autumn Phoenix will be popped up in Palace Park (near 122 North Street) from 5 to 8 pm. Autumn an award-winning singer-songwriter who will be performing original material and some covers. She is also a professional photographer!
Downtown Pittsfield, Inc. and First Fridays Artswalk will feature Peter Vacchina as the May “Art in the Park” artist.
Peter will be popped up in Palace Park (near 122 North Street) from 5 to 8 pm, inviting the community to add pieces to a “made-on-the-spot” mosaic and discussing his process with all who are interested.
Peter is a sculptor working primarily in marble, mosaic, and the occasional ice sculpture. His art reflects his personal life experiences, particularly his time living and traveling abroad. Before becoming a full-time artist in Pittsfield, Peter lived and taught science in Belgium, Brazil, Mexico, England, Italy, and California. “I appreciate the challenge of working in marble and its potential to last for centuries. In my marble sculptures, I seek to invoke memory in the way a scent or sound might, and in doing so inspire heartfelt stories in the viewer.”
“Art in the Park” is supported in part by the Feigenbaum Foundation.
“Art in the Park” is supported in part by a grant from the Mass Cultural Council, and a grant from the Pittsfield Cultural Council, a local agency which is supported by the Mass Cultural Council, a state agency.
In the case of inclement weather, “Art in the Park” with Peter Vacchina and music with Autumn Phoenix will be inside the Lichtenstein Center for the Arts at 28 Renee Avenue.
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 Auntie Kat’s Gift Shop, Bake My Day, Baked! Pastries & More, BareBone Roots, Berkshire Henna, Braidy Bunch, Creative Creations, 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.
Check out a variety of food vendors including 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.
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 ALZ.0rg, BART Charter Public School, Berkshire Art Center, Berkshire Athenaeum, Berkshire Coalition for Suicide Prevention, 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, and VFW Post 448.
Bowey the Clown will be crafting free balloon creations in front of Crawford Square at 137 North Street.
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, 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. A portion of North Street will be closed during the event.
The City of Pittsfield’s DPW will present their Integrated Water Resources Management Plan which will evaluate the City’s drinking water, wastewater, and stormwater systems. It aims to balance sustainable growth, environmental protection, and affordability while identifying infrastructure needs and management strategies.
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.
North Street will be closed from Park Square to Columbus Avenue on Friday, May 1 from 3 to 8:30 pm. Drivers are asked to seek alternate routes during this timeframe and follow appropriate detours. In addition, a parking restriction will be in place on North Street between Park Square and Columbus Avenue starting at 2 pm on Friday.