The 19th Pleasantville Music Festival took place on Saturday, July 12 at Parkway Field in Pleasantville, NY. The day featured fifteen acts across three stages, culminating with Southern California’s Dawes closing out the evening.

Dawes, Pleasantville Music Festival 2025 — Dawes

The festival prides itself on showcasing local bands as part of its performance roster. Each year, young musicians from surrounding counties vie for opening slots by participating in a Battle of the Bands competition. The winners are then invited to perform at the festival.

Cabin Fever from Chestnut Ridge, NY garnered top honors in the battle and earned the opportunity to open the main stage. The band backed up their win with a stellar set. Second-place winners UR SO received the nod to kick off the Pamnation Party Stage.

With eighteen years under its belt, the festival understands that the future of music lies with its youngest fans. The Party Line Chill Tent Stage ensured that even the littlest music lovers were represented. Opening the stage, The Rock and Roll Playhouse performed a tribute to Taylor Swift. Children, along with their parents, were encouraged to dance and sing along to their favorite songs. Even with some of the children just learning to walk, these young rockers didn’t sit idly—they boogied joyfully in front of the stage.

The day began with an overcast sky, but as the clouds dissipated and temperatures rose, so too did the caliber of the music. Each stage had its own flavor. The Pamnation Party Stage featured alt-indie bands, and the open field in front of it gave fans an unobstructed view and space to absorb the energy from bands like Jelly Kelly, Big Girl, and Boston’s Bermuda Search Party.

The Party Line Chill Tent Stage offered soul, blues, and more. Jennifer Hartswick, an original member of the Trey Anastasio Band, was joined by guitarist Nick Cassarino in a powerful duo. New York Blues Hall of Fame Master Blues artist Chris Bergson brought his band to the tent, supported by Ellis Hooks and Alexis P. Suter. North Carolina’s Nikki Hill took the roof off the tent with her soulful, sensual, and bold vocal tones, backed by a killer band.

The main stage presented national headlining acts, including Brown Eyed Women which is an all-woman ensemble celebrating the music of the Grateful Dead. Four-time Grammy nominee Robert Randolph brought his pedal steel guitar and rock ’n’ roll swagger to Pleasantville, joined during his set by Westchester’s own Jessica Lynn.

As the sun set, brothers Taylor and Griffin Goldsmith—aka Dawes—closed out the festival. Opening with “Things Happen,” the band delivered a set spanning their nine studio albums, including “Roll With the Punches,” “A Little Bit of Everything,” and ending the night with a heartfelt performance of “All Your Favorite Bands.”