One of the most innovative and influential pedal steel guitarists of his generation, multi Grammy nominated, Emmy award winner Robert Randolph, blends gospel, rock, blues, and soul in a way that speaks to both his musical roots and modern-day artistry. With Preacher Kids, his solo debut scheduled to drop on June 27th, he charts a new career path that leads right through the Pleasantville Music Festival for a thrilling collaboration with Country Rock star Jessica Lynn.
Jessica Lynn brings her high-energy country-pop sound back to the Pleasantville Music Festival. Known for her dynamic performances and warm, approachable style, Jessica has toured in over 14 countries and topped the digital country charts in both the U.S. and abroad. She’s opened for legends like Keith Urban and Brad Paisley, starred in national TV specials, and just released her latest hit album, All I Own. With catchy songs, great musicianship, and a whole lot of heart, Jessica delivers an unforgettable concert experience.
Brown Eyed Women is an ensemble of powerful female players from popular bands around the country, celebrating the music of the Grateful Dead with a unique spin. Their high-caliber musicianship and shared love of the Dead drew them together. This band is decidedly different in a field brimming with tribute acts. BEW brings authentic jams and a soulful new approach to the familiar Grateful Dead catalog.
Sure to raise the roof off the Chill Tent, Chris Bergson Band is "gut-busting, horn-bedecked NY blues" (MOJO). They’re led by NY Blues Hall of Famer internationally acclaimed guitarist, singer/songwriter Chris Bergson whose latest album Comforts of Home garnered Four Stars in MOJO and was named one of Soul Bag magazine's Best Albums of 2024. Chris is joined by special guests Ellis Hooks whose soulful voice is reminiscent of the great soul men like Sam Cooke and Otis Redding (Blues Magazine), and Alexis P. Suter, who was a regular at Levon Helm’s legendary Midnight Rambles in Woodstock.
Bermuda Search Partydelivers an electrifying blend of indie-pop, funk-infused grooves, and soaring brass melodies, creating a sound that feels like pure celebration. Their music is built on infectious hooks, dynamic vocal harmonies, and smooth yet powerful trumpet and trombone lines. Whether on record or on stage, their songs pulse with energy, striking a balance between heartfelt lyricism and danceable, feel-good rhythms that lift spirits and get crowds moving.
Nikki Hill is a soul singing, bar rocking, roots revivalist hailing from North Carolina. Her music is a fertile mix of all of the gospel, R & B, soul, pop and hip hop of her childhood and teenage years and the Rock and Blues she picked up living over the years along the Mississippi River – in St. Louis, Missouri, New Orleans, Louisiana, and currently Memphis, Tennessee. Her band finds a muscular groove and delivers it with Nikki's signature vocal swagger and irrepressible stage presence. “If Tina Turner and Little Richard had a daughter and raised her with the help of uncles James Brown and Chuck Berry, she’d be like Nikki Hill.” — LA Weekly
Their big-hearted songs, filled with brute force guitarwork and earwormy wry, songwriting (an "I love making minimum wage!" chorus) make Big Girl a can't miss on the Party Stage.
It's indie pop at its most appealing: jarring, cathartic, punk energy, with knotty arrangements, wrapped in hook filled pop songs.
Jelly Kelly is a New York City-based indie rock band blending post-punk grit with dreamy synth textures and infectious hooks. What began as a side project for Monogold’s Keith Kelly has evolved into a genre-blurring sound that feels both familiar and unexpected. Joined by Jared Apuzzo (drums), Nicolas Dube (guitar), Marina Ross (bass), and Brendan Sullivan (keys), the band crafts moody, melodic tracks with cool confidence. The name, once a childhood taunt, now flies like a flag—defiant, memorable, and uniquely their own.
Trumpeter and vocalist Jennifer Hartswick and guitarist/vocalist Nick Cassarino share a rare musical chemistry that’s been honed over nearly two decades of collaboration. Both born and raised in Vermont, the duo brings a rich blend of soul, joy, and sophistication to their intimate acoustic performances. Hartswick, an original member of the Trey Anastasio Band, is celebrated for her powerful vocals, stunning trumpet work, and magnetic stage presence, having performed with legends like Herbie Hancock, Phish, and The Rolling Stones. Cassarino, known for his soulful guitar playing and velvety voice, has earned acclaim through his work with The Nth Power and Big Daddy Kane. Together, their performances are heartfelt, spontaneous, and deeply connected—offering audiences an unforgettable, emotionally resonant musical experience.
Featured in Rolling Stone and Westchester Magazine, Pleasantville's own Aaron David Gleason, along with Emma Freeman, and their electrifying new band, named (drum roll.....) Pleasantville, debut their release These Embers at their hometown festival album release show.
Transported to Pleasantville from their long-running residency in Greenwich Village’s Olive Tree Cafe, OTM (Olive Tree Madmen) are truly a stylistic mashup, combining a legendary ‘90’s R&B singer from Brooklyn, an Irishman who toured with The Who and Van Halen, guitar maestro Nick Cassarino (John Mayer, Trey Anastasio) with Westchester's own Craig “Butter” Glanville, and more.
Eugene Tyler Band is an award winning free-wheeling, indie-bluegrass trio, showcasing cathartic, irreverent songwriting. They've carved out an award winning unique voice in the bluegrass scene, with cutting, often humorous songs, and a fast & loose approach showcasing their bluegrass, grooving chops.
As part of our expanded family programming, The Rock and Roll Playhouse, which has hosted over 1,000 shows in venues across the US, fills the void for shared musical experiences between parents and kids: parents enjoy the music they love while little fans explore their creativity and have fun! They're first up on the Chill Tent stage with the music of Taylor Swift.
Headlining this year's festival, Dawes has cemented itself as one of the most earnest musical acts out there. A band that for fifteen years has shown it can move seamlessly between folk rock, piano ballads, and sprawling jams while maintaining both an immediately recognizable sound and a freedom from expectations. For the first time in almost a decade, founding members, brothers Taylor and Griffin Goldsmith grace the cover of a Dawes record. Oh Brother, their ninth LP, marks a distinctive new chapter for the California rock band — one that is both introspective and accessible, all while maintaining their beloved sense of sincerity.