The 2026 Pleasantville Music Festival was held July 11, 2026, at Parkway Field in Pleasantville, NY. Incorporating three stages, fourteen acts, food, vendors, rides and games, the festival made sure there was something for everyone.
This year saw the return of Bruce Figler as director of the festival after a one-year absence. Figler spoke candidly during the day of the complexities in producing an event of this magnitude while continuously giving shoutouts to the various agencies and volunteers of the village of Pleasantville for their enormous support to ensure the festival’s success.
This year’s festival started at the Chill Tent stage: a large circus-style tent tucked in the back of Parkway Field. With rows and rows of seats and its perimeter surrounded by industrial-size fans circulating a cool breeze under the canvas, this was the place to “chill” on a hot July day and listen to music.
Opener Robert “The Guitar Guy” brought percussion instruments for young future musicians to join in and jam with him as he played acoustic guitar and sang songs these preschoolers’ parents have in their collections. With the future of rock secured, the Chill Tent stepped into country mode with the Hudson Valley’s Way Behind The Sun. Performing as a duo, this husband-and-wife combo glowed as they shared songs of the trials and tribulations of life as musical performers.
Grammy-nominated singer/songwriter and Bronx native Ari Hest took the middle slot, delivering a powerful solo performance. Dream Street, who were young teens breaking into showbiz in 1999, followed, serving up a reignited and inspired 2026 acoustic/electric set.
To close this portion of the festival, the Chill Tent was blessed with a second Grammy nominee, Yola. The crowd erupted into cheers as soon as she and her band walked on stage. Yola’s voice, joined by two backup singers, guitar and keyboards, reverberated through the open air of the tent, leaving everyone longing for more.
The Pamnation Party stage has proven to be an alt/indie rockers’ oasis over its many years of stage sponsorship at the festival. This year was no exception. Similar Kind from Norwalk, CT, opened with their fun pop groove to get things going. Brooklyn’s Two-Man Giant Squid, who are more than just two men, brought a punk/space sound resonating through the crowd with dancing breaking out as a result.
Jam band fans were living large when Round Trip, featuring Lara Cwass, stepped up to play. Guitarists Jake Stevenson and Lara Cwass locked in as they traded leads throughout their time on stage. Bass player Drake Millhausen and drummer Walker Macmillan supplied a syncopated foundation, letting the band dig deep into improvisation and take their musical experimentation to the next level. The Thing from Brooklyn, closed out the Pamnation Party stage. The band supplied a garage/rock/psych groove, giving a potent performance and setting up the night for the festival’s headliner.
The Speakers started off the Main Stage. The band, based in Elmsford, is a collection of adult musicians with disabilities. While each faces their own personal challenges, when the music started they were a rock’n roll band.
The Vindys from Ohio were in the second slot. This big band with a big sound took control of the stage. Lead singer Jackie Popovec strutted across the boards while steering the band with her powerful vocals. Their standout set definitely garnered them some new followers.
Perennial favorites, The Fixx shared “One Thing Leads to Another” and “Saved by Zero,” along with others from their vast catalog. Alt-country rockers Old 97’s from Dallas, TX, did what they do best: playing rock tunes that make you want to move your feet, sharing songs from their thirteen full length releases and adding in Merle Haggard’s “Mama Tried” for good measure.
Festival headliners OK Go proved to be the icing on the cake for this year’s festival. Mid-show, lead singer Damian Kulash took to an impromptu stage in the middle of the field with acoustic guitar to perform “This Is How It Ends” to a jubilant crowd. This four-piece band did not hold back during an hour-long set, sharing fourteen songs including “Shooting the Moon” on hand bells and closing the night with “Here It Goes Again.”
With a triad of performance spaces offering a wide spectrum of musical idioms, each stage could have stood alone on its own merits for a festival. For those attending, the challenge was to experience them all. Achieving twenty years as a festival is an incredible milestone. With the depth of entertainers and the logistics required behind the scenes, it takes more than a few people to make this happen. It takes a village
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