Sleepy Hollow Music Festival 2026: Three Times Is A Charm

The Sleepy Hollow Music Festival was held Saturday, October 3, at Kingsland Point Park in Sleepy Hollow, the festival’s third year. Originally held in June, festival producers shifted this year’s gathering to October. 

When you walk into Kingsland Point Park you traverse a small bridge passing over an inlet flowing in from the Hudson River. Making your way across, you are ushered into what feels like an island of rock’n roll. 

Sleepy Hollow Music Festival 2026
Sleepy Hollow Music Festival

This “island” offered two music stages (main & regional) located at opposite ends of the space.  Vendors and a VIP area delineated the east and west boundaries while 10 bands tag teamed their performances throughout the day offering continuous live music into the night.

SoulShine: An Allman Brothers Experience
SoulShine: An Allman Brothers Experience

There were many standouts during the festival. First being the move to October. The temperate fall weather could not have been more inviting for a day of music. Second, is the park itself. Kingsland Point Park hugs the Hudson River offering a backdrop of sailboats gliding across the water while supplying a cool breeze across the park. The grounds are surrounded by tall trees reaching high into the sky creating a natural amphitheater for the show. 

Fastball
Fastball

The third, and most important, was the music. A well curated collection of performers, the lineup brought together local, regional, and national touring acts showcasing those on the cusp to artists who have solidified their status.  

Sophie B. Hawkins
Sophie B. Hawkins

Being Sleepy Hollow and in the month of October, the Halloween spirit was quite evident. Grammy-nominated singer-songwriter Sophie B. Hawkins picked up on this vibe and employed the Witches Along The Hudson, a dance ensemble garbed in full sorcerer’s attire, to help close out her set. The troupe then went on to perform their own choreographed show while casting good spells on the crowd from the main stage.  

Witches Along The Hudson
Witches Along The Hudson

New York-based SoulShine: An Allman Brothers Experience performed early in the afternoon. Comprised of two drummers, a Hammond B3 organ, dual lead guitars, bass, and vocals, the band paid homage to the pillars of southern rock, while interweaving their own inflections into the songs for good measure. 

Briarcliff School of Rock
Briarcliff School of Rock

The Regional stage stood tall and proud with bright spots at every turn. The members of the Briarcliff School of Rock did not hold back leaving it all on the stage, assuring those in question about the future of rock that it is poised and ready to take charge. Asbury Park’s Rachel Ana Dobken closed out this stage. A powerhouse on vocals and guitar, Dobken along with her band validated why she was chosen to headline.  

Rachel Ana Dobken
Rachel Ana Dobken

With the sun setting over the river, The Smithereens stepped onto the main stage. Original band members Jim Babjak and Dennis Diken were joined by guest vocalist Marshall Crenshaw and bassist Servero Jornacion for this date. Channeling the spirit of the band’s late lead singer Pat DiNizio, Babjak, Diken and crew shared songs from the band’s 46-year history including “Wall of Sleep,” “Blood and Roses,” and “A Girl Like You” confirming their standing in rock’n roll. 

The Smithereens
The Smithereens

Closing out the night, Everclear offered up 90 minutes of pure West Coast rock. Playing to a field full of enthusiastic fans, front man Art Alexakis engaged the audience throughout the set, sharing insights to the genesis of songs, life experiences, and encouraging supporting vocals from the packed crowd.  

Alexakis gave a shout out to the Smithereens, acknowledging that he owes a debt to them for inspiring him in his formative musical development. The band also paid tribute to Van Morrison’s early impact with a cover of “Brown Eyed Girl.”  

Everclear
Everclear

Everclear is rounded out by Dave French on guitar, Freddy Herrera on bass, and Brian Nolan on drums.  To bring the festival to a close, the band performed “Santa Monica” from their second album Sparkle and Fade, a fitting song that conjures images of the California coastline while performing against the banks of the Hudson River.

Everclear
Everclear

As the crowd headed back to the “mainland”, thoughts turned to who might be next year’s inhabitants of this rock’n roll refuge. If this year is an example, they will not be disappointed.   

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