Jessica Lynn plays piano, guitar, harmonica, and drums — not as separate features but as the natural vocabulary of a set that refuses to stay in one place. On Halloween night at Daryl’s House in Pawling, that restlessness becomes the whole show: her annual Halloween Bash is built around a promise to take the room on a trip through favorite hits from every genre, which turns out to be more literal than promotional when the artist making it can reach for several different instruments in a single evening, and has 22 charting releases across 22 countries to give the genre-hopping some weight.
About the Show
Lynn’s Halloween Bash at Daryl’s House has become one of the Hudson Valley’s more reliable autumn traditions. This year’s edition holds to what’s worked: costumes are strongly encouraged, the night includes games and dancing, and the costume contest with Daryl’s House Club prizes remains a focal point. The show is all ages.
Behind the celebration, there is serious music. Lynn’s most recent album, All I Own, released January 17, 2025, hit number one on the digital country charts in the United States and the United Kingdom and reached number two across all genres. The record draws on rock, country, blues, and Latin influences, and it was made under real duress: after sinus surgery, Lynn developed muscle tension dysphonia and recorded in ten-minute vocal bursts to work around the damage. She has earned her place — two nationwide television concert specials (Jessica Lynn – This Much Fun and Jessica Lynn – Takin’ Over), stages shared with Brad Paisley, Keith Urban, ZZ Top, and Loretta Lynn, and an international following built through years of road work across 14 or more countries. She has been described as “a rocket force, paving her own way as a unique face and voice in modern country music.”
Lynn performs with her family band: father Peter Calamera on bass, mother Victoria Calamera on background vocals, husband Steve Sterlacci on lead guitar. The trust that builds in that kind of ensemble is audible from the first song.
Venue & Logistics
Daryl’s House is a 300-capacity club on Route 22 in Pawling, a room in the Hudson Valley that draws artists who want to be heard rather than amplified into the rafters. Doors open at 5:00 p.m.; the show starts at 8:00 p.m.
Tickets
Tickets range from $33.84 to $45.17. Buy tickets