5 Live Music Events in Kingston, NY This October 2026

October in Kingston isn't just about fall foliage and apple cider — it's one of the busiest months for live music in the Hudson Valley. The crown jewel is Assembly, Kingston's premier concert venue in the historic Uptown/Stockade District, which has packed its calendar with an eclectic mix of indie rock, Americana, blues, and community festival energy. Here are five live music events you won't want to miss this October.

1. Start Making Sense: Talking Heads Tribute with Groove Merchants

Kick off the month with one of the most acclaimed Talking Heads tribute shows touring the country. Start Making Sense brings the full theatrical spectacle of the legendary Stop Making Sense concert film to life, backed by the Groove Merchants band. Expect "Once in a Lifetime," "Psycho Killer," and "Burning Down the House" performed with the energy and artistry that made Talking Heads one of the most innovative bands in rock history.

2. Margaret Glaspy

Brooklyn-born singer-songwriter Margaret Glaspy has been turning heads with her razor-sharp guitar work and genre-defying songwriting. Her 2024 album Devotion earned widespread critical acclaim, blending indie rock, folk, and raw emotional power into something entirely her own. This intimate Assembly show is a chance to catch her on a smaller stage before she outgrows rooms like this.

3. Angelo De Augustine with Erin Rae

Singer-songwriter Angelo De Augustine brings his introspective, folk-tinged indie rock to Assembly with special guest Erin Rae. De Augustine's music — often compared to Sufjan Stevens and Elliott Smith — is built on delicate fingerpicking, confessional lyrics, and a quiet intensity that fills a room. Erin Rae, a Nashville-based artist known for her jangly power-pop and sharp lyricism, is the perfect opener for this midweek treat.

4. O+ Festival Featuring Lucero, Skorts, and Alexis Krauss DJ Set

The annual O+ Festival returns to Kingston for a full day of music, art, and community at Assembly. This year's lineup is stacked: Memphis rock legends Lucero bring their signature blend of punk, country, and soul; indie rockers Skorts deliver high-energy garage rock; Alexis Krauss (of Sleigh Bells) spins a DJ set; and the bill rounds out with Nathan Meltz, The Jaguar, Alessandra Gonzalez, and Eric EQ's dance party. O+ is more than a concert — it's a Kingston tradition celebrating music, wellness, and creativity.

5. Tab Benoit with Ghalia Volt

Louisiana swamp blues guitarist Tab Benoit is a living legend of American roots music. With over 30 years of soul-drenched guitar and songwriting, Benoit has shared stages with everyone from Buddy Guy to Willie Nelson while remaining fiercely rooted in the bayou blues tradition. Opening for him is Ghalia Volt, a rising force in blues-rock who brings raw power and vintage swagger to every performance. This is the show to bring your blues-loving friends to.

Plan Your October in Kingston

All five events take place at Assembly, Kingston's premier live music venue located at 236 Wall Street in the historic Uptown/Stockade District. The venue features a no-fee box office open Mondays from 4–6 PM, and tickets are available online through Tixr and Impact Concerts. With shows spanning indie rock, folk, blues, tribute acts, and community festivals, October 2026 is shaping up to be one of Kingston's best months for live music yet.