3 Must-See Live Music Events in Kingston This October 2026 |
From indie folk to blues to the 16th annual O+ Festival — Kingston's October music lineup delivers something for every listener |
October in Kingston isn't just about fall foliage and Halloween — it's about live music. This month brings three distinct events that showcase the city's growing reputation as a Hudson Valley music destination, from intimate solo performances to a three-day arts festival that draws national acts.
Margaret Glaspy — October 2 at Assembly Kingston
Acclaimed singer-songwriter Margaret Glaspy brings her introspective indie folk to Assembly Kingston on Friday, October 2. The New York-based artist has built a devoted following through her self-produced recordings and sharp lyrical observations.
Glaspy's latest album, I Am Both, released in August 2026, continues her exploration of duality and contradiction. PopMatters called it "a low-key masterwork of observational wisdom, lilting melodies, and sharp wit." The record follows her 2023 album Echo The Diamond and her 2024 EP The Sun Doesn't Think, plus a 2025 covers project called The Golden Heart Protector.
Her debut album Emotions and Math earned critical acclaim for its raw honesty and intricate guitar work. At Assembly Kingston, expect an intimate evening of thoughtful songwriting and precise musicianship.
Venue: Assembly Kingston, 236 Wall Street
O+ Festival — October 9-11 at Various Kingston Venues
The 16th annual O+ Festival returns to Kingston October 9-11 with its signature blend of music, art, and wellness. This year's theme, "MO+numents," reflects the festival's commitment to creating meaningful experiences for both artists and audiences.
The 2026 lineup features Lucero, the Memphis-based rock band known for their blend of punk, country, and blues; Melissa Auf der Maur, the former Hole and Smashing Pumpkins bassist turned solo artist; and a diverse roster including Alessandra Gonzalez, Alexis Krauss (DJ set), All My Friends, The Schwegs, Wednesday Knudsen, and Whiskey Treaty Roadshow.
But O+ is more than just concerts. The three-day event includes public art installations, comedy performances, wellness workshops, and the festival's unique model: artists perform in exchange for healthcare services through O+ Clinics. It's a celebration of creativity and community that has become a Kingston fall tradition.
Venues: Various locations throughout Kingston
TAB BENOIT — October 17 at Assembly Kingston
Grammy-nominated blues guitarist TAB BENOIT brings his Louisiana roots and soulful guitar work to Assembly Kingston on Saturday, October 17. Benoit is a blues veteran who has shared stages with legends and headlined major festivals including the New Orleans Jazz & Heritage Festival.
His 2024 album I Hear Thunder marked his return to the studio after a 13-year hiatus from recording. Released on his own Whiskey Bayou Records label, the album features 10 original tracks that showcase his gritty guitar tone and authentic Louisiana blues sound. The record earned praise for its raw energy and Benoit's commanding vocals.
At Assembly Kingston, expect a high-energy performance featuring material from I Hear Thunder alongside classics from his catalog. Benoit's live shows are known for extended improvisations and his ability to make every note count.
Venue: Assembly Kingston, 236 Wall Street
A Month of Music
October 2026 offers Kingston music fans an unusually diverse lineup. Whether you're drawn to Margaret Glaspy's introspective songwriting, the multi-day celebration of O+ Festival, or TAB BENOIT's blues guitar mastery, there's something happening every weekend.
All three events highlight Kingston's emergence as a serious music destination in the Hudson Valley — a place where national touring artists choose to perform, and where local audiences show up ready to listen. |
Sep 26, 2026
3 Late October Live Music Events in Kingston NY You Can't Miss
From cult classic screenings to cello rock to Halloween cover band battles — Kingston's late October music scene has something for every taste
Sep 22, 2026
People's Place: 50 Years of Serving Kingston's Most Vulnerable Neighbors
Kingston's Community Hub for Food, Friendship, and Support Since 1970
Sep 22, 2026
Nekos-Dedrick's Pharmacy: A Kingston Institution for Generations
Kingston's oldest independent pharmacy continues to deliver personalized care with a smile
Sep 22, 2026
18th Century Autumnfest at Senate House Returns October 3-4, 2026
Step Back in Time at Kingston's Premier Revolutionary War Living History Event
3 Comments
Join the conversation
O+ is always the highlight of fall in Kingston for me. The healthcare for artists model is genuinely one of the coolest ideas any festival has come up with. Lucero headlining is a great get too, those guys put on a real show.
Joel HartwickTotally agree on the healthcare model. I have a friend who performed there a few years back and actually got dental work done through the clinics. She still talks about it. Lucero is going to be loud and sweaty in the best possible way.
Saw Tab Benoit at a festival years ago and the man absolutely does not hold back. If you have never heard him play live you are in for something. That 13 year gap between records makes this tour feel like a real event. Getting tickets before they disappear.