Join us for live music throughout the winter season at The Gambit Bar, featuring talented local artists every night of the week. Enjoy great food, artfully crafted cocktails, and the relaxed, social vibe that makes après at The Sebastian – Vail truly special.
Music Schedule
Monday – Andy Cyphert | 6–9 PM
Tuesday – Nick Steingart | 6–9 PM
Wednesday – Brendan McKinney | 6–9 PM
Thursday – Jason Gregg | 4–6:30 PM | Ben Koelker | 7:30–10 PM
Friday – Brian Spotts | 4–6:30 PM | Tim & Taylor | 7:30–10 PM
Saturday – Diego Espinoza | 4–6:30 PM | Chris Maggini | 7:30–10 PM
Sunday – Al Maul | 4–6:30 PM | Michelle Levy | 7:30–10 PM
Meet the Artists
Andy Cyphert – Mondays
A six-time Vail Daily “Best Local Musician,” Andy brings soulful guitar and vocals spanning rock, blues, and country—setting the perfect tone for a laid-back evening in the mountains.
Nick Steingart – Tuesdays
Nick blends folk, rock, and Americana with looping guitar and vocals, creating rich, layered performances that capture the heart of Colorado’s mountain music scene.
Brendan McKinney – Wednesdays
A Vail favorite for over 15 years, Brendan delivers powerful vocals, masterful guitar, and a mix of originals and Americana covers that always connect with the crowd.
Jason Gregg – Thursdays (Early Set)
Jason’s acoustic sets mix classic rock favorites and original songs, all performed with warmth, soul, and easy-going après energy.
Ben Koelker – Thursdays (Late Set)
Longtime local Ben Koelker brings decades of experience and a sound rooted in rock, bluegrass, and Americana—perfect for winding down or singing along.
Brian Spotts – Fridays (Early Set)
Brian’s upbeat acoustic performances feature favorite singalongs from the ’90s to today—easygoing, familiar, and always fun.
Tim & Taylor – Fridays (Late Set)
This country duo combines heartfelt harmonies and lively storytelling, blending modern hits with timeless charm and energy.
Diego Espinoza – Saturdays (Early Set)
A master of world sounds, Diego fuses Spanish guitar, Latin rhythms, and jazz for an elegant, soulful start to your evening.
Chris Maggini – Saturdays (Late Set)
Chris brings classic rock, country, and pop favorites to life with his guitar, harmonica, and signature “campfire” style.
Al Maul – Sundays (Early Set)
With rugged mountain roots and soulful vocals, Al’s acoustic performances capture the spirit of the West and the beauty of Vail Valley.
Michelle Levy – Sundays (Late Set)
Michelle closes out the week with powerhouse vocals and a fun, high-energy mix of rock, pop, and crowd favorites that get everyone singing along.
Also check out other Music events in Vail, Entertainment events in Vail.
