November 8, 2025 | 7:00 pm

Leroy Preston

Founding member of the Grammy Award–winning western swing group Asleep at the Wheel, Leroy Preston brings a vibrant mix of swing, honky-tonk country, and jazzy blues to the stage.A Vermont native, Preston launched his...
[SEE DETAILS BELOW]
Visit Event Website
Rossignol - Boots - 728x90
Vermont-Vibes-Time-to-Book-It-Pet-Friendly-Log-Cabin

Founding member of the Grammy Award–winning western swing group Asleep at the Wheel, Leroy Preston brings a vibrant mix of swing, honky-tonk country, and jazzy blues to the stage.

A Vermont native, Preston launched his career locally before co-founding Asleep at the Wheel, touring and recording with the band to international acclaim. He later moved to Nashville, where he built a prolific songwriting career. His credits include Rosanne Cash’s #1 hit “My Baby Thinks He’s a Train”, along with top-charting songs for Asleep at the Wheel, k.d. lang, and Lee Roy Parnell.

His co-writing collaborations span Los Lobos, Marshall Crenshaw, Rosie Flores, Robert Earl Keen, and many more artists who have recorded his material. After a long hiatus, Preston has returned with new songs and a stellar lineup of musicians on The Vermont Sessions, released in November 2024.

Where to stay

BOOK DIRECT IN VERMONT This Fall: 
FEWER FEES, Better VIBES

Ditch the big booking engines and tap into Vermont’s best-kept stays - direct from the source. Our new guide delivers unique rentals, mountain cabins, cozy cottages, and one-of-a-kind homes you won’t find anywhere else. Skip the fees, support locals, and stay somewhere that actually feels like Vermont.
Sponsored by Vermont.com
Check it out
Wilburton-Destination-Resort-Arial-Fall-Foliage-of-Pool-and-Mansion
Where To Stay

BOOK DIRECT IN VERMONT This Fall:
FEWER FEES, Better VIBES

Ditch the big booking engines and tap into Vermont’s best-kept stays - direct from the source. Our new guide delivers unique rentals, mountain cabins, cozy cottages, and one-of-a-kind homes you won’t find anywhere else. Skip the fees, support locals, and stay somewhere that actually feels like Vermont.
Sponsored by Vermont.com
Check It Out
Sign Up For 2025 Foliage Updates
New Newsletter Signup

Featured Events

View All
map-markerscreenmagnifier