Ramblin’ Roads Country Fest Brings a Full Day of Country Music and Community to Southern Vermont
Winhall, VT — Ramblin’ Roads Country Fest will make its Vermont debut at the Bondville Fairgrounds on Saturday, October 3, bringing a full day of live country music, local food, vendors, family activities and community to Southern Vermont.
Presented by Ramblin’ Roads Entertainment LLC, the festival was created with a simple goal: to bring people together while giving regional artists and small businesses a place to be seen, heard and supported.
Music will run from noon to 9 p.m. across two stages, featuring country, Americana and singer-songwriter talent from throughout New England.
Nick Bosse & The Northern Roots will headline the festival, joined by a diverse lineup of regional performers including Jason Ingriselli & The Miles North, Jordan Gladu Band, Charlie Diamond Band and Vermont singer-songwriter Shaely O’Dou. The day will also feature an intimate songwriters round highlighting original music from regional songwriters.
Beyond the music, festivalgoers can explore local artisan and craft vendors, enjoy a variety of food options and visit a dedicated Kids Zone. The event is designed as an all-ages fall gathering where families, music fans, artists and local businesses can spend the day together.
Set at the historic Bondville Fairgrounds during one of Southern Vermont’s most beautiful times of year, Ramblin’ Roads Country Fest hopes to grow into an annual tradition rooted in Country. Community. Connection.
Gates open at 11:30 a.m., with music beginning at noon and continuing until 9 p.m. Admission is $25, children 13 and under are free, and parking is free. The rain date is Sunday, October 4.
EVENT DETAILS
Ramblin’ Roads Country Fest
Saturday, October 3, 2026
Gates: 11:30 a.m. | Music: 12–9 p.m.
Bondville Fairgrounds
30 VT Route 30, Winhall, Vermont
Rain Date: Sunday, October 4
Tickets: $25 | Ages 13 & under free | Free parking
Festival information, tickets and the complete lineup are available at ramblinroadsentertainment.com.
MEDIA CONTACT
Mary-Jane O’Dou
hello@
Ramblin’ Roads Entertainment LLC
Country • Community • Connection
Organizer of the Ramblin’ Roads Country Fest