Music
2026 Headliner Bellamy Brothers
Each year, Old Town Street Festival offers a diverse array of musical talent for all to enjoy. Festival performances are free to attend.
Featured Music
Bellamy Brothers
Howard and David continue to prove that the trail they’ve ridden to fame has been as unique as their music itself—music that celebrates 50 years of success in 2025.
The road that started on the pop music charts in the ‘70’s, took a winding turn into country music in the ‘80’s, paving the way for duos to come, such as Brooks & Dunn, Montgomery Gentry, Big & Rich and previously—The Judds. But before the road forked into country, the musical odyssey of brothers Bellamy started creatively smoldering in their home state of Florida, before exploding nationally amidst the ’70’s pop music culture of L.A.
The Bellamy Brothers will perform on the Old Town Grandstand live at 7:30pm.
Get VIP tickets Here!
General admission is free to all. VIP tickets near the stage with seating and shade available for a fee.
Other Music
Boot Rock Boys
Meet the Boot Rock Boys, a dynamic group of musicians who redefine your favorite classic tunes with a unique twist. They are a lively stage filled with infectious energy, where awesome vocals and rich harmonies collide with the sweet sounds of a mandolin, a crying steel guitar, a blazing fiddle, and a smoking hot guitar. It’s not just music; it’s an experience that will have you tapping your feet and singing along in no time.
Performing 12-3pm live on the Old Town Grandstand.
Steph Cash
Steph Cash is a singer/songwriter born and raised in Virginia. Cash is currently based in Austin, TX, but spent a lot of time in the Blue Ridge Mountains of Virginia, where she learned about country music. When it comes to writing songs, Cash brings the sounds of true Texas honky tonk music with a country outlaw twist to her listener’s ears. Cash began breaking into the Texas Country Music scene in 2022 with a full band behind her. Cash and her band recorded and released a few singles in 2022, to include “Country Music” before releasing a full album in January of 2023 titled “Where I’ve Been”. Since then, Cash has put out additional singles with plans to record a sophomore album in 2025.
Performing 3-6pm live on the Old Town Grandstand.
Old Town Leander 