After the park flooded during a festival weekend, the organizers moved the festival first to Stone Mountain Events Center in Dripping Springs, Texas, and later to the Salt Lick BBQ Pavilion and Camp Ben McCulloch in Driftwood, Texas.

In 2018, the festival moved to its permanent home on 145 acres it purchased in Tilmon (though the mailing address is Dale, Texas), between Austin and San Antonio.

Old Settler's has been recognized for its contribution to Central Texas culture; with over 30 bands performing for 16,000 roots-music fans each year, it is among several major events that help the region sustain its status as the “live music capital of the world.” When the festival moved to its permanent property, the Austin American-Statesman noted, "OSMF has become an elite musical event without sacrificing the community vibe that built it.

The Old Settler's Music Festival's Youth Talent Competition has been held since 2002.

The contest encourages young roots musicians to develop their talents by offering cash awards, scholarships, a performance slot at the following year's festival, mentoring and recognition.