2025 Outlaw Music Festival Tour, A Milestone Year Built On Family

The 2025 Outlaw Music Festival Tour came to a powerful close on September 19th at Alpine Valley Music Theatre in East Troy, Wisconsin, wrapping up a landmark 10th anniversary tour that crisscrossed the country all summer long.

Alpine Valley was the perfect final chapter, an electric night that captured the gratitude and connection built over the course of the tour. Willie Nelson & Family, Bob Dylan, Sheryl Crow, Waxahatchee, and Madeline Edwards gave unforgettable performances. From Dylan’s captivating set to Sheryl Crow’s radiant energy, with Willie Nelson bringing his unmistakable joy to the stage and reminding everyone why the Outlaw Music Festival has become such a beloved tradition.

The journey was widely chronicled in the press, with Rolling Stone highlighting the excitement from the moment the tour was announced to their in-depth reviews of the performances themselves. Their coverage captured the scope of the festival and the unique spirit that defined this anniversary year.

But none of it would have been possible without the fans. Thousands came together in cities across the country, singing, dancing, and sharing in a collective experience that felt both timeless and deeply of the moment. For fans who want to relive the memories, our photo gallery from the tour showcases some of the most iconic moments, and the Outlaw Music Festival online shop still offers official merchandise—from t-shirts and hoodies to posters and more—to commemorate an incredible season.

As the lights dimmed at Alpine Valley, one thing was clear: the 2025 Outlaw Music Festival was more than just a tour—it was a milestone year built on music, gratitude, and the unshakable bond between artists and fans.