Recently, Alpine Valley Music Theatre had posted on social media that their 2025 calendar was defrosting. On Monday morning, they might as well have taken a blowtorch to it, with a major concert announcement. 

On Friday, September 19th, the 10th anniversary of the Outlaw Music Festival tour will come to East Troy, with a stacked lineup that includes legends Bob Dylan, Willie Nelson and Sheryl Crow, as well as rising Americana acts Waxahatchee and Madeline Edwards. Crow appeared on Sunday night’s GRAMMYs broadcast, playing bass with Dawes for the opening cover of Randy Newman’s “I Love L.A.” to pay tribute to the victims of the recent California wildfires.

The five-act concert is part of the nationwide 10th anniversary tour, which will see more than 23 acts play select dates throughout the course of the summer. Among the larger lineup of announced names are Turnpike Troubadours, The Avett Brothers, and Charles Wesley Godwin, all of which have already been announced for either dates at Summerfest or the 2025 Harley Homecoming festival.

The festival first played the Milwaukee area in 2017 at the American Family Insurance Amphitheater. Since then, it has been a part of Summerfest in 2019, before moving to Alpine Valley in 2023. It also played the Somerset Amphitheater in 2023 and 2024.

Tickets for the Outlaw Music Festival go on sale to the general public on Friday, February 7th via Live Nation. A Citi cardholder presale will take place beginning on Tuesday at 10 a.m. as well, ending on Thursday. 

Check out all of the major outdoor shows happening in Milwaukee this summer here.

There are tons of concerts happening throughout Milwaukee almost nightly, so stay tuned to OnMilwaukee for more concert announcements and check out our monthly music guide to see where you can check out a gig tonight.