Chicago, IL|October 12th, 2026
Photographed and Written by River Epperson
The Milwaukee musician showcases her debut record and brings folk-rock across the Midwest with the Stay Soft tour.
“Free Monday” has become a beloved phrase among lovers of Chicago’s local music scene. For over two decades, the historic venue has hosted what it calls “Free Mondays”: free live music every week with no cover. Over the years, the Empty Bottle has serves as an early home for countless artists in Chicago, including Wet Leg, The Black Keys, The Namby Pamby, and more. Since the early 2000s, Free Mondays have given Chicago’s concertgoers a chance to discover new independent music, from acts both local and out of town. While Mondays may be another bar’s slowest day of the week, Empty Bottle’s performance venue was crowded and the air thick with anticipation for Ellie Jackson on Monday, October 12.
Presented by Shucks Touring, an indie tour management company founded by Payton Knerr, Ellie Jackson rolled through Chicago promoting her debut record Stay Soft (Book Club). The record, released October 1, 2026, highlights Jackson’s distinct folk-rock sound and smooth vocals. The crowd was clearly taken with Jackson and her band, cheering them on throughout the set. Many audience members were surprised to discover Jackson was touring her debut record and was not a more established musician. Hailing from Milwaukee, Jackson’s (guitar/vocals) band is filled by Caley Conway (guitar/backing vocals), Barry Paul Clark (bass), and Devin Drobka (drums), and Monday’s show featured support from Chicago’s Mass and Old Pup, both providing solo sets of ambient music.
The Stay Soft tour, presented by Shucks Touring, began 10/3 in Sturgeon Bay, WI, and continues until 10/24, when it concludes at Fort Wayne, Indiana’s Brass Rail. Local openers support Jackson and company on the road. Stay Soft, Jackson’s debut record, is available for listening on all streaming platforms and for purchase on Bandcamp. Shucks Touring, founded in 2026 by Payton Knerr (The Namby Pamby), has more artists on the road, including Josephine and Mol Sullivan.
