While Trapper Schoepp spends much of each year on the road and has found fans all over the world, the tireless Milwaukee troubadour makes sure to regularly pay homage to Wisconsin in his work. In recent years, he’s helped Bob Dylan finish a song about the state, and has written his own songs about local legends like Lawrencia “Laurie” Bembenek, Kate Blood, and 7 Mile Fair.

Schoepp is currently in California working on a record with acclaimed musician and producer Mike Viola, but before leaving town, he made sure to stop by another Wisconsin sensation. Of course, we’re referring to that gigantic sinkhole that recently opened up in Whitefish Bay. The suburban chasm is currently fenced off as crews work to fill it in, so naturally, Schoepp decided to play some songs near it.

With the help of local videographer Nels Lindquist, Schoepp recently released three videos he’s calling “The Sinkhole Sessions.” The videos feature Schoepp playing acoustically in and around the sinkhole.”I think it’s my Milwaukee ‘jump the shark’ moment, but in the best way possible,” Schoepp tells Milwaukee Record.

Check out his live rendition of The Velvet Underground’s “I’m Waiting For The Man” as city workers look on.

Subsequent “Sinkhole Sessions” include a performance of his 2023 song “Diocese” in front of a fallen tree.

And a version of Hank Williams’ famed “Lost Highway” in front of one of the planet’s largest sinkholes…Lake Michigan.

Speaking of Trapper Schoepp performances near Lake Michigan, he’ll be returning to town to play a free show at Bradford Beach on July 10 as part of the new ArtBlaze On The Beach series. His performance will take place 3:30-4:30 p.m.

About The Author

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Co-Founder and Editor

Before co-founding Milwaukee Record, Tyler Maas wrote for virtually every Milwaukee publication (except Wassup! Magazine). He lives in Bay View and enjoys both stuff and things.