• Reverend Raven & the Chain Smokin' Altar Boys with Westside Andy, Monday, July 27, Maple Bluff Beach, 6 p.m.: Now that the wildfire smoke is apparently giving us a break, do take advantage of an outdoor concert. In the shadow of the Maple Bluff Country Club with a view of Madison’s skyline, a stone’s throw from the governor’s Executive Residence, kick back to the blues with Milwaukee’s Reverend Raven & the Chain Smokin' Altar Boys with Madison harmonica legend Westside Andy. Note: Maple Bluff's annual Fourth of July fireworks display, postponed earlier this month, was initially rescheduled to follow this concert, but is again postponed.

• The Great Gatsby, July 28-Aug. 2, Overture Hall: F. Scott Fitzgerald’s classic novel The Great Gatsby arrives reborn with the full Broadway treatment as a musical promising some jazz-age shimmer to enliven the tragic tale. The score by Jason Howland and Nathan Tysen blends jazz and pop, which feels right for a story forever caught between elegance and a hangover. Performances at 7:30 p.m. July 28-31, 2 and 7:30 p.m. Aug. 1 and 1 and 6:30 p.m., Aug. 2. Tickets at overture.org.
• Nick Martino + Patrycja Humienik, Tuesday, July 28, A Room Of One’s Own, 6 p.m.: Milwaukee native Nick Martino will read from his debut poetry collection, Scrap Book, joined by Madison author and editor Patrycja Humienik. Martino explores his father’s incarceration and how its impacts rippled through generations; poems describing Polaroid photos of his father in prison accompany excerpts from his mother’s journal at the time of her husband’s jailing, where she wrote about prison visits alongside her observations of Lake Michigan.

• CANCELED: Concerts on the Square, Wednesdays, through July 29, Capitol Square, 7 p.m.: The Wisconsin Chamber Orchestra’s annual summer Concerts on the Square season continues every Wednesday in July, and you can save your spot on the lawn with a blanket starting at 3 p.m.; the concerts take place on the King Street corner. The final concert July 29 focuses on works by guest pianist Stewart Goodyear. In case the weather looks sketchy, a rain call will be made by 3 p.m. July 27 update from WCO: "The Wisconsin Chamber Orchestra (WCO) has made the difficult decision to cancel this Wednesday's Concerts on the Square performance on July 29, 2026.The decision comes as Madison continues to grieve following the fatal police shooting of Corey Durell Ruiz on July 22, 2026. In conversations with community stakeholders, it has become clear that this is a time for listening, reflection, and creating space for our community to process together."
• West Texas Exiles, Wednesday, July 29, The Bur Oak, 8 p.m.: Texas. Well, it’s okay, these guys are from Austin, the Madison of the southwest. Their tunes range from melodic folky Americana to good ol' Texas honky-tonkin', and members Marco Gutierrez, Daniel Davis and Colin Gilmore (son of Jimmy Dale Gilmore) share songwriting and trade off on lead vocals. Any of them can sound like a less tormented Jason Isbell. The band released its first full length album, 8000 Days, in 2025. Tickets at theburoakmadison.com.

• Art Paul Schlosser, through July 31, Mother Fool’s Coffeehouse: If you’ve spent any time on State Street in the last several decades, you’ve likely stopped to check in on what stream-of-consciousness singer-songwriter Art Paul Schlosser is up to while busking. Schlosser has become as prolific at visual art as songwriting, and a collection of paintings of “Famous Celebrities” can be viewed at Mother Fool’s in July. (Also: A second series of summer-themed paintings can be found from July 10-Aug. 31 at Madison Senior Center.)
• Through the Keyhole and the Storm, July 30-Aug 1, Common Wealth Gallery, 6:30-9 p.m.: Liz Sexe Dance blends film and movement in its latest creation, Through the Keyhole and the Storm. Environments include spaces filled with keyholes to peek through and a space filled with plastic; these can be explored from 6:30-9 p.m., and each night live dance performances at 7:30 p.m. include a solo work by Sexe and a “storm” of dancers Erin Alberts, Abby Frank Taylor, Eve Levi, Tara McAninch and Megan Schimke immersing the audience. Find more info at lizsexedance.com.

• Caveman Play, July 30-Aug. 9, The Crossing: A turning point in civilization receives a comedic do-over in Caveman Play. Savannah Reich imagines a moment humanity could trade hunting and gathering for agriculture — as a sales pitch delivered by two eager cave-people and their domesticated tiger. It's a wonderfully offbeat premise that quickly snowballs into big picture questions about modern-day problems, with just the right amount of weird. To add a touch of unpredictability the show's six actors draw their roles from a hat before every performance, so neither they nor the audience know who's playing whom until the lights come up. Performances, at 1127 University Ave., are at 7 p.m. Thursday-Saturday (except 6 p.m. on Aug. 8) and 2 p.m. Sunday; reserve a seat here.
• Andrew Dismukes, July 30-Aug. 1, Comedy on State: Comedian and actor Andrew Dismukes joined Saturday Night Live as a writer in 2017, and has been a repertory cast member since 2022. On the show he’s proven one of the cast’s most versatile players, with a keen sense of comic timing. Dismukes is visiting a few cities on a stand-up tour this summer, including this weekend run at Comedy on State, at 7 p.m. July 30 and 7 and 9:30 p.m. July 31-Aug. 1. Tickets at madisoncomedy.com.

Find the individual Picks collected here, and as part of the full calendar of events.

Editor's note: This post has been updated to reflect the cancellation of Concerts on the Square.