Summer Park Jam

TRUE Skool is bringing Hip Hop legends Yo-Yo, Rah Digga, Sweet Tee, and Da Odd Couple to headline Milwaukee’s 2026 Summer Park Jam Weekend. The free two-day event includes Friday’s CEO Sessions featuring Crash Dummies Mike & Pat, DJ Rob Swift, and Jene Tate, followed by Saturday’s all-ages festival with live performances, local vendors, breakdancing & graffiti battles, food trucks, and more.

It’s a major moment for downtown Milwaukee, celebrating Hip Hop legacy, culture, and community!

Friday, August 14 – 12pm-4pm (Arrive by 1PM)
Inside Marcus Performing Arts Center | Free with Reservation 

CEO Sessions brings together industry leaders and Hip Hop innovators for conversations designed to share real-world strategies for building, growing, and monetizing creative businesses.

Crash Dummies Mike & Pat will break down how to launch, scale, and aggressively monetize your podcast. DJ Rob Swift, founding member of The X-Ecutioners, will share knowledge from his latest book, City of Hip-Hop. Jene Tate of Unfinished Legacy will discuss brand building and the process of establishing a successful storefront.

Saturday, August 15 – 12pm-8pm
Peck Pavilion, MPAC Outdoor Grounds | Free and Family-Friendly 

HIP HOP LEGENDS IN MILWAUKEE! Yo-Yo, Rah Digga, Sweet Tee, and Da Odd Couple are bringing the heat to Summer Park Jam! Enjoy food trucks, a car show, a local vendor market, a children’s area for families, and non-stop dancing at the Open DJ Tent. It’s an ALL DAY JAM from Noon–8 PM! FREE & FAMILY FRIENDLY! Full performer lineup announcements coming soon!

This event is presented by True Skool, an independent organization separate from the Marcus Performing Arts Center.