The 20th anniversary of Reggie’s Sleepout, a fundraiser organized by the Iowa Homeless Youth Centers, will take place Nov. 1 at Drake Stadium. The overnight event invites participants to sleep outdoors in tents, boxes, or sleeping bags to raise awareness and money for critical services, including shelter, counseling, and education to combat youth homelessness. The organization hopes to raise $500,000 this year with proceeds going directly to statewide programs. The evening will also feature a “best shelter” contest for individuals, schools, and business teams, with materials provided by Homemakers Furniture.