June Events Fill Springfield Calendar

Springfield’s June calendar is packed with live music, outdoor events, Route 66 celebrations, golf and downtown art as the summer event season gets underway.

The month begins with music at The Hoogland Center for the Arts, where Springfield native Stella Cole is scheduled to perform June 3. Grateful Dub at DFV follows June 5 at Danenberger Family Vineyards, while Dexter & The Moonrocks will perform June 13 at Boondocks. Visit Springfield’s calendar also lists Scotty McCreery and Josh Turner at the Sangamon County Fair Grandstand on June 14.

Route 66 will be a major theme early in the month. The Centennial Route 66 5K is scheduled for June 6 at the Illinois State Fairgrounds’ Route 66 Experience. The race is planned as part of the 100th anniversary of Historic Route 66, with runners starting and finishing near the Gate 2 Route 66 Experience and completing part of the route on the Illinois State Fair Grandstand track.

The month will also include theater and history-focused programming. Springfield Theatre Company’s production of “For Colored Girls Who Have Considered...” is listed at The Hoogland Center for the Arts on June 12 and June 19. The Illinois State Military Museum is also scheduled to host a World War II Event on June 15.

A major downtown event arrives June 20, when the 2026 Great Race kicks off in Springfield. The Great Race is an antique, vintage and collector car road rally that will begin in Springfield before traveling Route 66 to Pasadena, California. The event is free for spectators.

Later in the month, the Memorial Health Championship, presented by LRS, returns to Panther Creek Country Club from June 22 through June 28. The tournament week includes championship golf and community events.

June wraps up with one of downtown Springfield’s most colorful annual events. SAA Paint the Street is scheduled for June 27 from 11 a.m. to 7 p.m. on Washington Street between Fourth and Eighth streets. The event gives participants the chance to paint squares along the downtown street as part of a public art celebration.

A full list of Springfield-area events can be found on the Visit Springfield events calendar at visitspringfieldillinois.com/Events?id=Upcoming.