Entertainment events in Highland

Check out happening entertainment events all around Highland, IL

Madison County Fair

Tue, 21 Jul at 09:00 am 2025 Park Hill Dr, Highland, IL, United States, Illinois 62249

Spring Artisan Market

 Sat, 25 Apr at 10:00 am 12760 Troxler Ave, Highland, IL

Highland's Got Talent at Color and Sound City Wide Celebration

 Sat, 02 May at 01:30 pm Highland Square

PBJ Festival - June 19th

 Fri, 19 Jun at 11:30 am Highland Square

Kirchenfest 2026 with Shut Up Mark!

 Sat, 22 Aug at 08:00 pm Kirchenfest

PBJ Festival - July 10th

 Fri, 10 Jul at 11:30 am Highland Square

Mind-Blown: A Comedy Magic Show @ Big O's Sports Bar

 Sat, 19 Sep at 08:00 pm Big O's Sports Bar & Restaurant USD 23

Frozen the Musical presented by Highland High School

 Fri, 24 Apr at 07:00 pm Highland Elementary Auditorium

PBJ Festival - July 17th

 Fri, 17 Jul at 11:30 am Highland Square

Mind-Blown: A Comedy Magic Show @ Big O's Sports Bar

 Sat, 11 Jul at 08:00 pm Big O's Sports Bar & Restaurant USD 23

Mind-Blown: A Night of Comedy & Magic

 Sat, 09 May at 08:00 pm Big O's Sports Bar & Restaurant USD 23

ELT’s Performing at The Corner Keg!!

 Sat, 16 May at 09:00 pm Corner Keg

Next Stop Comedy at Big O's Sports Bar! - Highland, IL

 Sat, 18 Oct at 08:00 pm 907 Main St USD 28

Pop Up Party!

 Fri, 29 May at 10:00 am 810 and 808 Broadway, Highland, IL

THE GREENHOUSE FLORIST & GIFT SHOP with TGNY ACOUSTIC

 Fri, 31 Jul at 05:00 pm The Greenhouse Florist & Gift Shop