Upcoming Highland Events

Check out what's happening all around Highland, IL

Kirchenfest 2026

 Fri, 21 Aug at 05:00 pm 1412 9th St, Highland, IL, United States, Illinois 62249

B&B & Schweizerfest

Sat, 13 Jun at 08:00 pm Highland Square

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

St. Paul Strassenlauf 2K, 5K, 10K

 Sat, 22 Aug at 07:30 am St. Paul Catholic Church Highland

PBJ Festival - July 10th

 Fri, 10 Jul at 11:30 am Highland Square

The Yacht Rockers at Olde Wicks

 Thu, 21 May at 07:00 pm 1100 5th Street, Highland, IL, United States, Illinois 62249

90's Trivia Night hosted by Highland Community Closet

 Sun, 12 Apr at 07:00 pm Big O's Sports Bar Highland Square IL

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

Street Art Festival

 Sat, 19 Sep at 03:00 pm Highland Square

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

4th Annual Joshua Melton memorial

Sat, 18 Jul at 05:00 pm Highland Speedway

Hydrants, Hoses and Heroes 5K

 Sat, 02 May at 08:00 am Lindendale Park

Dairy Day at the Madison County Fairgrounds!

 Sat, 16 May at 10:00 am Madison County Fairgrounds

Sparky & Pop Explore the Square 🦆 Pop’s Duck Rescue Mission

 Sat, 09 May at 10:00 am Highland Square

A Night of Stars Gala

 Sat, 25 Apr at 06:00 pm 2005 Park Hill Drive Highland, IL 62249

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

Spring Shop Hop

 Sat, 16 May at 10:00 am 1008 Laurel St, Highland, IL 62249-1504, United States

Highland Band and Choir Artisan Market

 Sat, 25 Apr at 10:00 am 12760 Troxler Ave, Highland, IL 62249-1044, United States

HIGHLAND VFW GLO-BINGO

 Sat, 02 May at 06:00 pm VFW Post 5694

EvUCC - Vacation Bible School (VBS)

 Mon, 01 Jun at 09:00 am 2520 Poplar St, Highland, IL, United States, Illinois 62249

Plant Sale

 Fri, 01 May at 11:30 am 12760 Troxler Ave, Highland, IL 62249-1044, United States

2026 Annual Awards Dinner

 Thu, 25 Jun at 05:00 pm Highland Knights of Columbus Council 1580

Glow Golf Fundraiser

 Fri, 08 May at 06:00 pm Country Club Rd, Highland, IL 62249, United States

BnB @ Madison County Fair

 Fri, 24 Jul at 08:00 pm Madison County Fairgrounds

Mind-Blown: A Night of Comedy & Magic

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

Highland Garden Club Plant Sale

 Sat, 09 May at 08:00 am Korte Rec Center

Boot Camp Pop Up with Ashley

 Sat, 04 Apr at 08:00 am Korte Rec Center

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

Amanda Wick @ The Greenhouse ❀

 Fri, 01 May at 05:00 pm The Greenhouse Florist & Gift Shop

Business After Hours

 Thu, 16 Apr at 05:00 pm Highland Liquor & Food Mart by TL&G

Sunday Funday! Jesse & Alex at Schweitzerfest 2026

 Sun, 14 Jun at 12:00 pm Highland Square

Classic Crush @ The Corner Keg

 Sat, 19 Sep at 08:30 pm The Corner Keg Pub

Business After Hours

 Thu, 16 Jul at 05:00 pm The Smile Shoppe

Wicks Post St. Louis AGO National Convention Event Day Friday July 10 2026

 Fri, 10 Jul at 10:00 am Wicks Organ LLC USD 13 to 50

Highland Historical Society presents Genealogy 101

 Sat, 28 Feb at 02:00 pm Latzer Memorial Public Library USD 13 to 55

Ladies Dinner Club - Monthly

 Tue, 19 May at 06:00 pm 188 Woodcrest Drive Suite B, Highland, IL, United States, Illinois 62249

HCC Family Photo

 Sun, 12 Apr at 11:45 am 2307 Broadway, Highland, IL, United States, Illinois 62249

Riftbound: Summoner Skirmish

 Sun, 12 Apr at 12:00 pm 820 Main Street, Highland, IL, United States, Illinois 62249

MCAHCE Spring Fling Membership Luncheon

 Sat, 02 May at 11:30 am Highland Illinois Masonic Lodge 583

Investor Breakfast

 Thu, 30 Apr at 07:30 am The Olde Wicks Factory

100 Mile Club Celebration

Sun, 03 May at 10:00 am 2520 Poplar St, Highland, IL, United States, Illinois 62249

Business After Hours

 Thu, 18 Jun at 05:00 pm Steve Schmitt Ford

Raise the Roost: EvUCC Dinner Auction 2026

 Sat, 18 Apr at 05:30 pm Knights of Columbus USD 29

June Vaccine & Microchip Clinic

 Sat, 20 Jun at 08:00 am 510 W Monroe St, Highland, IL 62249, United States

HCWC Monthly Meeting - April

 Thu, 02 Apr at 06:45 pm Highland area senior center

Pop Up Party!

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

Kids Cooking Camp 2026

 Mon, 01 Jun at 08:00 am Highland Ill

EvUCC Garage Sale

 Fri, 24 Apr at 05:30 pm 2520 Poplar St, Highland, IL, United States, Illinois 62249

Spring 2026 Oil Change Project

 Sat, 30 May at 08:00 am 2307 Broadway, Highland, IL, United States, Illinois 62249

Business After Hours

 Thu, 21 May at 05:00 pm The Olde Wicks Factory

Korte Meats Rib Burn

 Sat, 02 May at 11:00 am Korte Meat Processing

THE GREENHOUSE FLORIST & GIFT SHOP with TGNY ACOUSTIC

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

Vermillion Wedding

 Sat, 02 May at 03:00 pm Schwarz Barn