Upcoming Highland Events

Check out what's happening all around Highland, IL

2025 Fall Artisan Market

Sat, 22 Nov at 10:00 am Highland High School

Highland Chamber of Commerce Lighted Christmas Parade

Fri, 28 Nov at 06:30 pm Highland Square

Christmas Concert: Sing out! Ring out!

Sat, 13 Dec at 07:00 pm St. Paul Catholic Church Highland

Every Little Thing Band Performing at Corner Keg!!

Sat, 06 Dec at 09:00 pm The Corner Keg Pub

Cookie Crumb Trail

Sat, 06 Dec at 10:00 am Highland Square

Tom O DJ at Old Time Pub

Fri, 14 Nov at 08:00 pm Old Time Pub

Digimon: Evolution Cup

Fri, 12 Dec at 06:30 pm 820 Main Street, Highland, IL, United States, Illinois 62249

Pop-Up Cookie Stand

Sat, 22 Nov at 10:00 am Twice the Ice Highland, IL (Highland, IL)

Night of Thx!

Wed, 19 Nov at 06:00 pm 1317 Pestalozzi St, Highland, IL, United States, Illinois 62249

Boot Camp Pop Up

Sat, 15 Nov at 08:30 am Korte Rec Center

New sermon series! Of God and Money

Sun, 16 Nov at 10:00 am 820 Mulberry, Highland, IL

Black Friday Popup Sale

Fri, 28 Nov at 04:00 pm 1007 Washington Street OPEN Wednesday through Friday 11-5 Saturdays 10-2, Highland, IL

Pop-Up Cookie Stand!

Sat, 15 Nov at 10:00 am Twice the Ice Highland, IL (Highland, IL)

Sunday 10:30 Study "All Things New"

Sun, 23 Nov at 10:30 am 2307 Broadway, Highland, IL, United States, Illinois 62249

Holiday Sip & Shop 2025🎄🎁

Sun, 23 Nov at 11:00 am The Olde Wicks Factory

Thanksgiving for the Community

Sat, 22 Nov at 05:00 pm Highland Illinois Masonic Lodge 583

Free Photo with Santa

Sat, 13 Dec at 10:00 am 1007 Washington Street OPEN Wednesday through Friday 11-5 Saturdays 10-2, Highland, IL

Pokemon Trade Night!

Sat, 15 Nov at 05:00 pm 820 Main Street, Highland, IL, United States, Illinois 62249

Small Business Saturday 15% off Storewide Sale

Sat, 29 Nov at 10:00 am 1007 Washington Street OPEN Wednesday through Friday 11-5 Saturdays 10-2, Highland, IL

Small Business Saturday - Caught in the Act

Sat, 29 Nov at 09:00 am 1216 Main St, Highland, IL, United States, Illinois 62249

Mouse Races - Roughnecks and Lady Roughnecks

Sat, 03 Jan at 07:00 pm KC Hall Highland Il

Chamber Holiday Happy Hour

Fri, 12 Dec at 05:00 pm Lindendale Park Ballroom

Olde Wicks Factory Wedding Show | Bride Registration (1/11/26)

Sun, 11 Jan at 11:00 am The Olde Wicks Factory Free

Highland - Line Dance Lessons 7-9PM

Wed, 19 Nov at 07:00 pm 1900 VFW Rd, Highland, IL 62249-2343, United States

A Wicked Weekend on the Highland Square

Thu, 20 Nov at 04:00 pm 914 Main Street, Highland, IL, United States, Illinois 62249

Resident & Family Thanksgiving Meal! 🦃

Thu, 20 Nov at 12:00 pm 1450 26th St. , Highland, IL, United States, Illinois 62249

Hunter Sharp Live - Christmas Parade After Party at Old Time Pub

Fri, 28 Nov at 09:00 pm 12258 Highland Road, Highland, IL, United States, Illinois 62249

Highland Holiday Home Tour

Sat, 06 Dec at 04:00 pm Cedarhurst Senior Living of Highland USD 29 to 34

Gingerbread House Decorating

Sat, 06 Dec at 09:30 am 801 Washington St, Highland, IL

Santa Paws

Sun, 07 Dec at 10:00 am 803 3rd St, Highland, IL, United States, Illinois 62249

ShortMist @ The Corner Keg

Sat, 13 Dec at 08:30 pm The Corner Keg Pub

AlphAs Christmas Party - For the Ladies!

Fri, 05 Dec at 06:30 pm Highland Knights of Columbus Council 1580

MTG: Avatar the Last Airbender Prerelease

Sat, 15 Nov at 12:00 pm 820 Main Street, Highland, IL, United States, Illinois 62249

MTG: Lorwyn Eclipsed Prerelease

Sat, 17 Jan at 12:00 pm 820 Main Street, Highland, IL, United States, Illinois 62249

Raising Kids in a Digital World

Sat, 22 Nov at 10:00 am 1001 9th St, Highland, IL, United States, Illinois 62249

Illinois Family Reading Night

Thu, 20 Nov at 06:00 pm 1001 9th St, Highland, IL, United States, Illinois 62249

MTG: Lorwyn Eclipsed Store Champ

Sat, 17 Jan at 12:00 pm 820 Main Street, Highland, IL, United States, Illinois 62249

Fish Fry Friday

Fri, 14 Nov at 04:00 pm 1900 VFW Rd, Highland, IL, United States, Illinois 62249

Last Pop Up Party of 2025!

Fri, 21 Nov at 10:00 am 810 and 808 Broadway, Highland, IL

Holthaus Classic 2026

Sat, 31 Jan at 02:00 pm 212 Walnut street HiTop Bowl, Highland, IL

Christmas Concert: Sing out! Ring out!

Sun, 14 Dec at 03:00 pm St. Paul Catholic Church Highland

Preschool Story Time

Mon, 17 Nov at 10:00 am 1001 9th St, Highland, IL, United States, Illinois 62249

Santa's Workshop - A FREE Christmas Experience For Kids

Sat, 06 Dec at 09:00 am Highland Illinois Masonic Lodge 583

2025 Highland Muny Band Christmas Concert

Sun, 21 Dec at 03:00 pm Weinheimer Center

Wild Ride Wednesday @ Old Time Pub

Wed, 26 Nov at 06:00 pm 12258 Highland Road, Highland, IL, United States, Illinois 62249

🎅✨ Santa’s Senior Social!

Wed, 17 Dec at 11:00 am 1450 26th St. , Highland, IL, United States, Illinois 62249

UVS: Guilty Gear Strive Prerelease

Sun, 23 Nov at 04:00 pm 820 Main Street, Highland, IL, United States, Illinois 62249

Madison County Fair Chicken Fundraiser Dance

Sat, 07 Feb at 06:30 pm 2025 Park Hill Dr, Highland, IL, United States, Illinois 62249

HIGHLAND DANCE Night - Sat, Nov 22nd - THEME: Goin' Country

Sat, 22 Nov at 07:00 pm 1900 VFW Rd, Highland, IL 62249-2343, United States

Book Club

Thu, 22 Jan at 06:30 pm 1001 9th St, Highland, IL, United States, Illinois 62249

Raise the Roost: EvUCC Dinner Auction 2026

Sat, 18 Apr at 05:00 pm Knights of Columbus

Me N D at Holiday Sip n Shop

Sun, 23 Nov at 12:00 pm The Olde Wicks Factory

Business After Hours

Thu, 15 Jan at 05:00 pm Knights of Columbus

Next Stop Comedy at Schlafly Highland Square! - Highland, IL

Sat, 18 Oct at 08:00 pm Schlafly Highland Square USD 28

ShortMist @ Old Time Pub

Sun, 14 Dec at 03:00 pm Old Time Pub

2025 Gobble Hobble

Thu, 27 Nov at 07:00 am Korte Rec Center

Fry Project returns to Corner Keg in Highland IL! 🎶🍻🎶

Sat, 15 Nov at 08:30 pm The Corner Keg Pub

Day Retreat: Thriving (Not Just Surviving) Through the Holidays

Sat, 06 Dec at 09:00 am Mosaic Church - Highland

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