The WiseGuys at Teddy O’ Brian’s Outdoor Stage!

Teddy O'Brian's Highwood 26 Sep 2025

Pantlepalooza @ The Toadstool Pub

327 Waukegan Ave, Highwood, IL 60040-1329, United States 20 Sep 2025

Pumpkin Fest Community Night & Opening Carnival

17 Highwood Ave, Highwood, IL, United States, Illinois 60040 2 Oct 2025

40th Reunion for LFHS Class of '85

28 Mile Distilling Company 20 Sep 2025

Highwood Pride presents Drag Bingo with Muffy Fishbasket!

Broken Tee Brewing Company 16 Nov 2025

Swing Night with the Flat Cats @ 28 Mile

454 Sheridan Rd 18 Sep 2025

Pumpkin Pie Eating Contest 2025

17 Highwood Ave 5 Oct 2025

Kid's Costume Contest 2025

17 Highwood Ave 5 Oct 2025

Dead Wednesday's - Deadfest Band

28 Mile Distilling Co. 8 Oct 2025

Mr. Blotto- Sunday Funday

432 Sheridan Rd, Highwood, IL, United States, Illinois 60040 28 Sep 2025

DJ ASH

28 Mile Distilling Company 19 Sep 2025

Highwood Design Week Night 2: ABLAZE Documentary Premiere Party

ABLAZE Design Group, 259 Waukegan Avenue, Highwood, IL, USA 17 Sep 2025

Reverie Stone at Toadstool Pub!

The Toadstool Pub 18 Oct 2025

Elf Invasion Pub Crawl

Highwood Ave, Highwood, IL 60040, United States 6 Dec 2025

Dose on a Sunday

432 Sheridan Rd, Highwood, IL, United States, Illinois 60040 21 Sep 2025

Beat The Beatles

432 Sheridan Rd, Highwood, IL, United States, Illinois 60040 20 Sep 2025

Mastering the Art of Networking

28 Mile Distilling Co. 16 Sep 2025

Woman Who Rock Fall 2025

28 Mile Distilling Company 16 Sep 2025

Dead Wednesday's - Deadfest Band

28 Mile Distilling Co. 12 Nov 2025

Dead Wednesday with The County Line Jam Band

28 Mile Distilling Co. 24 Sep 2025