Upcoming Highwood Events

Check out what's happening all around Highwood, IL

Great Highwood Pumpkin Festival

 Fri, 02 Oct at 12:00 pm 111 North Ave, Highwood, IL 60040-1521, United States

🧄 Garlic Fest 2026 with music by A Tribute to Old Blue Eyes, sponsored by Scotty's on Sheridan

 Wed, 12 Aug at 04:30 pm 111 North Ave, Highwood, IL 60040-1521, United States

🍅 Bloody Mary Fest

 Sun, 16 Aug at 10:00 am 111 North Ave, Highwood, IL 60040-1521, United States

Highwood Days Carnival & Taste of Highwood🎡

Fri, 17 Jul at 05:00 pm 111 North Ave, Highwood, IL 60040-1521, United States

Highwood Evening Gourmet Market with music by Stevie Craig Band, sponsored by Bella Via

 Wed, 03 Jun at 04:30 pm 111 Highwood Ave, Highwood, IL, United States, Illinois 60040

Highwood Evening Gourmet Market with music by Rollover

 Wed, 08 Jul at 04:30 pm 111 Highwood Ave, Highwood, IL, United States, Illinois 60040

Kick-Off to Summer Carnival 🎪

 Fri, 05 Jun at 05:00 pm 406 Sheridan Rd, Highwood, IL 60040-1309, United States

Highwood Evening Gourmet Market with music by Telstar, sponsored by The Music Gallery

 Wed, 26 Aug at 04:30 pm 111 Highwood Ave, Highwood, IL, United States, Illinois 60040

🍹Highwood’s Margarita Night with music by South of Disorder, sponsored by the Budnik Family!

Wed, 29 Jul at 04:30 pm 111 North Ave, Highwood, IL 60040-1521, United States

Highwood Evening Gourmet Market

 Wed, 10 Jun at 04:30 pm 111 North Ave, Highwood, IL 60040-1521, United States

Inferno Fest with music by Los Perros Cubanos🌶️

 Wed, 24 Jun at 04:30 pm 111 North Ave, Highwood, IL 60040-1521, United States

Diamondback returns to The Toadstool Pub!

 Fri, 24 Apr at 07:30 pm The Toadstool Pub

‘COME BACK INTO FOCUS’ HONORING THE CHAIRWOMEN OF THE PAST 60 YEARS

 Thu, 30 Apr at 06:00 pm 28 Mile Distilling Company

Low-reen & Harpdog and Friends host the 3rd Tuesday Blues Jam @ Wooden Nickel!

 Tue, 19 May at 07:00 pm Legendary Wooden Nickel

BEAUTY AND THE BEETCH

 Sun, 19 Apr at 03:00 pm 28 Mile Distilling Company USD 45 to 66

The Funk Out @Toadstool Pub

 Sat, 18 Apr at 08:00 pm The Toadstool Pub

SIL IN-PERSON Networking

 Wed, 15 Apr at 04:30 pm 28 Mile Distilling Company USD 13

Rollover at Toadstool Pub 🎶

 Fri, 19 Jun at 07:30 pm The Toadstool Pub

Windy City Rev Ups - Live at The Toadstool Pub

 Fri, 29 May at 08:00 pm The Toadstool Pub

Deadfest Band at 28 Mile Distilling

Wed, 10 Jun at 07:00 pm 28 Mile Distilling Co.

FunkTonic at Toadstool Pub!

 Sat, 09 May at 08:00 pm The Toadstool Pub

Wildwood Country @ Toadstool Pub in Highwood

 Sun, 28 Jun at 12:00 pm The Toadstool Pub