May
M19
T20
W21
- Dead Wednesday at 28 Mile featuring Grateful Dead tribute Trouble Ahead
T22
F23
- VBB at the Toadstool Pub in Highwood
- Tom’s Garage at Teddy O’Brians in Highwood
S24
- Grateful Jazz Band
- Deadfest Band Jammin' at Teddy O'Brians!
S25
- Davidson County Band Summer Party
- Black Diamond Sessions Live At Toadstool Pub/Feat. Johnny Martinez and Gracie Lubisky
M26
T27
W28
- Dead Wednesday featuring Grateful Dead tribute The County Line Jam Band
T29
F30
- THE FUNK OUT
S31
- Queen Explosion
Jun
S1
M2
T3
W4
- Dead Wednesdays Featuring Black Throated Wind @ 28 Mile
- CELEBRATE HIGHWOOD'S 2025 SERIES OF FAMILY-FRIENDLY FESTIVALS AND EVENTS
- Highwood's Weekly Evening Gourmet Market
T5
F6
- Northwest Corner
- Northwest Corner-First Friday Upgrade-June 2025
- Highwood Pride Presents Pridefest 2025: Fierce & Fabulous
S7
- Terrapin Flyer at Teddy’s
- FunkTonic at Toad Stool Pub!
S8
- The Chicago Red Line
M9
T10
W11
- Dead Wednesday with Deadfest Band at 28 Mile Distilling Co.
T12
F13
- Rollover at Toadstool in Highwood
S14
- Davidson County Band- Paytonpalooza 6/14/2025!
S15
M16
T17
- Low-reen & Harpdog and Friends host the 3rd Tuesday Blues Jam @ Wooden Nickel!
W18
T19

Events in Highwood

Park 540

Fri, 11 Jul

Selling fast

Canlan Sports

Fri, 27 Jun

Featured

Yellow Box

Fri, 22 Aug

Highwood's Most-Loved

All Categories

Bloody Mary Fest

111 North Ave, Highwood, IL 60040-1521, United States

Sun, 17 Aug
Davidson County Band Summer Party

Nite N' Gale Restaurant

Sun, 25 May
Terrapin Flyer at Teddy’s

Teddy O'Brian's

Sat, 07 Jun
Grateful Jazz Band

454 Sheridan Rd

Sat, 24 May
INFERNO FEST 2025

Everts Park

Wed, 25 Jun
FunkTonic at Toad Stool Pub!

The Toadstool Pub

Sat, 07 Jun