Events and Things to Do in Highland Park, IL

Thursday, June 11

Featured

Chris RWK 'I Left My Heart in Illinois' Solo Exhibition

JUN

11

6:00 PM

524 Sheridan Rd, Highwood, IL

Public art continues to shape the cultural landscape of Highwood with the unveiling of “For giving”, a new sculpture by...

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Friday, June 12

Saturday, June 13

Featured

Public Tour of the Historic Ragdale Campus

JUN

13

10:00 AM

1230 N Green Bay Rd, Lake Forest, IL

Ragdale, the nationally acclaimed artists’ residency program, located on the former Arts and Crafts country estate of architect...

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Thursday, June 18

Featured

Highland Park Wine Stroll

JUN

18

5:00 PM

Highland Park, IL

Sip, Shop & Stroll Through Downtown Highland Park The Highland Park Wine Stroll returns Thursday, June 18 for an evening of...

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Saturday, June 20

Featured

Kick-off weekend for Ragdale Ring Summer Performance Series

JUN

20

6:00 PM

1230 N Green Bay Rd, Lake Forest, IL

The 2026 Ragdale Ring Summer Performance Series kicks off on June 20 with a world premiere dance performance of Circle of...

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Sunday, June 21

Featured

Ragdale Family Day at Ragdale Ring Summer Performance Series

JUN

21

1:30 PM

1230 N Green Bay Rd, Lake Forest, IL

Enjoy a special time out at Ragdale's Family Day! Fun for everyone, the day's program includes performances of the comedy show...

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Sunday, June 7

• KZ Sings: 30 Years and Growing 4:00 pm

  Nichols Concert Hall, 1490 Chicago Avenue, Evanston

  
  
• Kol Zimrah Sings: 30 Years and Growing 4:00 pm

  Nichols Concert Hall, 1490 Chicago Ave, Evanston

  
  

Tuesday, June 9

• Breakfast before Business with Anna Marcolin 7:30 am

  Highwood City Hall, 17 Highwood Ave, Highwood, IL, 60040

  
  

Wednesday, June 10

• Ribbon Cutting and Public Sculpture Dedication 5:30 pm

  341 Waukegan Ave, Highwood

  
  

Thursday, June 11

• Chris RWK 'I Left My Heart in Illinois' Solo Exhibition 6:00 pm

  524 Sheridan Rd, Highwood

  
  
• Speakeasy Comedy Show - Stand-Up Comedy @ Yana's Speakesy HP 8:00 pm

  Yana's Speakeasy, 465 Roger Williams Ave, Highland Park

  
  

Friday, June 12

• Cartier Eyewear Trunk Show @ Eye Magic By Michael Scott 5:00 pm

  605 Elm Pl, Highland Park

  
  

Saturday, June 13

• Public Tour of the Historic Ragdale Campus 10:00 am

  1230 N Green Bay Rd, Lake Forest

  
  
• Arts on Sheridan 10:00 am

  484 Central Ave, Highland Park, IL 60035

  
  

Sunday, June 14

• Arts on Sheridan 10:00 am

  484 Central Ave, Highland Park, IL 60035

  
  

Wednesday, June 17

• Northbrook Farmers Market Opening Day Bash – 2026 Season Kickoff 7:00 am

  Meadow Shopping Plaza Shopping Center, Cherry Ln, Northbrook

  
  

Thursday, June 18

• Highland Park Wine Stroll 5:00 pm

  Downtown Highland Park, Highland Park

  
  
• Spill Sessions: Behind the Murals 6:00 pm

  440 Green Bay Rd, Highwood

  
  

Friday, June 19

• Highland Park Announces 2026 EnjoyHP Lineup 5:00 pm

  Highland Park

  
  
• Taste of Highland Park Returns June 19–20! 5:00 pm

  Central Avenue, between Second St. and St. Johns Ave., and in Port Clinton Square (600 Central Ave.

  
  

Saturday, June 20

• Kick-off weekend for Ragdale Ring Summer Performance Series 6:00 pm

  1230 N Green Bay Rd, Lake Forest

  
  

Sunday, June 21

• Ragdale Family Day at Ragdale Ring Summer Performance Series 1:30 pm

  1230 N Green Bay Rd, Lake Forest

  
  

Wednesday, June 24

• Inferno Fest 4:30 pm

  111 North Ave, Highwood

  
  

Thursday, June 25

• The Memory Keepers: An Evening with Holocaust Memoir Authors 7:00 pm

  Congregation B'nai Tikvah, 1558 Wilmot Rd, Deerfield

  
  

Friday, June 26

• Live Stand-Up Comedy @ Madame Zuzu's 7:30 pm

  Madame Zuzu’s, 1876 1st St, Highland Park