Events and Things to Do in Highland Park, IL

Thursday, May 21

Featured

Debate without Hate

MAY

21

6:00 PM

Trinity Episcopal Church, 425 Laurel Ave, Highland Park, IL

A civil debate between national political figures. Sponsored by The Highland Park Art Center. Free admission.

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Friday, May 22

Featured

We Do Estate Sales vintage treasures and more Deerfield Moving Sale

MAY

22

10:00 AM

990 Heather Rd, Deerfield, IL

Come shop with us May 22-23, Friday and Saturday 10-2. We’ve got tons of vintage treasures , fabulous selection of vintage and...

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Saturday, May 23

Featured

Wake up to donuts on your doorstep from Do-Rite! Order by 10pm Friday.

MAY

23

7:00 AM

Highland Park, IL

Do-Rite Donuts is coming to you on Saturday, May 23rd! Enjoy a wide variety of freshly baked artisanal donuts in unusual...

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Sunday, May 24

Featured

Celebrate Memorial Day with BBQ, Steaks, Seafood, Pizza, Italian & Sweet Treats Delivered!

MAY

24

10:00 AM

Evanston, IL

Stay in and enjoy standout meals from the city’s best local restaurants. DwellSocial brings your favorites straight to your...

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Thursday, May 21

• Debate without Hate 6:00 pm

  Trinity Episcopal Church, 425 Laurel Ave, Highland Park

  
  

Friday, May 22

• We Do Estate Sales vintage treasures and more Deerfield Moving Sale 10:00 am

  990 Heather Rd, Deerfield

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

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

  
  

Saturday, May 23

• Wake up to donuts on your doorstep from Do-Rite! Order by 10pm Friday. 7:00 am
  
  

Sunday, May 24

• Celebrate Memorial Day with BBQ, Steaks, Seafood, Pizza, Italian & Sweet Treats Delivered! 10:00 am
  
  

Wednesday, May 27

• Crystal Bowl Sound Meditation 6:30 pm

  The Art Center Highland Park, 1957 Sheridan Rd, Highland Park

  
  

Sunday, May 31

• Brahms' Celebration 3:00 pm

  Highland Park Community House, 1991 Sheridan Rd, Highland Park

  
  

Wednesday, June 3

• Celebrate Highwood Announces 2026 Series of Family-Friendly Festivals and Events 4:30 pm

  111 North Ave

  
  

Saturday, June 6

• Fox Valley at the Fairgrounds Antiques Show 9:00 am

  DuPage Event Center & Fairgrounds, 2015 Manchester Rd, Wheaton

  
  

Sunday, June 7

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

  Nichols Concert Hall, 1490 Chicago Ave, Evanston

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

  Nichols Concert Hall, 1490 Chicago Avenue, Evanston

  
  

Thursday, June 11

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

  Yana's Speakeasy, 465 Roger Williams Ave, 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

  
  

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.

  
  

Thursday, June 25

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

  Congregation B'nai Tikvah, 1558 Wilmot Rd, Deerfield