Top Annual Highland Park IL Events & Festivals

Highland Park IL Events & Festivals

From music to the arts, you’ll find plenty of events and festivals to choose from throughout the year in Highland Park. Here are some of the best on the calendar this year:

Bitter Jester Music Festival

The Bitter Jester Music Festival celebrates its 16th season this summer. The fun begins in late May with an opening night concert and continues through June with several more concerts. A Grand Finale Concert and fireworks are planned for the 4th of July. The professional music competition brings in up-and-coming musicians, including solo acts and bands from across the Midwest. 

Port Clinton Art Festival

The Port Clinton Art Festival takes place at the end of August in Downtown Highland Park. The weekend brings in hundreds of artists with photos, furniture, sculptures, jewelry, and paintings for sale. The annual event has been a tradition for decades, with artwork, food, and drinks for sale, too. Downtown streets close so visitors and locals can stroll through the festival booths. 

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Ravinia Farmers Market

For locally grown and sourced products, make plans to attend the Ravinia Farmers Market in Jens Jensen Park. In operation since the late 1970s, the farmers market operates on Wednesdays from early June through late October. 

Food Truck Thursdays

The Ravinia District is the place to check out an eclectic mix of food and drinks on Thursday nights from early July through early September. Food Truck Thursdays has a changing lineup of food trucks each week, so be sure to check back on a weekly basis for new selections. 

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