Things To Do This Weekend May 19-21, 2023

By: Jeff Randolph 05/16/2023

When the nice weather finally breaks, the work week gets longer. These days everybody's working for the weekend. Let's look at things to do in Lake County this weekend, May 19-21, 2023.





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For a list of 25 superb Lake County satellite snaps by Google Earth click here.

It is all about chocolate in Historic Downtown Long Grove this weekend. Paddle on the Des Plaines River after launching in Libertyville. Stroll through downtown Waukegan and admire the work of local artists. There is a statewide celebration of crafter brewers. A drum corp competition takes place in Zion. Here we look at the top five things to do this weekend, May 19-21, 2023.

1. Historic Downtown Long Grove Chocolate Fest





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Anything is good if it's made of chocolate. The annual Long Grove Chocolate Festival kicks off this weekend as we celebrate the change of seasons with our sweet tooth. Be in a chocolate lover's paradise as Long Grove Confectionery Co. will be in attendance as well as many other vendors, live entertainment, and, of course, your chocolatey vices. The three-day confection party is also highlighted by a carnival Dave's World of Reptiles, a pie-eating contest, Chocolate Crafts, and more. The cocoa social features live music from bands like Eliminator, ARRA, The Gingers, American English, and more. Visit for more information.

Friday-Sunday, May 19-21; Fri.: noon-11 p.m., Sat.: 10 a.m.-11 p.m. and Sun.: 10 a.m.-6 p.m. Tickets: $5 per person, per day. Three-day tickets: $10. Historic Downtown Long Grove, various locations. 

2. Des Plaines River Canoe and Kayak Marathon along the Des Plaines River Trail





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The Des Plaines River Canoe and Kayak Marathon have been a hit for over half a century. The 18.5-mile marathon on the historic Des Plaines River begins in Libertyville at the Oak Spring Road Canoe Launch. This is the United States' second-oldest canoe race. If you are with the family, there is a brand new 5.25-mile mini-thon available starting in Potawatomi Woods in Wheeling. The Lake County Forest Preserve entity offers races for each age group to accommodate all skill levels. Be sure to look port and starboard when you cross the stream. Race registration is available at the start line or mini-thon start, payable via check or cash. Visit for more information and a map.

Sunday, May 21; First heat begins at 8 a.m., and the last heat launches at 10:38 a.m. Registration: $40 cash only. Oak Spring Road Canoe Launch, 15645 W. Oak Spring Rd., Libertyville.

3. ArtWauk in Downtown Waukegan





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The city's famed ArtWauk "paints" the town with sculptures, film, theatre, comedy, music, performance art, food, and more. The free admission Saturday art event opens the doors to all art galleries throughout Waukegan. So, fill your artistic void with the ever-extravagant monthly ArtWauk in Downtown Waukegan. In addition to the portraits, sculptures, and other creative vibes, munch on some delicious dining options downtown or feel the flow of the tunes from the live entertainment. This installment of ArtWauk also celebrates the reopening of ArtPark. The Waukegan Park District entity's grand reopening, running alongside ArtWauk, is highlighted by a ribbon cutting ceremony, live music, Jim Harrington's Art Bus, where visitors can construct arts and crafts, fun family activities, and more. Lake County Libation Trail partners Nightshade and Dark's Pandemonium Brewing, and Oppidan Spirits offer delectable brews and spirits in the downtown area of the City of Progress. Also, Green Town on the Rocks, located along the shores of Lake Michigan, is officially open for the season.

Saturday, May 20; 2-10 p.m. Downtown Waukegan, multiple locations on Genesee Street.

4. Illinois Craft Beer Week





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Illinois Craft Beer Week (ICBW) returns featuring many Lake County Libation Trail participants. During imbibe week, ICBW brew houses like Black Lung Brewing Co. in Round Lake Beach, Broken Tee Brewing Co. in Highwood, Liquid Love Brewing Co. in Buffalo Grove, Mickey Finn's Brewery in Libertyville, Phase Three Brewing and Roaring Table Brewery in Lake Zurich, Ravinia Brewing Co. in Highland Park, Tighthead Brewing Co. in Mundelein and other statewide suds stations. Brew enthusiasts are encouraged to show their support with the #DrinkIllinois Summer Passport. The initiative encourages visitors to obtain a Passport Frame from a participating brew house (or download your own at, snap a photo experiencing the Land of Lincoln beer, and post on social media utilizing #ILPassportPlus for a weekly drawing of a $50 gift card to a brewery. The summer passport program runs longer than the Prairie State, suds-influenced week (ending May 26). Visit for more information.

Friday-Sunday, May 19-26; Various locations in Lake County.

5. Drill or Die 2K23: Drill, Dance and Drumline Competition at Zion-Benton Township High School





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A post shared by Elite Striders Drill Team & Drum Corp (@elite.striders_)

For dance and drum corps fans, Zion Benton Township Highschool hosts a raucous good time with its Drill or Die 2K23. The toe-tapping event features 16 dance, color guard, and drumline groups residing in Illinois, Indiana, Iowa, Minnesota, Missouri, and Florida. The teams are judged on precision, togetherness, showmanship, presentation, uniqueness, audience reaction, and the "wow factor." Reality star Tyrus Sellers from the television show "Bring It," and social media influencer Cheerlebridee are the celebrity judges of the dance competition. Take advantage of the Friday night festivities as the participating drill and dance teams conduct a parade showcasing their talents with a $300 cash prize stepping off at 7 p.m. Friday-Saturday, May 19-20; Fri. Parade: 7 p.m., Sat. Competition: noon. Tickets: $28. Zion Benton High School, 2901 W. 21st St., Zion.

For a list of the top trendy Instagram locations in Lake County, click here.

To see more things to do this weekend May 19-21, 2023, click here.

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