Classic’s Community Calendar of Events in Lake County for May 2025 (Waukegan, IL)

May 1, 2025

Spring is in full swing and we’re gearing up for warm weather fun in the sun! Enjoy a plethora of family friendly activities and date-night ideas as well as plenty of “back to nature” fun. We’re sharing all that and more on this month’s edition of Classic’s Community Calendar of Events in Lake County Illinois for May 2025.

First Fridays are back on Mainstreet in Libertyville. Head downtown on May 2nd from 10AM to 9PM for a chance to dine, shop, and support your local community! Downtown shopowners and restaurants are offering special discounts for the occasion and parking is free.

Residents 21+ can enjoy a “Dos De Mayo” party at the Patty Turner Center in Deerfield on Friday May 2nd from 6:30PM to 8PM. Tickets are $35-$45 per person including appetizers, drinks, live music, salsa line dance, and more.

The thrilling Chicagoland Monster Truck Wars are barreling into town on Saturday May 3rd at 12PM and 6PM at the Lake County Fairgrounds and Event Center in Grayslake.

The 13th Annual GLMV Extreme Block Party and Family Expo is happening on Saturday May rd from 10AM to 3PM at the DoubleTree Mundelein in Mundelein.

Art in the Garden at Fox Lake’s Community Garden is taking place at Lakefront Park in Fox Lake on Saturday May 3rd from 12PM to 2PM.

Grayslake Art Alliance’s Mayfest is taking place at the Grayslake Heritage Center and Museum from 12PM to 4PM on Saturday May 3rd.

The Spring Into Nature Family Festival at the Heller Nature Center is happening on May 10th in Highland Park. Prices are $24-$28 and include music on the lawn, a picnic, giant bubble making, and a walk in the woods among other family friendly fun. Preregistration is preferred for this entirely outdoor event.

Stop by the Marketplace Cafe on the May 17th Artwauk event for a special Charcuterie menu from 5Pm to 9PM on May 17th in Waukegen on Genesee Street.

Long Grove Chocolate Fest will be taking over Historic Downtown Long Grove on May 16th, 17th, and 18th! There will be live music, plenty of hands on activities for kids, food vendors, and of course plenty of chocolate!

Lake County Food Truck Festival is rolling into the Lake County Fairgrounds and Event Center in Grayslake on Friday May 23rd from 12PM to 9PM. Local and regional businesses will be sampling their wares and an immense array of cuisines to explore and try!

Waterfront Market at Waukegan Harbor Marina starts its season on May 23rd and then returns on June 27th, July 25th, August 22nd, and September 26th from 5PM to 8PM at Siver Park. Shop locally made products and handmade goods, sample delicious food and drinks, and enjoy live music at Green Town on the Rocks.

Waukegan’s Memorial Day Parade and Ceremony will be kicking off on Monday May 26th at N. Martin Luther King Jr Avenue followed by a commemoration at Veterans Plaza. The parade begins promptly at 10:45AM so make sure you’re ready to go for best viewing!

The Chicagoland Antique, Advertising, Slot Machine, and Juke Box Show will be coming to town on Friday May 30th and Saturday May 31st at the LAke County Fairgrounds and Event Center in Grayslake.