Put on your most comfortable shoes, because you’re about to do some festival hopping in Chicago this week. It all starts with the mole sauce festival (yes, it’s as delicious as it sounds), followed by a music festival in Lakeview. Of course, Chicago goes all out for the Memorial Day Parade, but try not to run out of energy before Bike the Drive.
AFAR Local is our weekly insider guide to the best of what's happening in cities around the U.S.
May 27–29 | Festival
Mole De Mayo
In the heart of Chicago’s Pilsen neighborhood, you’ll find the best Mexican restaurants in the city any day of the week. This week, you’ll also find the highly anticipated mole festival, where local chefs will fight to see whose version of the Mexican sauce rules. The open-air fest and market won’t skimp on entertainment, including music, a wrestling ring, and plenty of other food, drinks, and local businesses.
Times vary | 18th St. at Ashland Ave., Chicago | Free | website
May 28 | Parade
Chicago Memorial Day Parade
The Memorial Day Parade has been a Chicago tradition since 1870. It’s big and fantastic, with uniformed officers, impressive floats, and treats for the kids, making it one of the most fun Chicago events of the year. It’s also one of the most important, with people from all backgrounds showing up to enjoy the day and honor the soldiers who gave their lives to defend our country.
12 p.m. | State St. from Lake St. to Van Buren, Chicago | Free | website
May 28–29 | Festival
Belmont-Sheffield Music Festival
This two-day outdoor block party feels like the best local neighborhood party you never had. Belmont-Sheffield gathers the best cover bands, which then cover the biggest rock hits from the ‘80s, ‘90s, and beyond on the days of the event. Add booze and street food into the mix, and you’ve got yourself the makings of a perfect Chicago weekend.
12–10 p.m. | North Sheffield from Belmont to Roscoe, Chicago | $5 | website
Courtesy of Belmont-Sheffield Music Festival
Grand Rapids, Michigan
About 30 breweries reside in the Grand Rapids area, just three hours out of Chicago, making the Michigan city a top pick for craft beer snobs. Founders Brewing Company and HopCat are two must-try stops. Add some culture to the mix by checking out the 125-acre Frederik Meijer Gardens and Sculpture Park and the Grand Rapids Public Museum before jotting over to Grove for a fancy dinner.
May 29 | Bike ride fundraiser
Bike the Drive
This is the day that cyclists anticipate and drivers dread. The entirety of Lake Shore Drive (yes, that gorgeous highway by the lake) will be closed for five hours, leaving it open solely for cyclists to enjoy. The non-competitive fundraiser, which benefits the Active Transportation Alliance to improve biking, walking and transit, is a classic Chicago event open to everyone. The whole route is 30 miles, but you’re welcome to stop at any point along it (we suggest a mid-ride breakfast or brunch).
5:30 a.m. | Multiple starting locations | From $53 | website
Danielle Braff lives in Chicago with her husband, two daughters, two cats, and her dog. When she’s not writing, she’s out photographing her city and running around frantically trying to fit as many events as she can into her day. You can check out her other articles at Daniellebraff.com.
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