Old Town was once an enclave for artists and queer Chicagoans. What better way to celebrate that history during Pride month than at the Old Town Art Fair and the Wells Street Art Fest this weekend? Today, I’m sharing spots to hang out in my old stomping grounds of Old Town, where I went to school and hung out with friends.
Something to Eat
Many people come to Twin Anchors to feast on ribs at the same spot where Frank Sinatra was a regular decades ago. Want something sweet? The Fudge Pot has been selling chocolates since the ‘60s.
Something to Drink
Spend a Summertime Chi afternoon playing games at Utopian Tailgate. If you’re looking for a speakeasy vibe, visit Marge’s Still, the longest-running tavern in the city.
Something to See
There’s no shortage of entertainment options in Old Town from plays at A Red Orchid Theatre to comedy shows at Zanies. But it’s The Second City that attracts locals and tourists alike to see up-and-coming talent. Want to join the ranks of Second City alumni like Steve Carell and Stephen Colbert? You can take improv and writing classes at the famous comedy club, too.
Something to Do
Old Town is home to beautiful mansions like the Henry Gerber House, a national landmark commemorating the Chicagoan who founded the country’s first gay rights group in the 1920s. Keep the learning going at one of my favorite field trips growing up: the Chicago History Museum. The next free days for Illinois residents are June 19, 23, 26, and 29.
Boundaries of Old Town. (Google Maps)
