This is a very personal walk because my great-grandparents lived in Calumet Heights my entire life. Some of the places on this route have been around for as long as I can remember, and some are fairly new.
How it Works
- We pick an area within city limits.
- We pick a mile to walk (east on 87th Street then south on Stony Island Avenue).
- We recommend ~10 things to do in that mile.
A few stops along 87th Street and Stony Island Avenue
How to Get There
- No. 28 bus to Stony Island and 87th Street
- Metra Electric to 87th Street (Woodruff)
- Divvy at South Dauphin and 87th Street
What to Do
I stop for a quick walk through Lorraine Dixon Park before taking my 16-year-old skates to The Rink. Many would call it the home of Chicago JB skating — the JB for James Brown, of course.
After leaving The Rink, you can stop for a quick cocktail at Darrin’s or grab a plate of chicken tips at Smoke's Bistro.
I’ve got more of a sweet tooth so I head to Justice of the Pies, making sure to stop and take a pic of the mural of Farley “Jackmaster” Funk. Completed in 2022 by artist Rahmaan Statik, it is not the last Statik we’ll see on this walk.
When I get to the bakery, I can’t help but admire how beautiful the building is. The brick, black accents, and large windows help it stand out in the neighborhood. With so many choices to pick from, I grab a banana pudding, lemon lavender cookie, and a slice of caramel peach pie.
Stop at Lorraine Dixon Park, Wingz It Iz, a mural of Farley “Jackmaster” Funk, Justice of the Pies, and The Rink all in a mile. (Jacoby Cochran / City Cast Chicago)
On Sundays, you have a choice of where to watch the Bears game: with a daiquiri flight at S2 City Grill or with a beer and cigar at Family Den. My great-grandfather loved going to the Family Den every week for decades.
Three of my favorite murals are nearby: “Light The Spark” is by 88th and Stony, and “Space Odyssey” and “Stony Island Soul” are by 90th and Stony.
Before heading to my mom’s, I stop by Wingz It Iz for a six-piece of their famous garlic wings.
