Walk a Mile on 87th Street and Stony Island Avenue

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

1. We pick an area within city limits.
2. We pick a mile to walk (east on 87th Street then south on Stony Island Avenue).
3. We recommend ~10 things to do in that mile.

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.

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.