inspiration

A Surprise Garden Walk!

A random sign led us to Chicago’s Dearborn Garden Walk—and suddenly we were exploring 20 dreamy private gardens!

Charlie Yellow

• 3 min read
A Surprise Garden Walk!
With pink and purple balloons all over the street, who wouldn’t get curious and want to peek inside!?

Today, I had an errand in downtown Chicago, and I kept seeing pink and purple balloons and signs saying “This way, please” I got curious, so my husband and I followed the signs… and somehow ended up in the courtyard of a condo!

There was a madam standing at the entrance, so I gave her a cheerful “Hello!” and walked right in. A few people were quietly enjoying the garden. But then… I noticed everyone had wristbands! I panicked—“Wait, did we just crash some private event!?”

But a kind volunteer lady came over and gently explained, “Today’s the Garden Walk. Come back after you grab tickets at the check-in table,” and she even handed us a map. So sweet!

And just like that, we joined the 65th Dearborn Garden Walk, hosted by the North Dearborn Association!

Boho Bouquet Bar (@bohobouquetbar) gave us fun tips on how to put together a bouquet—how to mix colors, rescue a droopy gerbera, and arrange flowers like a pro. Lots of gasping, laughing, and learning!

This ivy-covered garden was so peaceful, you’d never guess we were in downtown Chicago. It was the perfect hideaway for Yogi the cat.

In one garden, the owner noticed that black swallowtails loved laying eggs on her dill and parsley. Instead of treating the caterpillars like pests, she just let them grow—and had fun watching them every day. I loved her open-hearted way of enjoying nature!
This is one of Chicago’s two remaining Wooden Alleys! The original was laid in 1909, but this version was redone in 2011. It became part of the National Register of Historic Places in 2002. Looks cool but must be tricky to maintain!

This garden was pure hard work and passion! The owner said she spends up to 9 hours a day gardening—and her husband has to remind her to drink water or eat. Totally relatable though. Time must fly in a garden this beautiful!

One of the ~20 spots was actually an apartment where Hemingway lived back in the day!

We visited about 20 different spots in 2 hours, and getting to peek into so many beautifully cared-for private gardens felt like such a luxury. What a lucky, leafy afternoon!