Guest post by Jeremy Gill from Chicago, Illinois (Instagram: jeremys_jaunts)
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One of my favorite things about living in Chicago is how many great road trips are just a short drive away. On this getaway, I discovered Downtown Racine—a walkable lakefront destination filled with local restaurants, public art, unique experiences and small businesses that invite you to slow down and explore.
Here’s how I spent my weekend.
Day One
I checked into the DoubleTree by Hilton Racine Harbourwalk, which made the perfect home base just steps from downtown and the marina. From there, I parked the car and spent the rest of the day exploring on foot.
Since I visited on market day, my first stop was the Racine Farmers Market. Between the local vendors, fresh produce, handmade goods and live music, it was a great way to experience the community and kick off the weekend.
A short walk away, I visited the Racine Art Museum, where contemporary craft takes center stage. Then it was time to get creative at Hot Shop Glass. Watching molten glass transform into beautiful artwork was fascinating, but getting to create my own piece made the experience even more memorable.
After a full day of exploring, I headed to Olde Madrid for dinner. Their Spanish tapas are perfect for sharing, but the almond meatballs completely stole the show—they’re a must-order. It was the perfect way to slow down and enjoy the evening.
Before heading back to the hotel, I stopped at Eave, the rooftop cocktail lounge at Hotel Verdant, for drinks overlooking Downtown Racine. Great cocktails, a relaxed atmosphere and rooftop views made it the perfect nightcap.
Day Two
The next morning started with breakfast at The Maple Table, a cozy downtown favorite that definitely lived up to the hype – those homemade donut bites…yum!
Before making the drive back to Chicago, I made one final stop at the Racine Zoo. Located along the shores of Lake Michigan, it was a peaceful way to end the weekend. Having spent much of my career working in zoos, I especially appreciated visiting another organization dedicated to connecting people with wildlife in such a beautiful setting.
Jeremy’s Jaunts Picks
🍽️ Don’t miss: The almond meatballs at Olde Madrid.
🎨 Most unique experience: Creating my own glass artwork at Hot Shop Glass.
🍸 Best place to unwind: Cocktails at Eave rooftop at Hotel Verdant.
🚶 Jeremy’s tip: Wear comfortable shoes. Downtown Racine is incredibly walkable, and some of the best discoveries happen between your planned stops.
What I loved most about Downtown Racine wasn’t just one restaurant or attraction—it was how effortlessly everything came together. From art and glassblowing to rooftop cocktails, great food and the welcoming downtown atmosphere, every stop was just a short walk from the next.
If you’re looking for an easy weekend getaway from Chicago, Downtown Racine is absolutely worth adding to your list. Come with a plan, leave room to wander and let Downtown Racine surprise you.
Looking for more fun? Visit our Things to Do page for everything going on in Racine County!
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