Five Unexpected Places to Stop on a Drive from Chicago, IL to Kenosha, WI

If you're planning a road trip from Chicago, IL to Kenosha, WI, there's a lot to explore along the way. The drive takes a little under two hours, but there are plenty of opportunities to discover charming small towns, beautiful natural landscapes, and unique attractions that make for the perfect pit stop. Here are five unexpected places to consider visiting on your next Midwest road trip.

Halfway Point: Vernon Hills, IL

Before diving into the list, it's worth mentioning Vernon Hills, the halfway point between Chicago and Kenosha. Vernon Hills is an upscale suburb that's perfect for a quick lunch break or a little bit of shopping. For food, check out Wildfire, a classic steakhouse that's been a local favorite for over 20 years. For shopping, stop by the Hawthorn Mall, where you'll find over 100 stores, including popular retailers like Macy's, Forever 21, and H&M.

1. Wilmot Mountain, WI

About 40 minutes north of Vernon Hills, you’ll find Wilmot Mountain, a ski resort that’s been a go-to destination for winter sports enthusiasts since 1938. While the ski season is obviously its biggest draw, Wilmot Mountain is still worth a visit during the summer months. The resort offers various outdoor activities, including mountain biking, scenic chairlift rides, and a ropes course. Plus, if you’re feeling adventurous, you can try out their year-round indoor skydiving facility.

For food, don’t miss Beulah’s Restaurant, located inside the resort’s lodge. They serve up classic comfort food in a cozy, lodge-like setting. Their menu features “Northwoods” staples like cheese curds, deep-fried fish, and burgers.

2. Robert R. McCormick Foundation Bridge, IL

As you continue north, you’ll cross over the Robert R. McCormick Foundation Bridge, a unique structure that spans the Des Plaines River. The bridge was built in 1937, but it’s gone through extensive renovations in recent years to make it more pedestrian-friendly.

While the bridge itself is a marvel to behold, the real hidden gem is the natural area that surrounds it. The Des Plaines River Trail is a popular spot for hiking, biking, and birdwatching. Stop at the nearby McDonald Woods Forest Preserve for a peaceful picnic or a glimpse of local wildlife.

3. Bristol Renaissance Faire, WI

Just a few miles north of the Wisconsin border, you’ll find the Bristol Renaissance Faire, a yearly event that runs from early July to Labor Day. If you’re a fan of all things medieval, this is the perfect place to visit. You’ll see jousting tournaments, theatrical performances, and artisan demonstrations. The sixteenth-century-style village is also full of unique vendors selling handmade crafts and delicious food.

Speaking of food, the food vendors at the Bristol Renaissance Faire are a highlight. Don’t miss the giant turkey legs, which have become a bit of a legend among fair-goers.

4. North Beach, WI

Located in downtown Racine, North Beach is a hidden gem that’s worth a detour. The beach is one of the best in the Midwest, and it’s considered a “Blue Wave” beach, meaning it meets certain environmental and safety criteria.

If you’re not in the mood for swimming, North Beach still has plenty to offer. Take a stroll on the boardwalk, which offers stunning views of Lake Michigan. Check out the nearby Racine Art Museum to admire their collection of contemporary crafts.

For food, grab a bite at Reefpoint Brew House, located right on the beach. They serve up pub food with a focus on locally-sourced ingredients, so you can feel good about what you’re eating.

5. Mars Cheese Castle, WI

No road trip in Wisconsin is complete without a stop at a cheese shop, and Mars Cheese Castle is one of the best. This family-owned shop has been a Kenosha landmark since 1947, and it’s filled to the brim with local cheeses, meats, and other goodies.

Aside from the shop itself, Mars Cheese Castle is an attraction in its own right. Take some time to appreciate the whimsical castle-inspired facade, complete with turrets and a drawbridge. The shop also has a cafe that serves up delicious sandwiches, cheese plates, and wine.

Why You Should Take This Trip

It’s easy to get stuck in a routine and forget to explore what’s outside your own city limits. Road trips are a great way to break out of your comfort zone and discover new places. By taking this route from Chicago to Kenosha, you’ll get to experience a little bit of everything, from charming small towns to world-class ski resorts. Plus, the Midwest is known for its friendly people and laid-back atmosphere, so you’re sure to feel welcome wherever you go. So why not hit the road and see where it takes you?