Small-town charm. Mississippi River views. Supper clubs and Bloody Marys. And yes—a college bar crawl we didn’t see coming.

Mississippi River Bridge, La Crosse, Wisconsin

La Crosse, Wisconsin might not have been on your radar—but after a spring weekend spent there with my husband, I can say: it should be.

Just about 4.5 hours from Chicago, this Mississippi River town is the kind of place that sneaks up on you in the best way. It’s got scenic bluffs, a walkable downtown, local shops and breweries, and a buzzing college-town energy thanks to the University of Wisconsin–La Crosse.

Here’s how our weekend played out—plus ideas for how to make it your own.

Friday: Supper Club Nostalgia at Ishnala

We broke up the drive from Chicago with a stop at Ishnala Supper Club, a Wisconsin institution tucked into the trees just outside Wisconsin Dells.

Overlooking Mirror Lake, Ishnala blends vintage supper club charm with natural beauty. The land has a rich history—it was once ceremonial ground for the Winnebago Tribe and later became a trading post and cabin before transforming into one of Wisconsin’s most iconic dining spots.

Inside, the wood-paneled interior, stone fireplaces, and lake-facing windows feel like stepping back in time. They’re known for their Old Fashioneds (truly iconic), and since the wait was already well underway, we grabbed seats at the bar—a genius move, because we got the best view of the sunset. A plate of cheese curds and prime rib skewers later, we were happily road-trip refueled and ready to finish the drive to La Crosse.

Staying Outside the City: A Tiny House Retreat

For this trip, we booked a Scandinavian-inspired tiny house just 15 minutes outside downtown La Crosse. Set on private wooded land with access to hiking trails, the home was simple, peaceful, and beautifully designed.

There’s a full bath, kitchenette, and space for two to sleep comfortably, with seasonal access to a saltwater pool. Waking up to fresh air and the sound of nearby chickens was a pretty delightful change of pace from the city.

If you’re someone who likes to unplug a bit on the weekends (but still wants to be close to good food and coffee), this kind of stay strikes the perfect balance. (Did you know The Weekend Discovery can also book homes?).

Saturday: Antiquing & Unexpected College Nostalgia

One of my favorite things to do on road trips is go antiquing—you can find the most unique pieces that instantly become travel mementos. La Crosse has a few great spots for vintage finds and secondhand gems, and I left with a few treasures I didn't even know I needed, albeit I had to do a bit of searching. I found items at both The Antique Center of La Crosse and Caledonia Street Antiques.

From there, we wandered downtown and unintentionally found ourselves smack in the middle of a college senior bar crawl (UW-La Crosse, we see you). It was loud, it was chaotic, and honestly? It was fun.

We stopped into Del’s Bar, a local classic since the 1930s. Known for their Bloody Marys and come-as-you-are vibe, it was the kind of place that instantly felt familiar.

If the weather had been a bit nicer, I would’ve loved to explore more of the bluff trails or rent bikes along the river. La Crosse feels like the kind of place where being outdoors is half the experience.

Bonus Stop: The Charmant Hotel

Because I love scouting great hotels for my clients, I made a stop at The Charmant, a 67-room boutique hotel in the heart of downtown.

The hotel sits on the site of La Crosse’s very first settlement, and the building itself used to be the FUNKE Candy Factory. Today, it’s been transformed with exposed brick, maple floors, and elevated French-inspired design—perfect for a romantic weekend. I was impressed by the design and the quality of the fixtures.

Even if you don’t book a room here, stop in for dessert (yes, there’s still candy!) or a cocktail on the rooftop terrace in warmer months. Book with The Weekend Discovery for exclusive perks and ammenities.

Sunday: Drive home with a Madison Detour

Instead of driving straight home, we made a stop in Madison, Wisconsin for lunch at Great Dane Pub & Brewing. Madison is a fantastic road trip pairing with La Crosse—it’s known for its lakeside trails, progressive vibe, and great local food.

If you’ve got time, stroll around the Capitol Square, browse indie bookshops, or hit Olbrich Botanical Gardens. And if it’s Saturday? The Dane County Farmers’ Market is one of the best in the Midwest.

Why La Crosse is a great Midwest Weekend Getaway

It’s the kind of place that feels just under the radar—and that’s what makes it special. You’ll get river views, quirky shops, plenty of good food, and a feeling that you’ve stumbled onto somewhere a little bit undiscovered.

It’s perfect for:

Couples looking for something scenic but low-key
Friends’ trips that want equal parts fun + fresh air
Families who want hikes, riverside parks, and a kid-friendly downtown
Solo escapes with time to read, recharge, and explore at your own pace

Plan Your Own La Crosse Weekend

Whether you’re into antiquing and ice cream, suppertime throwbacks, or impromptu bar crawls, La Crosse offers a weekend full of surprises—and some seriously good views.

Want help planning your route, stay, or stops along the way?
The Weekend Discovery is here to make your next getaway seamless (and way more fun). Submit an inquiry here.

Weekend Getaway from Chicago: Discover La Crosse, Wisconsin