3 Wisconsin Cities Perfect for a Quick Weekend Getaway

Days off in the summer are precious, we know. And we also know that you don’t want to waste them waiting in lines, spending big bucks, and going to run-of-the-mill attractions.

Luckily, the Badger State is full of hidden gems and summer activities that are worth your while, whether you’re in the big city or a tiny coastal town. 

So without further ado, here’s a curated itinerary for quick weekend trips to La Crosse, Milwaukee, and Bayfield. 

Take advantage of the uncommon peace and quiet in La Crosse

Being a proper college town, La Crosse is buzzing with teenagers and twenty-somethings for most of the year. However, it becomes much quieter once the kids head home for summer break, making it the best time to visit. 

Start your staycation off right with a trip up to one of La Crosse’s picturesque bluffs. You can get to Grandad Bluff by car, while the others require a bit of hiking. Either way, you’ll get breathtaking views of the city, riverfront, and marshes—all while surrounded by a beautiful array of wildflowers. 

After working up an appetite, we recommend hitting up Rudy’s Drive-In, which opened in 1933 and features roller-skating carhops to this day. Whether you get a cheap chili dog, the Historic Trempealeau Hotel Walnut Burger, or a banana split, you can’t go wrong with this menu. 

If you have little ones with you, the Children’s Museum of La Crosse is a great post-lunch activity. It’s reasonably priced, full of interactive exhibits, and big enough to spend a few hours in but not so big that it draws massive crowds. 

Alternatively, you can check out the Dahl Auto Museum or take a tour of the Romanesque Mary of the Angels Chapel.

No need to make a dinner reservation; hop aboard a classic paddlewheel boat instead. La Crosse Queen Cruises offers two different dining options; the popular Saturday Dinner Cruise, which offers live music and chef-carved prime rib and chicken, is perfect for date night, while the cheaper Pizza Cruise is great for the whole family (and there’s unlimited beer!). Either way, you’ll get gorgeous, golden-hour views of the Mississippi.

Stay the night at The Charmont, a renovated candy factory along the river that offers eight exquisite rooms as well as a French-inspired restaurant, café, bar, and rooftop terrace. Before hitting the hay, head up to the roof for a nightcap (Wisconsin Mule, anyone?).

The next morning, grab a coffee (made with sustainable, local, and organic ingredients) from the hotel’s café and take a stroll along the river before checking out. While you’re out, pick up all the fixings for a picnic at Pettibone Park.

In the afternoon, take your crew brewery hopping instead of visiting the world’s largest six-pack (a kitschy tourist haven). If you feel like kicking it up a notch, set out on the craft beverage trail, which hits four breweries, 10 wineries, and one distillery. 

One of the best ways to maneuver the map is to rent a bike from the Drift Cycle Community Bike Share Program. With 15 different docking stations across the city, finding a bike and returning it when you’re done is super simple. 

After spending two days in this delightful riverside city, we’re sure you won’t want to leave!

Enjoy a slice of city life in Milwaukee

As a local Wisconsinite, you might avoid your state’s big cities like the plague. However, Milwaukee is popular for a reason! It just takes a bit of creativity to come up with an itinerary that’s full of summer fun but devoid of tourist traps.

Instead of picking any old weekend to visit, you might want to plan your trip around one of Milwaukee’s many summer festivals; it is called the City of Festivals, after all! But instead of flocking to a nationally recognized food or music festival, pick a quirky gathering where you can meet locals, enjoy interesting cuisine, and celebrate eccentricity. 

Afterward, watch the sunset from one of the many rooftop bars. Located in the city’s historic Third Ward, The Outsider offers craft cocktails and skyline views. If you’re more of a beer guy or gal, check out the rooftop terrace at Good City Brewing. 

As far as where to go to catch some Z’s, there are tons of unique Airbnb locations to choose from. For families or larger groups, we recommend this grocery store-turned-arcade.The highly reviewed house features a spectacular view/location, five bedrooms, and hundreds of games. If you’re traveling as a couple, why not give glamping a go? You can book a classic Airstream in the hip Bay View neighborhood and get access to the entire camper and backyard, complete with a fire pit and grill! 

Start off day two by getting active al fresco. There are several spots for outdoor yoga that offer classes throughout the summer, including Villa Terrace Decorative Arts Museum. Every Sunday morning, you can partake in a free hour of guided yoga on the terrace with gorgeous views of Lake Michigan. 

For lunch, head to Milwaukee Public Market, where you can order from over a dozen different vendors, from local cheese and meats to authentic Mediterranean food. You have the option to eat your food on the rooftop garden or have yourself a riverfront picnic.

Instead of walking along the city’s packed sidewalks, rent a paddle board or kayak and see it from the other side. There are various companies, watercraft, and locations to choose from (primarily Lake Michigan or the Milwaukee River). Additionally, you can opt for a guided tour or explore solo!

Then, instead of paying to get into one of Milwaukee’s renowned art museums, take a stroll through Black Cat Alley. There, you can gaze at 21 murals by 24 artists from across the globe and enjoy other creative activities without paying a dime! This is also the perfect place to take some vacation photos—because we’re fairly certain you won’t want to forget this trip. 

Embark on huge adventures in the tiny town of Bayfield

Although Bayfield is officially the smallest city in all of Wisconsin, it’s arguably one of the best. Don’t just take our word for it—Conde Nast Traveler named it one of “The 23 Best Places to Go in the U.S. in 2023.”

Known as the “Gateway to the Apostle Islands,” this charming city borders Lake Superior and offers a ferry service that makes several daily trips to the nearby Madeline Island. 

You can take your pick from a variety of historic bed and breakfasts, but two of the best are Pinehurst Inn (which comes with a three-course home-cooked breakfast) and Old Rittenhouse Inn (​​Wisconsin’s first country inn and gourmet restaurant). 

Before checking in, consider berry picking at one of the area’s six local berry farms. Make sure to check the Orchard Report to find out which fruits are ripe at the time of your stay, but you can expect to pick your own strawberries, raspberries, and blueberries throughout the summer. 

When it comes to grub, this city has many local restaurants to choose from—and not a chain in sight! The highly rated Maypenny Bistro, which offers “American food with a Turkish flare,” is known for its friendly service and delicious food (including white fish livers, the local specialty). Pier Plaza Restaurant offers great views and a fish fry every Friday. Lastly, The Copper Trout has the best surf-and-turf around.

For travelers who are 21 and up, we recommend heading up the road to Copper Crow Distillery, the first Native American-owned distillery in the country. Sip on artisan cocktails in the tasting room or by a fire pit on the patio. 

Then, douse yourselves in bug spray and enjoy some live, outdoor music in the evening. For free and local tunes, head to Concerts By the Lake, and to see big-name artists (like Marty Stuart!), check out Big Top Chautauqua. 

After a restful night’s sleep, spend the second day exploring the Apostle Islands. Hop aboard the Madeline Island Ferry Line for a 25-minute scenic ride to the largest of the 22 islands. You’ll get dropped off at La Pointe, which hosts a ton of walkable activities, from art galleries and gift shops to quirky dive bars like Tom’s Burned Down Cafe. 

Spend the rest of the day basking in the sun at one of the three public beaches or exploring the sea caves on a rented paddleboard. Adventure Vacations has a variety of tours and watercraft to choose from. If you prefer to stay on land, there are beautiful hiking trails in the Madeline Island Wilderness Preserve and the Big Bay State Park. 

The island life is calling!