Expect the Unexpected: 5 Out-of-the-Ordinary Experiences in Pepin, WI

Perched at the edge of the wide expanse of the Mississippi River, Pepin is one of the many tiny communities (33, to be exact!) dotting Wisconsin’s Highway 35, also known as the Wisconsin Great River Road. The route is marked by steep, forested valleys, plenty of soaring limestone bluffs, and some of the most incredible river views in the state.

Even though the village of Pepin is home to fewer than 1,000 residents, there’s no shortage of things to do and see. If you and your road trip crew are looking for extraordinary fun on your River Road tour, these five delightfully surprising activities are waiting for you in Pepin.

A Hot Air Balloon View of the Mississippi River

Sure, you can explore the Mississippi River by boat—but why not upgrade to a hot air balloon? For a bucket list experience you won’t find anywhere else, round up a few of your friends and family and head to Lesmeister Balloon Company. You’ll be in good hands with owner and pilot Mike Lesmeister—also known as “The Flightmeister.” His decades of experience, coupled with a true passion for this peaceful, soaring transport, means you’ll also learn a thing or two about hot air balloon operation as you drift over unforgettable views.

A Taste of Italy, Wisconsin-Style

Lesmeister’s balloons are launched in a field just north of Villa Bellezza Winery, which is the perfect place to relax and regroup with loved ones. An old-world winery and vineyard experience, Villa Bellezza was designed to resemble a small Italian village, complete with acres of wine grapes grown on-site as well as a tasting room, restaurant and stunning stone piazza. For those looking to learn about the winemaking process, the winery offers tours during the summer months. Don’t forget to stop at La Fontana—the large fountain at the center of Villa Bellezza’s piazza—and make a wish by throwing in a coin.

Step Into a ‘Little House on the Prairie’ Book

American writer Laura Ingalls Wilder was born in Pepin, and the history of her family is alive and well in the village. Fans of Wilder can visit the Wayside Cabin. The cabin, built on three acres of Wilder’s birth site, is a stunning reproduction of the Little House in the Big Woods cabin in the book of the same name. After touring the cabin, visit the nearby Laura Ingalls Wilder Museum, where you can explore what life might have been like for Wilder and her family in the 1870s.

It’s a lake. It’s a River? No, it’s both!

Lake Pepin is proof that a body of water can be both a river and a lake. Located in a valley that was carved by the outflow of an enormous glacial lake at the end of the last Ice Age, the lake was formed when the Mississippi River was partially dammed by a delta from a tributary stream. The result is a 40-square-mile lake famous for a variety of recreational water activities—not to mention being the “Birthplace of Waterskiing.” In 1922, local teen Ralph Samuelson fashioned a homemade pair of skis and got behind a boat on the lake to make history. Get out on the lake by visiting Pepin Sailing School and Charters, located seasonally at Pepin City Marina. 

Unique Lakeside Foodie Spots

Pepin has plenty of hidden gems when it comes to food and drink, too. Choose your own adventure at The Garden Pub and Grille where you can enjoy a malt or shake courtesy of their on-site ice cream shop or get transported to the tropics courtesy of their authentic tiki bar and outdoor terrace. No matter your drink order, make sure you stop by the Pub’s big yellow chair and grab a photo to document your experience!

Or, if you’re looking for a little history with your lunch, explore the Pickle Factory Waterfront Grill. Originally built on the shores of Lake Pepin in the early 1900s to manufacture pickles and sauerkraut, this spot has been lovingly restored and is a favorite with visitors and locals alike. Make sure to try their famous fried pickles or their Pickle Flatbread with plenty of pickles, cheese and Canadian bacon. During the summer months, boaters can take advantage of the restaurant’s 280-foot dock—giving a whole new meaning to drive-up service!

Wondering where to stay near Pepin? Explore our directory to find the perfect place for your Great River Road getaway.