Winding Your Way Through the Small Towns Along the Great River Road

The Great River Road weaves alongside 250 miles of the Wisconsin bank of the shimmering Mississippi River. Wisconsin’s famous scenic byway runs like a heartbeat through 33 charming river towns, each with a little something special to offer for a cozy getaway.

Whether you’re looking to feel the wind in your hair or having a romantic getaway with your partner, driving down the Great River Road is a fun way to see the beautiful Wisconsin countryside, meet some down to earth people and make some unforgettable memories. Not sure where to start? Here is our suggested itinerary for the ultimate Great River Road Trip.   

Day 1 – Stockholm, Pepin, Alma and Maiden Rock

At the start of your journey on the Great River Road, you’ll find the quaint towns of Stockholm, Pepin, Maiden Rock and Alma.

The town of Alma has a lot to offer, and no offering is as breathtaking as the views at the end of the Buena Vista trail. This trail will make you break a sweat, but the scenic views of the Mississippi coursing through a brilliant green Eden, 500 feet up, are absolutely worth it. If you’re looking to enjoy the view but prefer to take a leisurely stroll, consider enjoying a hike at Mossy Hollow Trail, which offers a great view of the Mississippi Valley. If you’re looking to stay close to town, step into the rich history Alma offers by exploring one of the 10 Stair Step Streets scattered through the city. Dripping with Wisconsin history, these 19th-century stairways (also considered roads) are like stepping into a Jane Austen novel as you make your way to Main Street.

After a morning of hitting the trails, Pepin is waiting about 16 miles down the Great River Road. A picturesque little town in the big woods, Pepin is so much more than just the quaint farm town brought to life by its native author, Laura Ingalls Wilder. Peruse the Laura Ingalls Wilder Museum to learn more about the incredible author and the town that raised her. Then, come down from the little house on the prairie and splash into Pepin’s namesake—Lake Pepin. The birthplace of water skiing, Lake Pepin and the public beach that surrounds it is the perfect scene to soak up some sun, go fishing or enjoy a spirited game of sand volleyball. Try your hand at water skiing or take your significant other out for a dreamy sailboat ride out of the Pepin Marina to watch the lake shimmer in the sunset. Whether you’re looking for a splash of history or a golden tan—Pepin is the place to stop and take in a breath of fresh Wisconsin air.

Continue your countryside drive just a few miles away to charming and rustic Stockholm, a town well known for its arts and entertainment districts. Swing by some of the local shops like Sandy’s Clothing and Art, to find just the right accessories for an inspiring cooking class at Il Forno Ristorante, which is also a favorite local restaurant. You might even enjoy a fountain-side dinner there, with a glass of wine in hand in the piazza overlooking the Villa Bellezza Winery, where award-winning wines are crafted on-site with locally grown grapes from Villa Bellezza’s very own vineyard. If you enjoyed your memorable night out in this charismatic town, stop by The Palate—a gourmet kitchen store that offers a variety of cookware and dinnerware, so that you can recreate a little bit of Stockholm right in your own kitchen.

Round out your night at the historic Maiden Rock Inn, located just north of Stockholm. This historic B&B in Maiden Rock was originally built to be a schoolhouse in 1906 and has four unique, colorful rooms to choose from for a one-of-a-kind experience.

Day 2 – Trempealeau, Holmen, Stoddard and Onalaska

Start your morning bright and early with sunshine streaming on your face as you do yoga on the bluffs in Perrot State Park, near the town of Trempealeau. Paddle the canoe trail or hike the steep climb to the top of Trempealeau Mountain, where the panoramic eagle-eye view of the Mississippi River is unlike any other view offered in Wisconsin. Trempealeau offers an alluring bird-watching haven in its wildlife refuge that features over 200 types of birds during migrating season and an observation deck that provides an expansive view of the main pool area, where bald eagles, tundra swans, geese and ducks can be seen year-round. Consider enjoying Trempealeau’s natural scenic beauty and abundant wetland resources before you head out for more adventure on the Great River Road.

After a 13-minute drive to Holmen, you can enjoy the bluffs from the Drugan’s Castle Mound Country Club. The links wind around and between the bluffs, elevating your game. Whether you end with a double bogey or at par, your trip to this club is sure to be an ace. As a bonus, you can snap an iconic, starry-eyed Instagram picture, capturing the beauty of the moment in the dreamy Driftless Area — a slice of natural paradise right in the heart of Wisconsin.

If you’ve worked up an appetite at this point of your journey, let your hair down and drive on over to Stoddard’s Rocky’s Supper Club to pick up a true bite of Wisconsin — cheese curds. Stoddard has something to offer for every season, from fly-fishing in the summer to ice fishing in the winter. A small town with a big heart, Stoddard is guaranteed to have a friendly neighbor waving hello and alluring little shops that you’ll want to stop and check out.

End your evening on Onalaska’s waterfront at the Great River Landing, the best place to take a bike ride and enjoy the pastel hues of dusk as you cruise the Great River State Trail. With over 101 miles of trails to choose from, the town of Onalaska is nestled on a ridge with majestic scenery of the driftless region basins below. The steep rocky bluffs are THE place to muse while you enjoy a scenic picnic. Spend a serene night at the Lumber Baron Inn — a B&B right on the edge of Lake Onalaska, the ideal Shangri-La to fall in love with the lovely views of Wisconsin.

Day 3 – Prairie du Chien, Cassville and Dickeyville

As the Great River Road winds down to an end, pioneer an expedition to one of the first river towns established in Wisconsin: Cassville. Begin the day at Nelson Dewey State Park, a cool place to use a selfie stand to get the best views of you and your crew after you complete one of the five trails this park has to offer.
As you do, check out the different views offered throughout the park, culminating in the Stonefield Village Historic Site. If you want a stellar view of the haven in the Mississippi basin, register for the Cassville Ferry, proudly connecting two national scenic byways, the Great River Road and the Iowa Great River Road, since 1833.

At the southwestern intersection of Wisconsin and Iowa, just a 45-minute drive up the Great River Road (or a short ferry ride from Cassville), find even more classic riverside fare in Prairie du Chien. As the oldest European settlement on the Upper Mississippi River, Prairie du Chien has a little something for everyone. Take a tour of the historic Fort Crawford Museum and step into the battlefield to watch a reenactment of the only battle of The War of 1812 in Wisconsin. If you’d like a more peaceful setting, stroll along the beautiful terrace on the Villa Louis Estate while enjoying a couple’s dreamy getaway in a restored Victorian mansion. Satisfy your appetite like a local at a Prairie favorite, The Depot, where you can enjoy a refreshing Wisconsin-brewed beer while marveling at the restored train station features The Depot offers.

At the end of the Great River Road is the apex spot to stop and take the ultimate road trip photo at The Grotto and Shrines in Dickeyville. The shrines are located on Holy Ghost Parish grounds and were created from a multitude of materials including stone, glass, gems and seashells, which the pastor collected from all over the world. Learn about the eccentric history of the Insta-worthy attraction and add a few snapshots to your trip’s photo album that will make your friends ask you how they can get there too.

The Great River Road’s small towns of Wisconsin have an endless supply of unforgettable things to do. If you’re looking for even more options for your next weekend getaway, here are some more road trip destinations through Wisconsin’s leg of the Mississippi River.