The Driftless Area, known for its rolling hills, steep bluffs, and winding river views, offers some of the most picturesque driving routes in the Midwest. Whether you’re looking for panoramic river vistas, charming small towns, or lush forests, these driving tours will immerse you in the natural beauty of the Galena region and beyond.
Tour One: Mississippi River Scenic Byway
Start your day by heading south from Chestnut Mountain Resort and joining the Great River Road National Scenic Byway, one of America’s most iconic routes. This drive will take you along the Mississippi River, offering stunning views of the river’s twists and turns framed by dramatic limestone bluffs. As you drive, you’ll pass through charming river towns like Hanover and Savanna, where you can stop to explore local parks or enjoy riverside dining.
In Savanna, take a detour to visit Mississippi Palisades State Park, where you can park and walk to scenic overlooks that offer breathtaking views of the Mississippi River valley. The rugged cliffs and dense forests provide a stunning backdrop to your drive.
Tour Two: Elizabeth and Hanover Loop
For a shorter day trip, take the scenic route to Elizabeth, Illinois, located just 20 minutes from Chestnut Mountain. This peaceful drive takes you through rolling farmlands and quiet countryside. In Elizabeth, you can visit Apple River Fort for a bit of local history, or stop by the Grand Antique Company for unique shopping.
From Elizabeth, head south toward Hanover, a charming small town known for its outdoor recreational opportunities. The nearby Wapello Land & Water Reserve offers beautiful trails and wildlife viewing, perfect for a break from driving. Continue along scenic backroads that wind through forested areas and pastures, bringing you back to Chestnut Mountain Resort.
Tour Three: Wisconsin River Towns Tour
Cross the river from Galena and head into Wisconsin for a delightful drive through quaint river towns. Start by driving northwest from Chestnut Mountain to Potosi, Wisconsin, home to the historic Potosi Brewery and National Brewery Museum. After a brewery tour, take a leisurely drive along the Wisconsin side of the Mississippi River, where the hills and valleys create a beautiful tapestry of scenery.
Further north, stop in Cassville, Wisconsin, a small town known for its ferry service across the river. Enjoy a peaceful drive along County Road VV, which follows the river bluffs and offers occasional glimpses of the Mississippi’s wide expanse. This route will bring you to Prairie du Chien, another charming river town with historical significance and scenic beauty. After exploring, you can return to Chestnut Mountain via the Great River Road, ensuring your day is filled with spectacular views.
Tour Four: Tri-State Overlook Route
If you want a drive with panoramic vistas, head east from Chestnut Mountain toward Horseshoe Mound Preserve. Located just outside of Galena, this scenic spot offers views where Illinois, Iowa, and Wisconsin meet. Continue along the winding country roads of Stagecoach Trail to enjoy more expansive views of the tri-state area’s rolling landscapes.
For a relaxing break, stop in Shullsburg, Wisconsin, a picturesque town with a rich mining history. Visit the Badger Mine and Museum, or simply wander through the historic downtown filled with small shops and cafes. Afterward, take the backroads through lush valleys and forested hills to return to Chestnut Mountain.
Tour Five: The Driftless Adventure
For an all-day adventure, embark on a journey through the heart of the Driftless Region. Begin your tour by heading north into Wisconsin and winding through Sinsinawa Mound, a peaceful retreat center known for its walking trails and scenic views. From there, follow County Road Z northward through the Driftless Area’s distinctive landscape of rolling hills and deep valleys.
Stop in Dickeyville, home to the unique Dickeyville Grotto, a folk art treasure built from stone, glass, and other materials. Continue north to Mineral Point, where you can explore historical architecture and art galleries, and then circle back through Shullsburg before returning to Chestnut Mountain.
Return to Chestnut Mountain to Relax
After a day of exploration, return to Chestnut Mountain Resort and unwind with spectacular sunset views over the Mississippi River. Relax in the comfort of the resort’s accommodations, dine at The Summit Food & Spirits or take advantage of seasonal on-site activities.
Each driving tour offers something unique, whether it’s breathtaking river vistas, charming small towns, or hidden gems waiting to be discovered. With Chestnut Mountain Resort as your starting and ending point, you can explore the best scenic drives the region has to offer, all while enjoying the resort’s exceptional comfort and hospitality.
