This ride takes you on a journey through the picturesque bluff country of southeastern Minnesota & western Wisconsin – passing horse farms and hay fields, traveling through river bottom and railroad settlements, traversing creek gullies and wooded ravines, and rolling along the shoreline of the Mississippi River and the grand Lake Pepin.


A mecca for MN day-trippers, the undulating and relatively curvy bluff country roadways are typically kept in good condition on both sides of the river by MNDOT and WisDOT. Nevertheless, be wary of gravel in the corners, wildlife, and slow-moving vehicles and farm implements.


Closest motorcycle dealerships are Red Wing Motorsports and Harley-Davidson Shop of Winona.


Red Wing
The entire city of Red Wing has been placed on the National Trust for Historic Preservation, so it would make sense that you start your trip at the St. James Hotel, a building that dates back to 1875 and the early days of this bustling riverside community. Park your bike alongside the town’s train station, located on Levee St. behind the hotel, for a good photo op.

Lake City
Approx. 17 miles southeast of Red Wing, along the shoreline of Lake Pepin, Lake City was the home of the inventor of waterskiing, Ralph Samuelson, and is thus known as “The Birthplace of Waterskiing.” Stop at the southside sailboat marina for a photo op.

Carley State Park
Once past the farm community of Plainview, you’ll be approaching Carley State Park. Have your two-piece fishing pole along? The Whitewater River is a designated habitat for brown trout. In May, you can find Bluebells and other wildflowers that provide a carpet of color on the forest floor. Rustic campsites are located near the picnic area.

Whitewater State Park
If you didn’t stop at Carley State Park, you’ll find Whitewater State Park just south of the community of Elba. Here you can find brown, brook and rainbow trout, a sandy swimming beach, camping and a year-round visitor center.

You’ve now passed the farm communities of Altura and Rollingstone and dropped down through the blufflands to Winona.

Named after Princess We-Noh-Nah, daughter of Chief Wapasha, and nicknamed The Island City because its original plat was located on a sand bar of the Mississippi River, Winona’s growth was built on railway and steamboat transportation, wheat milling and lumber.

Settlers arrived in the area in the early 1850s following the signing of the treaties of Traverse des Sioux and Mendota. Winona was incorporated as a city in 1857, in 1858 became the site of the first “normal” school west of the Mississippi via the establishment of Winona Normal School (now Winona State University), and by 1860 was the third largest community in Minnesota.

The city’s most noticeable physical landmark is Sugar Loaf – a lighted, rocky pinnacle that arises from one of the many bluffs that line Hwy 61.

Fountain City
Now in Wisconsin and headed north on WI-35, you come across Fountain City – originally called Holmes’ Landing after Thomas Holmes, who settled there in 1839. Boats would stop at the landing to take on firewood, as well as water from springs not far from the river. On the northwest side of the city, Eagle Creek flows around the base of Eagle Bluff, one of the tallest bluffs along the Mississippi. Travel another 2.8 miles north to visit Merrick State Park for a picnic, spring water, camping, access to fishing opportunities, or just a chance to stretch your legs.

Pass Buffalo City and ride into Alma, located next to Lock & Dam Number 4 on the Mississippi River and a major nesting area for bald eagles. Alma’s city motto beckons visitors to “Step into Living History.” Stop by the Castlerock Museum, a collection of arms and armor from the times of the Romans to the Middle Ages.

Travel 8.6 miles north from Alma and arrive in Nelson, located at the junction of the Mississippi River and Chippewa River valleys. The village’s primary destination for tourists is the 100-year-old Nelson Cheese Factory. This is the title destination of this “Mississippi Cheese Run.” A causeway and bridge across the Mississippi link Nelson with the city of Wabasha, MN.

The author Laura Ingalls Wilder was born in the Pepin area, 7.8 miles north of Nelson. The village celebrates this every September with traditional music, craft demonstrations, a “Laura” look-alike contest, spelling bee and other events. The Little House Wayside is located 7 miles northwest of the village.

Maiden Rock
Maiden Rock, 12.7 miles north of Pepin, is named for a cliff just south of the village. In the Princess Winona legend, the daughter of Dakota Indian Chief Red Wing jumped from this cliff after her lover was killed under orders from her father. Park your bike and find the plaque that stands near the base of the cliff.

Finish your ride by traveling 12.8 miles to the unincorporated Hager City and utilize Hwy 63 to return back across the Mississippi River to Red Wing.


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