Winona County: River Trails, Bluffs and Culture

The Mississippi River Trail runs through Winona County and includes scenic sections of state, regional and local trails. State and federal hiking and water trails in the county also include the waterways of the Upper Mississippi River National Wildlife and Fish Refuge. For planning your trip, the highlights are easy to distinguish: trails and bluff-top views alongside art, mill history and architecture.

Hiking, Biking and Climbing Trails

Bluffside Park has a 15-mile network of multi-use trails, with views of the Mississippi River Valley from the bluffs. The trails are designated for mountain biking, hiking, skiing and snowshoeing year-round. In the same park, Oberton Family Bike Park offers a toddler track as well as jump and drop lines for riders from beginner to advanced.

Sugar Loaf has 38 protected climbing routes and a multi-use trail to the summit, with expansive views of the Mississippi River Valley. Winona Ice Park is an artificial ice-climbing park in Sugar Loaf Park, high above the Mississippi. Sugar Loaf thus offers both climbing routes and a park specifically dedicated to ice climbing.

The Flyway Trail – Winona Connector links Winona with Buffalo County, Wisconsin. Its route crosses the Highway 54 Interstate Bridge, the John A. Latsch Historical Wagon Bridge and an 842-foot-long railroad bridge. Lake Park offers a different kind of route: a roughly five-mile, flat and easy-to-ride paved trail runs through the park and loops around both sections of the lake. While the Connector links two places, the Lake Park trail is a loop around the lake.

Art and History

Pickwick Mill was built by Thomas Grant and Wilson Davis on Big Trout Creek from 1856 to 1858. It is one of the oldest water-powered grist mills in southeastern Minnesota. The Minnesota Marine Art Museum explores humanity’s historic and ongoing relationship with water. Its six galleries display more than 600 works of art on a seven-acre campus on the Mississippi.

The Winona County History Center is housed in a historic 1915 National Guard building and is complemented by the contemporary Laird Norton Edition. Another museum of the Winona County Historical Society opened in 2017 at the Winona County Fairgrounds in St. Charles. Its exhibits on Winona County’s agricultural history include an exhibition building, the Gainey-McCarthy Schoolhouse, the Hill sisters’ log cabin and an early log barn.

The Winona Downtown Commercial Historic District includes more than a hundred sites listed in the National Register of Historic Places. It is also Minnesota’s largest collection of Victorian commercial architecture on the Mississippi. A walking tour of historic downtown Winona passes through nearly a dozen preserved blocks listed in the National Register. The digital tour “Winona’s Glorious Glass” also lets you visit the featured sites in person.

Bunnell House is a home built around 1850 in the Rural Gothic or Steamboat Gothic style and listed in the National Register of Historic Places. The two terms describe its architectural style, while the National Register listing also marks the home’s historic status.

Landscape and Local Traditions

Winona State University’s Landscape Arboretum includes more than 125 acres of university grounds and nearby wooded bluffs. Winona’s annual Tundra Swan Watch also draws many visitors. It offers a seasonal contrast to the year-round trails designated at Bluffside Park, without requiring you to plan your trip for any particular season.

The Winona County Fair has brought people together since 1858 and is an annual, family-friendly outdoor festival. Garvin Heights Vineyards offers a different perspective on the local landscape: the vineyard makes wine from cold-hardy grapes grown on its own hillside farm above Winona, along the Mississippi.

The Winona Visitor Center offers brochures, maps, souvenirs, travel advice and information about Winona. For planning your time in the area, check the latest visitor information. This can help you decide whether to focus on trails and scenery, historic sites, art or local traditions when shaping your trip.

Discover more destinations: Winona, Carver, Aitkin County, Roseau, Hennepin, Le Sueur County, Washington, Dodge County.

View the broader travel guide: Minnesota.