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Winona Bluff Loop

Winona Bluff Loop is 65.2 miles of loop riding through Winona County in Minnesota — Bluff Country, the Root River valley, the Mississippi bluffs and the ridge roads above them. Moving time is about 87 minutes; allow 125 with stops — a full day. It is scored CS-3, Spirited: 88 corners, 148° of turning per mile, 2,758 feet of climbing. The roads it uses, in the order you ride them, are in the app.

Curviness
CS-3Spirited · 1.35/mi
Distance
65.2 mi87 min riding
Corners
8845% sharp · Mixed
Climbing
2,758 ft43 ft/mi · Hilly
Shape
LoopFull day
Roads
Backroads89% county & local
Traffic
525vehicles a day, median
Speed limit
65 mphtypically 55
Open this route in the app

About this road

Winona occupies a dramatic bend of the Mississippi, framed by high bluffs that have drawn people for generations. Sugar Loaf, the residual rock pillar shaped by quarrying and erosion, is the city’s most recognizable landmark. This loop explores both the river edge and the quieter agricultural ridges inland. Any of the public overlooks supplies the classic Upper Mississippi prospect; the inland roads supply the sense of the broader Bluff Country. The full-day length allows a complete circuit from river to upland and back, with enough climbing to make the elevation tangible. Winona’s services make logistics easy; the surrounding country provides the solitude and scenery. The route captures the essential tension of the region—urban river corridor and rural dissected plateau—in a single coherent day. Start by the water at Winona, climb into the hills, return with the big views still in your head.

How it rides

88 corners over 65.2 miles — 1.35 a mile, and 148° of turning for every mile ridden. That scores CS-3, Spirited on the five-point curviness scale. 45% of those corners are sharp ones, and the road reads as mixed.

What it climbs

The road climbs 2,758 feet in total, 43 feet per mile, between 642 and 1,348 feet — 706 feet of relief. The longest single climb is 513 feet over 1.8 miles, and the steepest grade on it is 9.1%. By Driftless standards that is hilly.

Surface, speed and traffic

Paved end to end. 89% of it is back road rather than highway, the other 11% state or US route. Posted speeds run to 65 mph, typically 55, measured across 25% of the route. Where traffic counts exist — 32% of the miles — the median is 525 vehicles a day, busiest at mile 1.4 with 17,430.

Where to stop

1 of the towns on this road has somewhere to stop — 6 fuel, 4 food, 3 bars.

Longest stretch without fuel: 65.2 miles. Worth knowing before you set off if your tank is small.

Listed alphabetically, and chosen by us rather than rated by anybody. The order you reach them, and the mile each one sits at, are in the app.

Worth knowing

Turn-by-turn directions and the spoken guidance are in the app. Every figure on this page is measured from the route itself — corner counts and gradients from the road geometry, elevation from the national elevation dataset, traffic from the state transport departments where counts exist.

Nearby roads