There’s a beautiful drive in eastern Wisconsin that people have been taking for a very long time – no matter the season. On the east side of Lake Winnebago in Calumet County, this drive traces the route of the of the old Wisconsin Military Road. It offers scenic vistas of the lake, while passing beautiful orchards, timeless supper clubs, and wild county parks. It’s one of the best scenic drives in Wisconsin, and here’s why.

Back in 1835-36, before Wisconsin was a state, the U.S. military built what was became known as the Old Military Road between Fort Howard (Green Bay) and Fort Crawford (Prairie du Chien).
https://www.alltrails.com/parks/us/wisconsin/high-cliff-state-park
It followed many trails originally used by Native Americans.
The 234-mile road was a primitive lane but it was the first highway in the state, and it was soon used by early settlers.
Facebook / Village of Stockbridge
Over the years, the road evolved into some of the highways that are well known to Wisconsinites today. In eastern Wisconsin, the route traces the shoreline of Lake Winnebago.
Throughout the year, the routes along eastern Lake Winnebago - Highways 151 and 55 - are traveled by people who love great scenery, and for good reason.
Facebook / Heritage Orchard
It passes through some beautiful agricultural land, including apple orchards. If you’re coming from the south, you can pick up the drive near Fond du Lac.

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If you find yourself hungry, you’re in the right place. This is supper club country, and you’ll pass gems like Jim & Linda's Lakeview Supper Club.
Facebook / Jim & Linda's Lakeview Supper Club
The highways travel through little towns and hamlets like Quinney, Pipe, and Stockbridge, and you’re never far from the lakeshore.
Facebook / Jim & Linda's Lakeview Supper Club
You’re also not far from some great parkland.
Alltrails / Anthony Scholfield
This side of the lake is home to Calumet County Park and High Cliff State Park, as well as Brothertown and Stockbridge Harbors, which are part of the county’s park system.

I used to live in this area of the state, and I always enjoy driving along the lakeshore – I think it’s one of the best scenic drives in Wisconsin. Let us know if you agree. Make your Wisconsin travel plans on Booking.com – and here’s where to find more Wisconsin attractions.

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Calumet County, WI, USA