Years before Wisconsin was a state, the United States spent $12,000 building a road through the Wisconsin Territory, linking Fort Howard in Green Bay with Fort Crawford in Prairie du Chien, passing through Fond du Lac, Portage (Fort Winnebago), and Dodgeville. It wasn’t a good road by modern standards, but it was a lot better than nothing. The 234-mile road was pretty rough, and it was swampy and even underwater during some times of the year. In some spots, there were large stumps impeding the passage of wagons. But it was the start of overland travel in Wisconsin, and it marked the start of a system of road travel that continues today.

Traces of the Old Military Road remain, and on one scenic trail, you can even travel it on two wheels. The Military Ridge State Trail is a destination that attracts thousands of cyclists every year – here’s why.

The Military Ridge State Trail runs through some pastoral countryside west of Madison in Iowa and Dane Counties.
Alltrails / Jennifer Rothamer
The trail’s route skirts the top of a long natural ridge that is the divide between the watersheds of the Wisconsin River and the Pecatonica and Rock Rivers. Long before Europeans arrived in Wisconsin, Native Americans traveled along this ridge.
Alltrails / Renner Anderson
The trail connects the communities of Dodgeville, Ridgeway, Barneveld, Blue Mounds, Mount Horeb, Riley, Klevenville, Verona, and Fitchburg. Most of these places are small towns, and the trail is very tranquil and peaceful. On some stretches, you’ll be far more likely to see cows than people.
Alltrails / Renner Anderson

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The trail is easy riding - most of it is crushed limestone, although there is a paved segment of the trail near Madison. Most of the route follows the former Chicago and North Western Railway corridor, which was built along the military road.
Alltrails / Greg Lerdahl
The railroad was first built on the ridge in 1880, and by 1982 the whole line was abandoned. The state quickly stepped in and purchased the railway property. Today, the trail is used for bicycling, hiking, snowmobiling, and cross-country skiing.
Alltrails / Renner Anderson
The trail passes near some major attractions in southwest Wisconsin, including Blue Mounds State Park and Epic Systems, a huge software company that offers tours of its whimsical campus.
Alltrails / Renner Anderson

A state trail pass is required for bicycling and in-line skating on the Military Ridge State Trail. Learn more about the trail on the state Department of Natural Resources website. After riding this scenic trail in Wisconsin, there are a lot of other adventures you can experience in the area, including this amazing trip underground.

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Featured Addresses
Military Ridge State Trail, 4350 Mounds Park Rd, Blue Mounds, WI 53517, USA