Northeastern Wisconsin’s Growing Bike Trail Network

In the deep woods of northeastern Wisconsin, near Michigan’s Upper Peninsula, a growing network of bicycle trails showcases the region’s villages and blue-green mosaic of lakes and forests. So far, 52 paved miles of the Heart of Vilas County Bike Trail wind through this lightly populated corner of the state, while on the county’s eastern side, the Great Headwaters Trail Foundation is building new connections that promise to expand the system even further.

“The most common experience I’ve had biking on the trail is the peacefulness of it,” said Mary Jones, a trail booster and director of the Chamber of Commerce for Boulder Lake, one of the five towns the trail runs through. “You’re in the woods surrounded by nature. You’re not worried about cars because you’re off the road. It’s beautiful.”

Jones’ town of Boulder Junction is the heart of the Heart of Vilas County Bike Trail System, which was begun here in 1994. The first piece of trail was a several-mile link connecting the town and a nature reserve. Soon, the trail expanded to a campground in the Northern Highland-American Legion State Forest, which sprawls 236,000 acres and holds 900 lakes. The lakes contribute to Boulder Junction’s claim to fame as the patented “Musky Capital of the World.”

From Boulder Junction, the trail heads west 16 miles to Manitowish Waters. This is Mary Jones’ favorite stretch to do on her Trek mountain bike. “There are a lot of pretty bridges overlooking waterways,” she said. “I really like to stop and take a break and enjoy the view.”

The trail doesn’t just pass through forests and lakes; it cuts through unexpected episodes of American history in this woodsy corner of Wisconsin. In Manitowish Waters, back in 1934, the Northwoods was a favored hangout for Chicago mobsters during the waning Prohibition era. An infamous shootout occurred that year at Manitowish Waters’ Little Bohemia Lodge, when FBI agents descended on the town hoping to arrest the notorious gangsters Baby Face Nelson and John Dillinger. Baby Face and Dillinger were indeed at the lodge, but the FBI agents made a tragic error when the lawmen began shooting into a vehicle carrying innocent diners from the Little Bohemia, killing one man. In the ensuing chaos, Baby Face Nelson killed an FBI agent before fleeing into the woods, where he hid out for several days at a remote cabin and was able to escape. Baby Face’s luck, however, would run out later that year in Chicago. Although a slight detour off the bike trail, the Little Bohemia Lodge remains open as a restaurant.

To the west of Manitowish Waters, at the trail’s terminus, superlative titles and gangster lore continue in Mercer, the self-described “Loon Capital of the World.” Mercer is home to Claire de Loon, a 16-foot-long likeness of the bird. Mercer’s next annual Loon Day will be on August 5th, 2026, and feature a loon calling contest. Mercer was also home to Ralph Capone, brother of the notorious gangster, who served time in prison for tax evasion with his brother’s criminal organization. Ralph had a place on Martha Lake, just outside of town, and either worked at or secretly owned local establishments like the Rex Hotel and Billy’s Bar.

As they attracted Ralph Capone, the region’s lakes continue to draw visitors whose spending in cabin country fuels the Vilas County economy. The bike trail is also proving to be a major boon to the county’s financial well-being. A recent economic impact statement commissioned by the local chambers of commerce found that 160,000 people use the trail annually, most of them coming from out of town specifically to bike. Trail users generate nearly $26 million in economic activity and $1.7 million in local tax revenue.

“Our economy is very dependent on tourism here. To put a number on what the bikers bring to our community was really great for us,” said Mary Jones.

At the eastern end of the trail system, the trail leads cyclists through the village of Sayner, population 207, where an innovation in snow sports occurred in 1924. Local mechanic Carl Eliason installed a rotating track and a 2.5-horsepower outboard motor on a wooden toboggan, creating the first modern, personal snowmobile. From Sayner, the trail turns south and follows the western shore of Big St. Germain Lake before turning along the lake’s south shore and entering the town of St. Germain.

East of the Heart of Vilas County system, and scant miles from the Upper Peninsula, a trail booster group called the Great Headwaters Trail Foundation recently completed an 11-mile section of trail between the towns of Conover and Phelps. The Foundation has several additional trails planned, including one they’re doing groundwork on presently that will connect with the Heart of Vilas County system in St. Germain. The headwaters the group’s title refers to are the Wisconsin River, which flows nearby and will eventually be traced by a bike trail.

Laura Van Valkenberg lives in Eagle River and is president of the Great Headwaters Foundation. “Our organization was formed 16 years ago, and our mission is to build family-friendly bike-pedestrian trails that will connect the communities in eastern Vilas County,” she said. (Her brother, Phil Van Valkenberg, used to write for Silent Sports.) “We could see on the west side of the county how wonderful the trails were and knew that it would be important for the eastern side of the county to replicate that. Not just from an economic tourism aspect, but for our residents and for our visitors.”

Great Headwaters finished its first stretch of trail in 2021 and is working on the connection between St. Germain and Eagle River that will link to the Heart of Vilas County network. “It takes a lot of effort to build a trail,” Van Valkenberg said. “People think this is easy—just pave it, and it should be done. It doesn’t happen like that. It takes a lot of effort to get municipalities to agree, takes a lot of fundraising to come up with the money. Trails are very expensive to build.” The Foundation covers the building expenses, and participating towns along the way handle regular upkeep. The Foundation hosts an annual fundraiser called Ride with Leine, featuring beer, brats, and a ride on the Conover-Phelps trail, led by Dick Leinenkugel of the Wisconsin brewing dynasty. The 2026 event will be on July 25th. Registration fees support the construction of more trails.

“I love biking,” said Van Valkenberg. “It’s such a great way to get exercise, fresh air, and enjoy the beauty of our county. I’m not a speed demon; I just love being out there and enjoying the surroundings. The trails are so fabulous, and I encourage anyone who enjoys biking to come explore them. The Heart of Vilas trails are nationally recognized because they’re phenomenal. The landscape is very picturesque, with many wooded areas and scenic lakes. Vilas has one of the highest concentrations of freshwater lakes in the world, so any of these trails offers beautiful views and quaint towns. It’s wonderful.”

Eagle River bills itself as the Snowmobile Capital of the World and has a competition called the World Championship Derby to back it up. Climate change, however, is shortening the snowmobile season, said Van Valkenberg, thus eroding an important economic pillar for the region. “We have to recognize that things are changing,” she said. “The window of time people can come north and recreate with snowmobiles is shrinking every year. Two years ago, snowmobile trails didn’t open a single day. Last year, they were open for a month. For local economies that rely heavily on tourism, they really need to consider expanding opportunities for silent sports, as silent sports recreation is growing. It’s important we look at providing places where they can do that safely. We need to move forward on these projects to provide that destination for people to come recreate and enjoy the beautiful north woods of Wisconsin.”