Old Plank Road Trail: Plymouth to Sheboygan

Over the course of 10 miles from Plymouth to Sheboygan, this section of the Old Plank Road Trail journeys through rural countryside and farmland. Along the way it passes Sheboygan Falls and Kohler. This segment of the trail is the most popular. Although it’s the flattest section, it still includes a few small hills. The trail surface is paved, in very good condition.

The Plymouth trailhead is on the east side of town, on County Highway C. It has a parking lot, picnic shelter, cooking grills, pit toilet, garbage/recycling bins, and free library stand. A stone monument commemorates the construction and use of the old plank road.

To reach the trailhead by car from Wisconsin State Highway 23, take the Plymouth exit south onto Wisconsin State Highway 57. Drive 0.6 mile, and turn left (east) on County Highway C. The trailhead entrance is on the left (north) side of the road after 175 yards.

Trail-goers looking for a bite to eat in Plymouth have numerous options. Near the trailhead is the Roadside Bar and Grill, a popular restaurant with sandwiches, gyros, and burgers. Their full menu also includes a Friday fish fry. Chester’s Drive-In features carhops who take orders from vehicles. Chester’s offers its root beer freeze, ice cream treats, burgers and fries.

Known for its cheese industry, Plymouth was the home of the National Cheese Exchange from 1918-1956. The city titles itself “Cheese Capital of the World,” and currently has four cheese processing facilities. Plymouth’s downtown is decorated with large murals reflecting its past. Many of the historic buildings in downtown have been restored. Today, museums, restaurants, antique and specialty shops make Plymouth an attractive city for visitors.

This area was first known by Native Americans as Quit Qui Oc, or Crooked River. The city was surveyed in 1835, and settlement by white Americans and European immigrants began in 1845. Plymouth incorporated in 1877, known as “Hub City.” The name came from its central location in Sheboygan County, or because the city housed the Schwartz brothers wagon shop in the 1860s.

Back at the trailhead on County Highway C, a spur trail travels north for a half mile along Wisconsin State Highway 57 to the junction of the Old Plank Road Trail. The intersection is marked by a welcome sign. The westward path crosses the highway and heads to Fond du Lac. Continuing east on the path takes bicyclists toward the trail’s end in Sheboygan.

From the intersection, the Old Plank Road Trail continues north and then turns east to journey next to Wisconsin State Highway 23 for the remainder of the route. It’s a half mile from the trail junction to Willow Road. Along the way, the path crosses a branch of the Mullet River. It also passes a large pond to the south, where benches allow trail-goers the chance to rest and take in the view.

It’s 2 miles from Willow Road to Bridgewood Road. The trail crosses County Highway M and Hillside Road in that span. The route passes farm fields, and is relatively flat with a few rolling hills. Covered picnic tables and benches are found here and along the entire route.

Over the next 1.7 miles from Bridgewood Road to the Sheboygan River, the elevation drops by 50 feet. The path crosses Sunset Road and County Highway TT before arriving at the river crossing. The trail then climbs slightly over the next half mile to Meadowlark Road and a trailhead. Situated by the Sheboygan River, this trailhead also serves as a canoe/kayak launch. The trailhead has a parking lot, pit toilet, handpump well, and garbage/recycle bins.

This trailhead is easily accessed by car from Wisconsin State Highway 23. Turn south onto Meadowlark Road and then right (west) into the trailhead parking lot. Meadowlark Road is about 5 miles east of Plymouth and one mile west of Sheboygan Falls.

The Old Plank Road Trail continues eastward over gently rolling hills for one mile. After passing a covered picnic shelter, the trail crosses Wisconsin State Highway 32. A spur trail next to the state highway leads south into Sheboygan Falls. Trail-goers looking to visit Sheboygan Falls, find a meal, or rest area may want to consider taking the spur trail. Near the trail are both the Falls Café and the Bicycle Works bike store.

The name of Sheboygan Falls comes from the series of falls on the Sheboygan River. Originally called “Rochester,” the name was changed because a village in Racine County already had this name. Sheboygan Falls is known for its rivers, as the Mullet and Onion Rivers join the Sheboygan River there. A dam once supplied hydroelectric energy to the area. Today, rapids and waterfalls provide a scenic backdrop, as do 40 historic buildings restored to their original late1800s appearance.

Back at the Old Plank Road Trail’s junction with Wisconsin State Highway 32, the route continues east past fields and small forests. As the path parallels Wisconsin State Highway 23, it descends. The trail crosses Rangeline and Woodline Roads before arriving at Highland Drive. It’s 2 miles from Wisconsin State Highway 32 to Highland Drive. On the west side of the road along the trail is a rest area with park bench and drinking fountain.

Diverting from the trail, a narrow paved path heads south along Highland Drive into Kohler. The village is the home of Kohler Company, a manufacturer known for its plumbing products. It was created in 1873 by John Michael Kohler and Charles Silberzahn. In 1900, factory operations moved from Sheboygan to the area that became the village of Kohler.

The village was originally called “Riverside,” but the name changed when the company moved there. Incorporated in 1912, the village was built as a model company town. Many of the Kohler company homes built between 1917-1931 still remain, and about 95% are now owner occupied. To preserve the historical aesthetic, the Kohler Company continues to retain final authority over the design of homes, business additions, outbuildings, and fences.

Today the village remain a quaint small town and manufacturing community. It also caters to tourists. The Kohler Design Center, American Club, and Blackwolf Run Golf Course are a few of the attractions visited by sightseers. Popular restaurants include the Immigrant Restaurant, the Wisconsin Room, and the Horse & Plow.

Returning to the Old Plank Road Trail after it crosses Highland Drive, the path journeys by the Hebrew Cemetery. It’s less than a mile to a tunnel under Interstate Highway 43. At the tunnel entrance, a spur trail leads south to a roundabout on Erie Avenue. The main trail travels through the lighted, 250-foot tunnel under the highway to arrive at the trail’s end. The trailhead here is basic, with a parking lot and nature trail.

The trailhead is at the end of Erie Avenue in Sheboygan. To reach it by car from Wisconsin State Highway 23 in Sheboygan, turn south on Taylor Drive. Go 0.2 mile and turn right (west) on Erie Avenue. Drive 0.6 mile to the end of the road and entrance to the parking lot.

The area that later became Sheboygan was originally the home of the Potawatomi, Ottawa, Ho-Chunk, and Menominee tribes. In Menominee, this place is known as Sāpīwǣhekaneh, meaning “at a hearing distance in the woods.” White Americans and European immigrants began arriving in the mid-1830s, after Native Americans ceded the land to the United States.

Sheboygan was incorporated in 1846. Over the next decade, a wave of German immigration swelled the population. The area was known for its lumbering, farming, and fishing industries. With its strong Germanic background, today Sheboygan is known as the “Bratwurst Capital of the World.” Additionally, the surfing crowd claims the city as the “Malibu of the Midwest” due to its freshwater surfing scene.

There are numerous attractions in Sheboygan, and plenty of places to eat. Der Sheboygan Biergarten at Kiwanis Park is open during the summer, serving steins of German beers with large soft pretzels. Live music is often featured there. Another place to savor a delicious brew is 3 Sheeps Brewing Company, which has an eclectic offering of ales, stouts, and lagers. Their taproom has become a popular destination in Sheboygan. Sheboygan’s bakeries are also renowned, including City Bakery, West Side Bakery, and Johnston’s Bakery.

^{Map of trailheads and addresses along this section of the trail.}

To experience the “Bratwurst Capital of the World,” visitors stop at Meisfeld’s to purchase award-winning bratwurst and other meats. Meisfeld’s has been in business since 1941, and offers 25 varieties of bratwursts. Trail-goers seeking something sweeter may enjoy South Pier Parlor, which has ice cream, malts, shakes, and fudge in a traditional-looking ice cream parlor right on the water. Whatever the craving, Sheboygan has plenty of dining options.

Trail last ridden and documented in May, 2024.