Pine Line Trail: Westboro to Medford
In northwestern Wisconsin, the section of the Pine Line Trail traveling south from Westboro to Medford offers beatiful views of the rural countryside. The 15.2-mile path journeys from the Wisconsin north-woods into farmland, passing hardwood and conifer forests, as well as low marshlands near the Black River and its tributaries.
This section of the trail varies in elevation. While it generally moves downhill from Westboro to Medford, there are several long gradual inclines and declines. In Taylor County, the surface is crushed granite, where bicycle tires 32mm or wider work best. In the final 5 miles north of Medford, the surface is screened limestone.
The Pine Line Trail is open to horseback riding, with signs directing riders to travel on the grassy edges of the trail. This suggestion doesn’t appear to be followed always, as hoof marks and ruts were found throughout the graded path at the time this trail was ridden. ATVs are also seen using the trail, despite signs prohibiting these motorized vehicles on the path.
The Pine Line Trail’s trailhead in Westboro is at the corner of County Highway D and Old State Highway 13. It’s a modest trailhead, with parking lot and gazebo. To access the trailhead by car from Wisconsin Highway 13, turn east on County Highway D (North Street) in Westboro. Drive 0.3 mile and turn right (south). The parking lot is 450 feet down the road.
Westboro was created as a township in 1847, and a community developed decades later on the Wisconsin Central Railroad line. Westboro was named after the town in Massachusetts.
From Westboro, the Pine Line Trail heads south. After a short distance, a marker indicates the site of the community’s old railroad depot. About 350 yards down the path, it crosses Silver Creek over a high bridge. The view to the east is beautiful. Less than a half mile further, the trail crosses Fisher Creek and runs next to it under Wisconsin State Highway 13. Now on the west side of the highway, the trail crosses Fisher Creek again, and a third time 0.4 mile down the path.
From Wisconsin State Highway 13, it is 1.4 miles to Gunnar Road. The landscape reveals a mix of hardwood and conifer forest, and low marshland. After Gunnar Road, more farm fields appear. In early autumn, circular hay bales fill the fields and provide scenic views.
A mile south of Gunnar Road, the Ice Age National Scenic Trail crosses the trail. A half mile further, signs identify the route to Chelsea Lake County Park. A short spur trail leads west to Chelsea Lake Lane. From the trail, it is only 0.3 miles to this well-equipped park with restrooms, parking lot, boat landing and dock, picnic tables, and grills.
By car, Chelsea Lake County Park is accessed from Wisconsin State Highway 13 by heading west on North Street. Continue straight on N. Chelsea Avenue to Fisher Creek Road. Turn right (north) and drive 0.5 mile. Turn left (west) on Chelsea Lake Lane and drive 0.3 mile.
Before reaching Chelsea, the trail crosses the Black River. At this point it’s just a small stream flowing south, sometimes next to the trail. The path crosses several of its tributaries along the way. In Medford, the trail crosses the river again.
After crossing Chelsea Avenue, the trail runs through Chelsea. There, a marker indicates the town’s historic train depot location. Chelsea was named by the president of the Wisconsin Central Railroad Company for a town of that name in Massachusetts. It was settled in 1874. In addition to being a railroad town, it had a successful mill that made shingles.
From Chelsea to the Whittlesey Lions Park, the path runs for 5.5 miles by forests, wetlands, and fields. Ginseng fields appear along one short section of the trail. Easily identified, they’re covered with a characteristic black tarp raised by six-foot poles. Wisconsin produces high-quality ginseng, which is used both in cooking and natural healthcare.
The Pine Line Trail passes through Whittlesey at Settlement Road. A sign reveals a historic depot site. Some believe the community was named for Charles Whittlesey, an officer at 19th century Fort Howard in Green Bay who later surveyed the area. Others think it was named for the first legislator of the district, Asaph Whittlesey. Another claim is that the railroad company named it from a Native American word meaning “sandbar.”
A half mile south of Settlement Road, the trail passes Whittlesey Lions Park. On the west side of the trail, a small campground has a portable toilet. On the east side of the trail are restrooms, parking lots, a picnic area, ball fields, and a playground. To reach the park by car, turn west on County Highway M from Wisconsin state Highway 13. Drive 0.3 mile to Ballpark Road. Turn right (north) and go 0.4 mile to the park entrance.
From Lions Park, it is 0.6 miles to County Highway M. A mile further the trail crosses Pleasant Avenue. The final 3-mile section runs from Pleasant Avenue to Allman Street. Running near the Black River, park benches overlook the small stream. The Pine Line Trail technically ends at Allman Street, where a parking lot and information kiosk are located.
Trail-goers may continue to Medford by taking the trail across Allman Street. It leads 350 yards through a forest. The path then divides. One route continues straight, passing through Veterans Memorial Park. In addition to the memorial, a parking lot, picnic tables, playground, and outdoor exercise equipment are found there.
Going to the right (west) takes cyclists over the Black River to Medford City Park. Located on the west side of the river, this park has an outdoor swimming and wading pool, playground, outdoor exercise equipment, athletic courts and fields, concession stand, and skatepark. It also has shelters with picnic tables, restrooms, and walking trails along the river and millpond. A small riverside campground with nine campsites rounds out the amenities.
To reach the Medford City Park by car from Wisconsin State Highway 13, turn west onto Broadway Avenue in Medford, and drive 0.8 mile. After crossing the Black River, turn right (north) on Luepke Way. The road becomes Centennial Parkway, and the park begins there and extends a half mile northward.
The Ojibwe people once lived on this land, which the U.S. government acquired in 1837. In 1864, the federal government authorized a land grant to subsidize railway construction in the area. The Wisconsin Central Railroad Company obtained the grant and constructed a line in the 1870s. The railroad company and a local lumber company laid out the city of Medford in 1875, naming it after Medford, Massachusetts.
Map of trailheads and addresses along this section of the trail.
Today, Medford is the seat of government for Taylor County. It has several hotel accommodations and restaurants to meet the needs of visiting trail-goers. For a smaller-sized city, its 100-acre city park is quite extensive and offers an abundance of amenities.
Trail last ridden and documented in September, 2022.