Winthrop Harbor's Northern Gateway to the Lake County Bike Network
The Robert McClory Bike Path runs the length of eastern Lake County, roughly 25 miles of mostly flat, straight, tree-lined trail connecting a string of north shore communities from the Cook County line all the way to the Wisconsin border. And that border — the northern end of the entire trail — is right here in Winthrop Harbor. That makes the village the gateway between Illinois's north shore trail system and Wisconsin's, and a natural launch point for a ride of almost any length. Best of all, the long-rough northern section through the village was newly paved in 2025, giving riders a smooth, modern surface from Winthrop Harbor south.
About the Trail
The McClory path follows the bed of the old Chicago, North Shore and Milwaukee Railroad — the North Shore Line — whose rails were removed and paved over in the mid-2000s. The trail was named in 1997 for Congressman Robert McClory, who represented the area for 20 years and was an avid cyclist and jogger along this very corridor. It runs north and south through Winthrop Harbor, Zion, Beach Park, Waukegan, North Chicago, Lake Bluff, Lake Forest, Fort Sheridan, Highwood, and Highland Park, passing parks, forest preserves, community gardens, and Metra stations along the way.
For years the knock on the trail was its surface — asphalt in the south but crushed limestone through the northern communities. That changed in 2025, when Lake County completed a major paving project that laid asphalt across the gravel sections from Winthrop Harbor south through Zion, Beach Park, Waukegan, and North Chicago, along with road crossing and ADA upgrades. Some corridor enhancement work may continue, so it is worth checking the county's project page for current status before a long ride.
Riding from Winthrop Harbor
The trail's northern terminus sits at Russell Road in Winthrop Harbor, just east of Willow Hollow Lane at the Illinois and Wisconsin state line. From there you have two great directions to go.
- ·Head north: The McClory path connects directly to the Kenosha County Bike Trail, which continues about 3.5 miles to Anderson Park on the south side of Kenosha — a smooth, shaded, well-kept Wisconsin segment.
- ·Head south: You can ride as far as your legs will take you, through Zion and Beach Park toward Waukegan and beyond, with the option to turn a long ride into a loop or a one-way trip using the Metra Union Pacific North line that parallels the trail.
A Well-Connected Trail
One of the McClory path's best features is how it ties into the larger regional network. At its north end it meets the Kenosha County Bike Trail. At its south end it connects to the Green Bay Trail, extending the route deep into the northern Chicago suburbs. In Lake Bluff it intersects the East-West North Shore Bike Path, and it overlaps both U.S. Bicycle Route 37 and the Grand Illinois Trail. Because it runs alongside the Metra UP-N line — with stations at points including Lake Bluff, Lake Forest, and Great Lakes — riders can take the train one way and ride back, making almost any distance possible.
Who It Is For
The trail is flat, straight, and generally easy, which makes it well suited to families, casual riders, runners, and walkers, as well as long-distance cyclists looking to link up the regional network. It is also a popular birding route, especially in the open, park-lined stretches north of Waukegan. The best riding season runs roughly March through October. Leashed dogs are welcome.
Make a Day of It in the Harbor
Winthrop Harbor is the perfect base for a trail day. Start or finish at North Point Marina, which offers ample parking, restrooms, food at The Tropics and Harbor Brewing, and bike rentals if you did not bring your own. From the marina you are minutes from the trailhead at Russell Road, the beaches and trails of Illinois Beach State Park, and the birding at Spring Bluff Forest Preserve. Ride north into Kenosha for lunch, roll back to the marina, and finish with a drink overlooking Lake Michigan.
Video credit: YouTube — youtu.be/rdK04PScmD4
Whether you are out for an easy family ride, a long cross-county tour, or a quick spin across the state line for lunch in Kenosha, the Robert McClory Trail starts right here. Park in the Harbor, hit the path, and discover Lake County by bike.