The mainline Oak Leaf Trail runs from the Brown Deer trail in Brown Deer Park on the North Side to Lakeshore State Park downtown, where it meets The Hank Aaron State Trail. On the South side, the mainline Oak Leaf Trail meanders along Lake Michigan through parkways to Grant Park.
The trail is mostly smooth asphalt, with dozens of easily accessed connections that take you just about anywhere in the Milwaukee Metro Area, including its most spectacular parks. A good starting point is at the Milwaukee Art Museum, then traveling either north or south on the trail from there.
Our mapped route is nearly 5 miles one way, between the Milwaukee Art Museum in the south, and then along the water heading north, looping through Veteran’s Park, which is just east of the south end of the path. (Bonus: the park has a 20 station exercise course, so you can get in a little strength training while you’re at it!) The north end point is Olmsted’s Lake Park. From there, you can continue onto one of the many other portions of the trail (Oak Leaf Trail, Brown Deer Trail, Ozaukee Interurban Trail) or loop back to the Museum.
End Points: Range Line Rd. at Dean Rd. (River Hills N of Milwaukee) to S Howell/SR 38 (Root River Parkway nr. Caledonia).