The Oak Leaf Trail is the jewel in the crown of Milwaukee County's extensive trail system. The trail meanders more than 115 miles in and around the city of Milwaukee on a changing terrain of flat rural plains and hilly city streets. Nearly a quarter of the trail hugs the beautiful shores of Lake Michigan.
The trail is mostly smooth asphalt, with dozens of easily accessed connections that take you just about anywhere in the Milwaukee Metro Area. Three miles of the trail follow the route of an old Chicago and North Western line that was part of the railroad company's long-distance passenger service to Denver, Colorado and the California coast. The railroad's penchant for purchasing much of its equipment second-hand earned it the nickname "The Cheap and Nothing Wasted." The balance of the trail is made up of parkways and city streets, as well as another 3 miles open on a former Union Pacific corridor.
The Oak Leaf Trail has more than 22 access points in and around the Milwaukee Metro Area. In the more remote areas, particularly at dusk, you may spot a coyote or two. Coyotes are common but are wild animals, so keep your distance and keep your pets close and on a leash. Talking loudly will easily scare coyotes away.
Many species of bird can be found along the trail as well, and bird watching is enough of a pastime here that Milwaukee County Parks has developed bird trail maps directing you to prime spotting locations.
Near mile 10, hilly city streets wind through an eclectic mix of Milwaukee's middle and upper-middle class neighborhoods. You will pass three golf courses in short succession. Just south of downtown there is an old warehouse district that has been converted into lofts and condos. Then the trail carries you down to magnificent Lake Michigan and its beaches.
You'll cover a lot of ground along the trail, which adds up to a great ride. Several kiosks advertise refreshments, and you will find ample parking and restrooms.
The best starting point is at the Milwaukee Art Museum, then traveling either north or south on the trail from here. Whether logging just a few miles or canvassing the entire route, this is one trail you are sure to enjoy.
From points north, west and south (I-94 and I-43), take I-794 east and Exit 1E toward N. Van Buren Street; turn left on N. Van Buren then right at E. Michigan Street. Follow E. Michigan to the end. From there you will begin to see the Lake Michigan waterfront. The Milwaukee Art Museum/Information Center will be on the left side of the parking area.