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The Oak Leaf Trail is the jewel in the crown of Milwaukee County’s extensive trail system. The trail meanders for more than 125 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 secondhand 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 access points in and around the Milwaukee metro area. The best starting point is the Milwaukee Art Museum, after which you can head either north or south along Lake Michigan, or just a short distance south and west to an additional set of inland trail segments.
In the more remote areas, particularly at dusk, you may spot a coyote or two. Coyotes are common but are wild animals, so maintain your distance and keep your pets close and on a leash. Talking loudly will easily scare coyotes away.
Many species of birds can be found along the trail as well, and 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, after which the trail carries you down to magnificent Lake Michigan and its beaches. Several kiosks advertise refreshments, and you will find ample parking and restrooms.
In 2015, the Oak Leaf Trail was extended near the northern end of Estabrook Park, home of a popular beer garden, in Whitefish Bay. Heading north from here, you’ll traverse elevated grade over I-43 into Glendale and Brown Deer, passing alongside Brown Deer Park to W. Brown Deer Road. Here, you’ll connect seamlessly with another section of the Oak Leaf, which then connects with the Ozaukee Interurban Trail, a 30-mile pathway to Cedar Grove.
Additional or nearby connections made by the Oak Leaf Trail include the City of Franklin Hike and Bike Trail, MRK Trail, Forked Aster Hiking Trail System, Wehr Nature Center trail system, Milwaukee Urban Water Trail, Hank Aaron State Trail, Lake Michigan State Water Trail, City of Milwaukee Beerline Trail and Kinnickinnic River Trail, West Allis Cross Town Connector Trail, and numerous mountain biking trails, including Alpha, Bubba’s Woods, Hoyt, and Oak Hill.
The extension of the South Shore Line trail segment is open all the way to Bender Park, but the surface is currently made up of 1-inch sized crushed stone. Typically used as a base layer under asphalt pavement, it is very difficult to ride on, even with a gravel or other rough-terrain bike. Development plans for the trail include paving this segment with asphalt in 2023. Trail signage has been placed along the route and a new creek bridge for pedestrians/bicyclists has also been built.
To reach parking at the Milwaukee Art Museum from I-43, take Exit 72B east toward Lakefront. After 0.8 mile, merge onto I-794 E., and go 0.3 mile. Keep right to stay on I-794 E. another 0.2 mile, and take the exit on the left toward N. Lincoln Memorial Dr. Go 0.3 mile, and turn left onto N. Lincoln Memorial Dr. Go 0.2 mile, and turn right onto E. Michigan St. After 0.1 mile, turn left into the trailhead parking lot.
To reach the trailhead at Dretzka Park Golf Course (and the northwestern-most segment) from I-41 in Menomonee Falls, take Exit 50A for SR 100 E./Main St. Merge onto Main St. heading east, and go 0.8 mile. Turn right (south) onto Old Orchard Road, and go 0.8 mile. Turn right onto N. 124th St., and go 0.1 mile. Turn left, pass Dretzka Park Disc Golf to your left, and turn left into the golf-course parking lot.
To reach the southwestern trailhead at the Milwaukee County Sports Complex Fieldhouse from the intersection of WI 100/W. Ryan Road and S. 60th St. in Franklin, head north on S. 60th St. for 0.5 mile. Parking is available to your right in the complex parking lot.
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