Oak Leaf Trail Milwaukee

Wisconsin, Wilmaukee, Oak Leaf Trail


The Oak Leaf Trail is a 120-mile long trail meanders in and around the city of Milwaukee. About a quarter of the trail hugs the beautiful shores of the Lake Michigan. This trail is recognized as a jewel in the crown of Milwaukee County’s extensive trail system.



The trail is on a changing terrain of flat rural plains and hilly city streets. The trail is mostly smooth asphalt, with dozens of easily accessed connections that take you just about anywhere in the Milwaukee metro area.



The Oak Leaf Trail has several access points in and around the Milwaukee metro area. A recommended starting point is the Milwaukee Art Museum, where 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. There is a trailhead parking lot at the Milwaukee Art Museum.

Otherwise, to reach the trailhead at Dretzka Park Golf Course (and the northwesternmost segment) from I-41 in Menomonee Falls, you can take Exit 50A for SR 100 East / Main Street Merge onto Main Street heading east, and go 0.8 mile. Then take a right turn (south) onto Old Orchard Road, go 0.8 mile. Turn right onto North 124th Street, and go 0.1 mile. Turn left, pass Dretzka Park Disc Golf to your left, and finally turn left into the golf-course parking lot.

Another trailhead can be reached is the southwestern trailhead at the Milwaukee County Sports Complex Fieldhouse, where you can access 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.


More details

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. South of downtown, there is an old warehouse district that has been converted into lofts and condos. In the next few miles, the trail will carry you down to magnificent Lake Michigan and its beaches. Several kiosks advertise refreshments, and ample parking and restrooms are available.

In 2015, the Oak Leaf Trail was extended near the northern end of Estabrook Park, home of a popular beer garden, in Whitefish Bay. If you head north from here, you’ 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. Traffic on this trail is said to be pretty light and polite.

You may see one or two coyotes in the more remote areas, particularly at dusk. Maintain your distance as they are wild animals, though coyotes are quite common here. Good way to scare them away is to talk loudly. You can also spot many species of birds along the trail.

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122.241 km / 75.957 mi

Total Distance

400 m / 1,312 ft

Total Ascent

378 m / 1,241 ft

Total Descent

240 m / 786 ft

Highest Point

Ride type:
Mountain biking
Road riding
Rail Trail
Difficulty: Intermediate (Red)
Ride Duration: options
Fitness Level: Medium
Shared Bike Path - Paved
Shared Bike Path - Dirt
On-Road Bike Lane
Off-Road - Fire Trail
Off-Road - Rail Trail
Off-Road - Single Track
Off-Road - Downhill
Gravel Road
Trail Signage: Good
Mobile Coverage: Limited
First Aid
Bike hire
Bike servicing
Accessible by bike
Accessible by car
Accessible by public transport
Accessible by shuttle
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