There’s no need for a car to enjoy some of the best spots in Wisconsin’s largest city. If you’re a biker, hiker, runner, or walker you can explore the heart of Milwaukee via the Oak Leaf Trail, a 135-mile pedestrian route that encircles the city. It’s popular with both locals and visitors alike, and because it’s so long, you’ll find segments all over town. If you’ve spent any time in Milwaukee, you’ve probably encountered a stretch of the Oak Leaf. Here’s what you need to know about this incredible Wisconsin trail.

The trail has a very long history. It was first envisioned back in 1939 by bicycle advocate Harold "Zip" Morgan. The groundbreaking idea took a little while to gain traction – actual work on the parkway did not start until 1966.
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The trail will take you to the doorstep of many of the city’s attractions, including the Milwaukee Art Museum, Bradford Beach, and the Milwaukee County Sports Complex Fieldhouse.
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Today the Oak Leaf Trail is a sprawling system of inter-connected trails, including asphalt paths, parkways, and designated road sections with designated bike lanes and sidewalks. It connects the whole city with a “ribbon of green.”
Milwaukee County Parks

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The trail segments are well marked and include beautiful natural areas where you’ll see migratory birds like ducks and geese as well as urban stretches that will help you thread a bustling cityscape. About a quarter of the trail follows the edge of Lake Michigan.
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The trail also passes many city parks, including Veteran’s Park, Lake Park, Lincoln Park, Hoyt Park, and Estabrook Parkway.
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You’re never far from a great Milwaukee restaurant, pub, coffeehouse or cafe when you’re on the Oak Leaf Trail. The trail also passes some tranquil outdoor beer gardens and scenic lakeside rest spots.
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If you're looking for a scenic adventure in Milwaukee, this is it!
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There are scores of places to begin a walk or ride on the Oak Leaf Trail. The Milwaukee Art Museum is a good spot to start – from here you can head north or south along the lake. The trail also connects to many other trail systems, including the Hank Aaron Trail, the Kinnickinnic River Trail, and the Milwaukee Beerline Trail.

Once you’ve tackled trails in the Milwaukee area, here’s another Wisconsin trail that offers miles of gorgeous scenery and a few abandoned tunnels.

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Oak Leaf Trail, Milwaukee, WI, USA