8 of the Best Running Routes in Milwaukee

Here are some of the best spots for a jaunt through Milwaukee.

Sometimes there’s nothing better than the feeling of your feet pounding against the pavement, your legs pumping, your chest heaving with each breath as you run through the streets. I can’t imagine when that would actually be, but I have to imagine for someone somewhere that is sometimes the case. For many of us, running is a necessary part of fighting the hopeless battle against slowing metabolism, for others its a endorphin-producing pleasure. Whatever your motivation, here are some of the best spots for a jaunt through Milwaukee.

1-2 miles

Milwaukee Riverwalk (Urban)

Starting at Clybourn St., you can run alongside the Milwaukee River northward all the way to Humboldt Ave. for a roughly two mile run. It’s one of the only places you can run in the heart of the city without getting in everyone’s way and having to juke out passing cars like an NFL tailback. The only drawback is an occasional fish stench rising up from the mysterious waters, but otherwise this is a top-notch quick run. 

Washington Park Urban Ecology Center (Urban/Nature)

If you’re looking to hit a quick mile without getting too far out of the city, haul yourself over to Washington Park. They have a big old pond outside of the Urban Ecology Center that provides a centerpiece for your run. The park is larger than just the pond, which makes this a malleable trail, if you feel like pushing yourself a bit and run another mile (maybe “Eye of the Tiger” just came on your headphones).

3 miles/5 kilometers

Oak Leaf Trail (Lakefront)

Oak Leaf Trail is a massive city-wide trail with a vast and fascinating ecological history sure to fascinate the urban-planning lover in all of this. But this article is about running, so forget all that history. For this 5k, start the trail at Veterans Park and run northward along the lake-shore, past Bradford Beach, all the way to Lake Park and the North Point Lighthouse. You’ll get in a scenic run that would make Zip Morgan proud.

Hoyt Park (Nature)

Surprise surprise, the Oak Leaf Trail strikes again—this time in Wauwatosa. This 5k gets you a little bit out of the city and into Hoyt Park, alongside the Menomonee River. The Oak Leaf Trail continues its massive loop through this forested park, which provides a shady, pleasant place for a short or long run, depending on your mood.

5-6 miles

Hank Aaron State Trail (Urban, Lakefront, and Nature)

A trail that pays tribute to the great Brewer and loops around a Lakeshore inlet, down through the city and through wooded areas. It’s a multi-faceted city trail that’ll get you a heart-pumping mid-distance run with enough visual variety to keep you entertained.

Grant Park to Sheridan Park (Lakefront)

Man, Oak Leaf Trail really dominates this city. You even head southward to St. Francis, and you still run into the Oak Leaf Trail. This time the trail cuts through grant park right along the lake all the way up to Milwaukee. You can cut off at Sheridan Park for a roughly 5-6 mile run or keep going as long as you want.

Over 10 Miles

Bugline Trail (Urban/Nature)

Waukesha—what a place. It has all the wauks. It has all the eshas. It has it all, including a nice trail that runs woods, glens, and huge quarries. This is a big and scenic route that will provide all you need for your long run. The total trail about 16 miles long, so you can easily work in a half-marathon or double it back and go for the full-shebang.

Kettle Moraine State Forest (Nature)

The Lapham Peak Unit of Kettle Moraine offers a wide variety of potential trails, which loop into each other and allow for a long journey through the wilderness. Ascend your way up to the peak, down and around and all around, and soon enough you’ll have run a full marathon.



Archer is the managing editor at Milwaukee Magazine. Some say he is a great warrior and prophet, a man of boundless sight in a world gone blind, a denizen of truth and goodness, a beacon of hope shining bright in this dark world. Others say he smells like cheese.