12 Reasons to Visit the Oak Leaf Trail

12 Reasons to Visit the Oak Leaf Trail

It’s always a good day for a jaunt on one of Milwaukee’s greatest trails.

1) See the city

photo by Russel Tinsley

This trail roams and rambles for over 120 miles in and around Milwaukee. For the water lovers, just about a quarter of the trail overlooks the shores of Lake Michigan.

2) Hop on and off at major landmarks

Milwaukee Art Museum
Photo by Meghan Quadracci

If you are tired from your jog, walk or all that greenery, the trail can lead you out and into the Milwaukee metro area. Stops include the Milwaukee Art Museum, the Urban Ecology Center, Dretzka Park Golf Course, Milwaukee County Sports Complex Fieldhouse and Bradford Beach.

3) Commune with nature


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During the day, you’ll see many species of birds from the trail. Bird trail maps can direct you to prime spotting locations. But at night, be aware of wild coyotes. Being loud can scare them away.

4) Expand your exercise horizons

photo courtesy of Visit Milwaukee

The trail routinely plays host to runners, bikers and dog-walkers alike. But you can also strap on a pair of rollerblades, take a skateboard or scooter, or just enjoy a leisurely walk.

5) Connect with other trails

Beerline trail
Photo by Dominic Inouye

The Oak Leaf Trail connects to many other trails including the Hank Aaron State Trail, the Beerline Trail and the New Berlin Recreational Trail. Use the Lake Loop to start your day perusing the Milwaukee Art Museum War Memorial and end at Veterans Park for a picnic. Or take the South Shore Line to visit Bay View from Downtown. Hop from the Hank Aaron to the Oak Leaf to get between the city and the west suburbs

6) It’s incredibly picturesque

photo via Visit Milwaukee

The whole trail makes a great photo op. Enjoy the changing leaves in the fall, snow-covered twigs in the winter or thick greenery in warmer weather. The Oak Leaf Trail is a breathtakingly beautiful site any time of year. 

7) You can enjoy it year round

Milwaukee's Veterans Park in the snow
Milwaukee’s Veterans Park in the snow

Lucky for you cyclists, 85 percent of the trail is kept clear during our sometimes-nasty winters. The trail is diligently plowed within 48 hours of a snowfall.

8) Stop for a cold one

Estabrook Park Beer Garden
Estabrook Park Beer Garden

Need an ice cold beer stop along the way? Estabrook Park’s beer garden is conveniently situated between the trail and the Milwaukee river, making it accessible by foot, bike, kayak or car. Hubbard Park Beer Garden is another good option, also along the Milwaukee River Line.

9) Commute to work


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The Oak Leak Trail is a great way to get around the city for those eschewing car travel. Chances are, if you live and work Downtown, you can reroute at least part of your commute to the trail, where there’s no threat of car traffic.

10) Take a breather


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Allow the sound of serenity and nature views to take you out of the city life for a few moments of me-time. Taking time for a breath of fresh air is often necessary in a busy city like Milwaukee.

11) Go for the dogsDogs making friends at Bastille Days

The Oak Leaf Trail is one of the few public places that allows dogs. Your pet will be happy you brought them, and so will you; just make sure they are on a leash. Don’t have a dog? Enjoy the one’s you pass as you traverse the trail.

12) Stop for a bite

Breaking bread at Simple Cafe’s bar; Photo by Adam Ryan Morris

If your stomach starts to growl halfway through your workout, stop at one of the many eateries lining the trail. Might we suggest Simple Café on Farwell? Their patio lies on the North side of the building, with a path through which bicyclists can enter and exit. There’s also Colectivo on the Lake, or anything on this list of restaurants near the Oak Leaf Trail from Trip Advisor.