10 Best Hiking Trails in Milwaukee, Wisconsin


Milwaukee Wisconsin has amazing hiking trails!

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Experiencing nature and the benefits of a good hike does not take extensive planning or even traveling far out of Milwaukee. This article rates the best hikes in, or around Milwaukee, Wisconsin you need to experience for yourself!

Caleb and I try to get on a hike with the doggies as often as possible. These hikes are great at any time of the year and some harder than others. Milwaukee, Wisconsin has a variety of hiking trails with different views, lengths, and levels of difficulty. 

kohler andrae park
The Cord Walk at Kohler Andrae

10 Best Hiking Trails in Milwaukee, Wisconsin

1. Oak Leaf Trail

The 116-mile trail circles around the city of Milwaukee, offering something for all levels of adventures! The Oak Leaf Trail has many paved paths for leisurely strolls accessible by wheelchairs, strollers, and bicycles. Trails will elevation leads to more advanced parts of the Oak Leaf Trail and lead to breathtaking views. A section of the trail even runs along a cliffside overlooking Lake Michigan. Oak Leaf Trail is an overall convenient and lovely path for everyone to enjoy. 

2. Parnell Tower Loop, Kettle Moraine State Forest 

Located in the Kettle Moraine State Forest, about 40 miles from the city of Milwaukee, is a 3.5-mile hike to incredible views. If the views from the trail are not enough for you, there is a 60-foot-tall tower along the path to giving you an even better view above the trees. The Kettle Moraine State Forest is home to 132 miles of trails to venture. While you are in the area make sure to check out Lapham Peak, Tamarack Loop, and Scuppernong Trails which also lends themselves to wonderful hiking experiences. 

hiking trails close to milwa

3. Hank Aaron State Trail

The Hank Aaron State Trail is a great opportunity to experience the history of Milwaukee, popular scenery, and enjoyable physical activity. The trail was named in honor of Milwaukee’s famous baseball player Hank Aaron, which is fitting as part of the trail passes by Miller Park and ends at Blue Mound Road in Elm Grove. Many more beautiful views can be seen along the 13.5-mile trail. Some of the trails even travel along Lake Michigan. Wheelchairs, strollers, walkers, runners, cyclists, and canine friends all are welcome on this popular Milwaukee trail. 

4. Milwaukee Lakefront Trail 

Milwaukee hikers find out quickly how the Milwaukee Lakefront Trail gets its name. This 5.9-mile lakefront loop has incredible views of Lake Michigan from the city.  The trail is well maintained and wide enough for many quests to experience these views. 

Caleb and Ren

5. Trek Through Time Trail, Havenwoods State Forest Trails

Located in the Milwaukee city limits, Havenwoods State Forest is a way to escape the hustle and bustle of everyday life for a relaxing hike through the woods. This park is open all year round. The 6 miles of trails (mostly paved) wind through scenes of wildflowers, woods, and wildlife. Visit the Trek Through Time Trail for geocaching fun, which is enjoyable for all ages.  

6. Ice Age National Scenic Trail – Holy Hill Segment

The Ice Age trail stretches more than 1,200 miles across the entire state, which an overwhelming number of breathtaking trails and views. The segment we recommend is the beautiful Holy Hill Segment as a hike for all skill levels and their pups too. The Holy Hill section in Hartford is a 6.8-mile trail through a lush forest area, highlighted with wildflowers in the spring and summer. 

7. Greenfield Park Trail

Great for picnics, day trips, or even extensive hikes, the Greenfield Park Trail is a destination for all. Just outside the city, Greenfield Park Trail is a 1.2-mile paved loop featuring a lake with opportunities to see wildlife along your walk.  Bring along your family, friends, and or puppy pal for a beautiful day on this trail. 

8. Lion’s Den Trail

Located about 20 miles outside of Milwaukee is a 3-mile loop of hills and cliffs which makes up the Lion’s Den trail. The highlight of this trail is the stunning views of Lake Michigan that are offered along the way. For those who normally hike with a stroller, be warned that there are some stairs on this trail. Dogs are welcome to accompany their owners.

9. Seven Bridges Trail: Grant Park

This is one of my favorite hikes in Milwaukee, Wisconsin! I love taking the dogs to the beach and letting them run with a long lead!

Psst: I also love this park because it is the perfect location for your Wisconsin Family Portraits! Did you know I am rated one of Wisconsin’s Best Family Photographers?

South Milwaukee houses the 2 mile Seven Bridges Trail, which is just as it sounds, a trail through seven bridges.

This trail, however, has so much more to offer. The trail has a reputation of being haunted, but don’t let that scare you away. There are many interesting structures along the trail to capture with your camera. The Seven Bridges Trail comes to an end by opening to Lake Michigan beachfront. Not a bad way to end a haunted hiking trail. Grant Park is beautiful any time of the year, but Fall is my favorite. Hiker’s come from all over to view the incredible fall foliage. 


10. The Black Marsh Boardwalk, Kohler-Andrae State Park

The Black Marsh Boardwalk trail is only 1/4  of a mile but it offers great views all year round. This short but sweet hike really shines when the marsh is flooded. The boardwalk floats above the water for an amazing experience. The state park includes other impressive hikes like The Dunes Cordwalk, Woodland Dunes Nature Trail, and Black River Trail. Many of the trails in Kohler-Andrea State park, such as The Black Marsh Boardwalk is wheelchair/stroller accessible and dog friendly (but they must be on a leash). Caleb and I walked this trail last year with Kenzo & had a picnic lunch on the beach for our one-year wedding anniversary!

kohler andrae park


Did you know Wisconsin has hiked with waterfalls? Neither did I! But after some research, I’ve rounded up 7 Wisconsin Hikes with Waterfalls!


Happy Hiking!

What are some of your favorite hikes near Milwaukee, Wisconsin? Join me on Instagram @House_Fur and strike up a conversation! 

10 milwaukee Wisconsin hiking trails

Join the Conversation

  1. Great post. I’ve only tried number 1 and 7 trail. And they are awesome. Thanks for giving the list. I’ll definitely try the other trails on our next hiking activity.

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