1. Oak Leaf Trail
The Oak Leaf Trail is massive - 116 miles, to be exact - and is one of the most extensive trail systems in the county. While you definitely couldn’t do it all in one go (unless you are really tough… and maybe a little crazy), this is an awesome trail to conquer in segments.
Most of the trail is paved asphalt, so it’s accessible for wheelchairs and strollers, but there are definitely a few hilly sections in the city. One of the most popular (and most beautiful) sections of this trail runs right along the stunning shore of Lake Michigan, offering amazing views from up on the bluffs and cliffside.
2. Hank Aaron State Trail
This 13.5 mile trail is a popular spot for walkers, runners, and cyclists… and it’s not hard to see why. It winds through some of the coolest parts of the city, following the Menomonee River from Lakeshore State Park, passing through the Historic Third Ward and right by Miller Park, before ending at Blue Mound Road in Elm Grove. Most of the trail is paved and easy to travel, but there are a few sections in the western section that are crushed gravel. There are several interpretive stops along the way that provide interesting information about the natural and cultural history of the area and the trail also connects with the Oak Leaf Trail for those looking to extend their adventure.
trail map and guide
for the Hank Aaron State Trail.
3. Milwaukee Lakefront
The Milwaukee Lakefront is definitely a favorite; its 5.9 mile loop has some of the best views of Lake Michigan in the city and is great for all skill levels. It’s a popular spot for road bikers, but the pathways are wide to keep traffic from getting too crowded. Whether you run or ride, this is one of the most beautiful spots in Milwaukee!
4. Havenwoods State Forest Trails
Havenwoods State Forest is a popular spot and is accessible year-round! There are several options for hiking here, most of which are rated easy and have little elevation gain from start to finish. It’s a cool little getaway, as you are surrounded by beautiful woodlands and wildflowers, which provide excellent opportunities for birdwatching. If you want to bring your furry friends along, there is a 2.5-mile Pet Trail where you can walk dogs on-leash. If you are into geocaching (or want to get started), the Trek Through Time Trail is a fun little adventure through the forest. You can pick up a guidebook at the Nature Center to get you started!
Wikimedia / PhotoGraphicBug
for Havenwoods State Park.
5. Ice Age National Scenic Trail - Holy Hill Segment
While the whole trail stretches more than 1,200 miles across the entire state, there are awesome spots to hop in for a quick hike! The trail is named for the location, which was the site of a terminal moraine during the Ice Age. The Holy Hill section in Hartford is about 6.8 miles long and leads up to a beautiful Basilica, where you can head up the spires for some incredible panoramic views of the surrounding area. During warmer seasons, the trail is lined with beautiful wildflowers that blanket the forested areas. It’s an easy trail, so it’s good for all ages and skills... and dogs can use this trail, too!
6. Greenfield Park Trail
This easy 1.2 mile loop is more of a walk than a hike, but it has some great lake views and is definitely kid-friendly. Greenfield Park is a beautiful little spot, filled with opportunities to see wildlife and birds as you wander around the small lake. There are tons of picnic areas here, so pack a lunch and go for a stroll!
7. Kohler-Andrae State Park
This scenic park sits right on the shore of Lake Michigan near Sheboygan and offers tons of activities to enjoy. There are several great, short trails here (many of them are open as cross country ski trails in the winter as well), including the Woodland Dunes Nature Trail (one mile, easy, and wheelchair accessible), The Dunes Cordwalk (two miles, moderately difficult), and Black River Trail (2.5 miles, also open to bikers and horseback rides).
for Kohler-Andrae State Park.
8. Parnell Tower Loop
Kettle Moraine State Forest - Northern Unit has more than 132 miles of trails to explore! The Parnell Tower Loop Trail is one of many awesome spots; it’s 3.5 miles long and leads uphill to the tallest point in the area, where you’ll find an observation tower that offers an incredible bird’s-eye-view of the surrounding natural area.
The view looking down from the 60-foot-tall tower is pretty dazzling as well!
for the Parnell Tower Loop Trail in Kettle Moraine State Forest - Northern Unit.
9. Tamarack Loop
This two-mile-long trail in Kettle Moraine State Forest - Northern Unit is an easygoing nature trail that loops around Mauthe Lake. You can access the trail via the State Forest Headquarters off of County Highway G or from the Entrance Station to the campground area on the southern side of the lake.
for the Tamarack Loop Trail in Kettle Moraine State Forest - Northern Unit.
10. Scuppernong Trails
This section of the Kettle Moraine - Southern Unit has three awesome loop trails that wind through stunning hardwood and pine forests. The shortest, the Red Loop, is 2.3 miles long and moderately difficult with several steep sections. The Green Loop (4.9 miles) is the most difficult trail, takes you through the beautiful forests on a roller coaster-like trail that passes by the Pinewoods Campground. If you aren’t up for a tough trail hike, head over to the Observation Loop. You can sit back, relax, and enjoy some beautiful lake views!
for the Scuppernong Trails in Kettle Moraine State Forest - Southern Unit.