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15 Best Southern Wisconsin Hiking Trails

Guide to the best places to hike in Southern Wisconsin for every level

Wisconsin is a paradise for nature lovers, full of fantastic hiking trails and beautiful places worth hiking to.

But the Southern Wisconsin hiking trails are undeniably some of the best in the whole state and some of my favorites!

So, if you’re looking for places to hike in Wisconsin, grab your hiking water bottles and vegan hiking boots and head to the southern half of the state.

I’ve hiked all over the state and fell in love with Southern Wisconsin’s hiking as it is full of diversity – from nature to skill level.

If you are headed to Southern Wisconsin and looking to explore more outdoors, these trails are the perfect place to start.

Wisconsin is a paradise for nature lovers as it is full of amazing hiking trails and beautiful places worth hiking to. But the Southern Wisconsin hiking trails are undeniably some of the best in the whole state, and some of my favorites! This guide has all the best places to hiking southern Wisconsin, including in Milwaukee, Madison, and hidden gems. #Wisconsin #SouthernWisconsin #Milwaukee #Madison #Hiking #HikingTrails #WisconsinHiking #WisconsinOutdoors #WisconsinTrails #Nature
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1. Seven Bridges Trail

Where: Milwaukee, WI

Length: 0.5 miles

Difficulty: Very Easy

hiking in Milwaukee, wooden bridge in the forest connecting the seven bridges hiking trail
Seven Bridges Trail

“Enter this wild wood and view the haunts of nature”, says the welcome message on the wooden archway at the entrance of Seven Bridges.

Hiking in Milwaukee, in wild nature, just a few minutes from the urban center?

Definitely one of the coolest things to do in Milwaukee, and one of the best outdoor activities in Milwaukee.

After a few minutes among the trees, I realized the description fits perfectly.

The design of the paths makes the park look larger than it is.

The ravine of a small brook flowing down to lake Michigan gives it a wilder look. The wooden bridges add a “Lord of the Rings” touch.

The forest reaches the beach below, which looks totally pristine as if you were far away from civilization.

This fairy-tale forest park has become one of my favorites among the best hiking trails in Wisconsin.

In addition to being one of the best Southeast Wisconsin hiking trails, Seven Bridges is one of the best spots to see fall colors in Wisconsin.

Thus making it one of the best things to do in Milwaukee in October!

However, hiking is one of my favorite things to do in Milwaukee year-round, and I even recommend it as one of the best things to do in Milwaukee in winter.

Seven Bridges Trail is great for a romantic day out, and one of my favorite date ideas in Milwaukee.

If you are visiting the city with your partner, consider making your stay extra special at one of the most romantic hotels in Milwaukee.

Seven Bridges is pet-friendly and suitable for all levels, making it great for the whole family to enjoy.

If you are visiting the area with pets, consider staying at one of the best pet-friendly hotels in Milwaukee.

Book here the best tours in Milwaukee

2. Kenosha Dunes Trail

Where: Kenosha, WI

Length: 2 miles

Difficulty: Easy

places to hike in southern Wisconsin, sandy path along the Kenosha Dunes Trail
Kenosha Dunes Trail

Natural sand dunes in a preserve that hosts up to 75 species of birds? Sign me up!

I heard about this little gem while I was looking for the best things to do in Kenosha.

The locals love to go to the dunes with their kids or to walk their dogs, because of the peaceful atmosphere and the beautiful views on Lake Michigan.

Just keep on walking after South Port Park, which is also nice for walking and biking and has one of the best beaches in Wisconsin.

The sand dunes formed 10.000 ago when the glaciers covering North America withdrew.

Despite being one of the shortest hiking trails Southeast Wisconsin offers, this is a unique environment.

While in Kenosha, be sure to walk past the shore and see the Kenosha North Pier Light, one of the best lighthouses in Wisconsin.

Book here the best cabins in Kenosha

3. Devil’s Doorway Loop

Where: Baraboo, Wisconsin Dells, WI

Length: 1.9 miles

Difficulty: Moderate

best hiking in Wisconsin Dells, natural rock formation overlooking lake
Devil’s Doorway Loop

The iconic Devil’s Doorway is a spectacular rock formation, a must-see when exploring southern Wisconsin hiking trails!

The reddish rock outcrop looks like a doorway, though it was not made by the devil but by a prehistoric glacier.

Reach this natural monument, and enjoy a spectacular view of Devil’s Lake by climbing up along the natural rock stairway, one of the best hiking in Wisconsin Dells.

Be careful if you are a beginner: the “stairs” are steep, some trail parts are exposed to sheer drops, and the rocks can be slippery.

Forget about sandals and put on some solid hiking boots!

The Devil’s Doorway is one of the best places to hike in southern Wisconsin, but you still need to use some precautions.

Once you have had your fill of hiking in nature, drive a little bit further north and discover a whole series of fun things to do in Wisconsin Dells.

Hiking this trail is one of the best things to do in Wisconsin Dells in winter – the park even has a winter campsite!

This is one of the best campsites in Wisconsin Dells and the surrounding area.

Book here the best tours in Wisconsin Dells

4. Lake Geneva Shore Path

Where: Lake Geneva, WI

Length: 22 miles

Difficulty: Moderate

hiking in southern wisconsin, paved path along the shoreline of Lake Geneva
Lake Geneva Shore Path

Lake Geneva is one of the best lakes in Wisconsin, but also has a few excellent spots for hiking in Southern Wisconsin.

In fact, hiking is part of what makes the romantic getaways in Lake Geneva so special.

My original plan was to hike a shorter trail in Big Foot Beach State Park, but when I got to the Lake Geneva Shore Path the first in a series of beautiful historic houses caught my eye.

So I continued.

Luckily I wasn’t disappointed, and walking the Shore Trail is one of the best things to do in Lake Geneva.

You will pass through private properties and behold an impressive showcase of the residential architecture of southern Wisconsin.

Thanks to this out-of-time atmosphere, Lake Geneva is high on my list of romantic getaways in Wisconsin.

In Fontana, I discovered The Abbey Resort, one of the most romantic hotels in Wisconsin and stayed for the night.

The following day, I hiked back via the Northern Shore trail.

If the weather is hot and you need a break, be sure to check out the Lake Geneva Clue Room, one of the best escape rooms in Wisconsin!

Lake Geneva has some of the best lake resorts in Wisconsin to relax and shower after a long day of hiking!

Plus, even if you visit Lake Geneva in winter, you’ll still be able to access the Shore Path and enjoy the crisp fresh air on your walk.

Book here the best tours in Lake Geneva

5. Holy Wisdom Nature Trail

Where: Madison, WI

Length: 2 miles (North Prairie Trail)

Difficulty: Very Easy

hiking in madison, Tenney Park bridge on a fall morning
Tenney Park bridge, Madison

When searching for the best hiking in Madison, WI, I stumbled upon a true hidden gem: Holy Wisdom Nature Trail.

Restored to its natural state by Benedictine nuns, this one-of-a-kind hike in southern Wisconsin is an absolute must for hiking and nature enthusiasts.

Holy Wisdom is a relatively new monastery (founded in 1953) of an ancient order with over 1500 years of history!

The nuns manage 130 acres of restored prairie and woodland overlooking Lake Mendota.

In less than 70 years, they have converted farmland back to natural prairie and are growing the oak forest back!

Their efforts can be seen throughout, and make it so that the Holy Wisdom Nature Trail definitely deserves to be on your list of southern Wisconsin hiking trails.

You can also stay at Holy Wisdom for personal spiritual retreats if you need time to yourself and it’s one of the most unique things to do in Madison, Wisconsin.

If a retreat here is of interest but unavailable, consider visiting one of the best yoga retreats in Wisconsin, many of which are located in Madison.

Book here the best tours in Madison, WI

6. Ice Age Trail: Blue Spring Lake Segment

Where: Palmyra, WI

Length: 7.1 miles

Difficulty: Moderate

best places to hike in southern Wisconsin, forest road among green trees in the mountains
Ice Age Trail forest path

Southern Wisconsin hiking trails include several segments of the scenic Ice Age Trail.

Choose the Blue Spring Lake trail for a solid physical workout, with a fair share of climbing up and down hills through a dense hardwood forest.

Some of the best mountain bike trails in Wisconsin are close by, and even horse-riding trails.

This segment is also near the territory of the Kettle Moraine, one of the best state parks in Wisconsin.

Start from the village of Palmyra, park at the Horseriders Camp, and get going.

Find the best scenic view on Bald Bluff, one of the highest points in Jefferson County at 1050 feet above sea level and 200 feet above the surrounding area.

The Bluff reportedly used to be a ceremonial dancing area for Native Americans.

This hike is one of the best day trips from Milwaukee because it is less than 50 miles away.

Book here outdoorsy RV rentals in Milwaukee

7. Moraine Ridge Trail

Where: Delafield, WI

Length: 7 miles

Difficulty: Advanced

Best hiking in southeast Wisconsin, Beautiful hillside of the Kettle Moraine State Forest in Wisconsin.
Kettle Moraine State Forest in Wisconsin
  • Accommodation Options: The Hidden Serenity B&B is a great hideaway. But a cabin getaway is the best way to enjoy the natural beauty here. You’ll love the GGG Log Cabin close to trails and the lake. The Lillibridge Lake Home is just steps from the water on quaint Tittle Lake, nestled in the Kettle Moraine State Forest.

This is one of southern Wisconsin hiking trails that are marked as difficult.

I picked it just for this, after warming up with a few of the easier places to hike in Wisconsin.

The 7-mile loop winds through the Lapham Peak Unit of Kettle Moraine State Forest, climbing several hills.

Start from the top of Lapham Peak, the tallest point in Waukesha County. Climb its 45-foot observation tower to enjoy a scenic view of this part of southern Wisconsin.

From there, follow the “Ice Age Access Trail” to the intersection with the Moraine Ridge loop.

Choose a direction: to the left for a hillier start across the forest, to the right for flatter sections of open prairie.

This variety offered me one of my best Wisconsin hikes. I got to see roe deers!

Lapham Peak Park is also a popular winter getaway in Wisconsin for lovers of cross-country skiing, with 27.8 kilometers of groomed cross-country ski trails.

Buy here the best Wisconsin itinerary

8. Kohler Dunes Cordwalk

Where: Sheboygan, WI

Length: 4 miles

Difficulty: Moderate

Best hiking in Southern Wisconsin, beach view of Kohler-Andrae State Park, Sheboygan
Kohler Dunes Cordwalk

The Kohler Dunes Cordwalk is one of the most original southern Wisconsin hiking trails and one of the most popular things to do in Sheboygan.

Visitors can find the Dunes Cordwalk in Kohler Andrae State Park, following the coastline of Lake Michigan.

Dunes, dunes, and more dunes! I was fascinated by the exotic scenario, sand-loving plants and flowers, and lots of different types of pine trees.

This unique landscape is one of the best hiking in southeast Wisconsin. The area is well kept, very clean, and equipped with benches, restrooms, and camping sites.

The Dunes are one of the most popular places to vacation in Wisconsin.

If you plan to stay nearby for a few days, check out my guide on the best hotels in Sheboygan and surrounding areas.

Book here the best cabins in Sheboygan

9. Mississippi Ridge Trail

Where: Wyalusing, WI

Length: 3.4 miles

Difficulty: moderate

best wisconsin hikes, confluence of mississippi and wisconsin rivers viewed from atop bluffs of wyalusing state park in driftless region of wisconsin
Confluence of Mississippi and Wisconsin rivers at Wyalusing State Park

My experience of southern Wisconsin hiking trails required a visit to the confluence of the Mississippi and Wisconsin rivers.

So, I headed for Wyalusing State Park, a 2,628-acre natural reserve that overlooks both river valleys.

The Park has one of the richest choices of hiking trails in southern Wisconsin, and some of the best mountain bike trails in Wisconsin.

The Mississippi Ridge Trail is used by both hikers and bikers.

For a panoramic view of Mississippi, I headed for the picnic area in Henneker Point, hiking through a forest of large maple and oak trees.

Wyalusing is great for southern Wisconsin camping, with several well-equipped outdoor campsites and an indoor camping lodge that can host more than a hundred people.

Camping lovers can enjoy one of the coolest weekend trips in Wisconsin right here.

Buy here the best Wisconsin hiking guides from REI

10. Old Immigrant Trail and Bluff Trail Loop

Where: Wyalusing, WI

Length: 3.5 miles

Difficulty: Advanced

hiking trails in southern wisconsin, view over lake missisppi from old immigrant trail
View of Mississippi River from Old Immigrant Trail

After completing the previous hike, I spent the night at one of the coolest southern Wisconsin camping sites: the Wisconsin Ridge campground.

This campsite sits on the bluff 500 feet above the Mississippi-Wisconsin confluence, and the overlooking views are stunning.

The next day, I hiked a loop of two trails, starting just from the camping site: two different environments – the bluffs and the river backwaters – packed in a very short distance.

Southern Wisconsin hiking offers so much diversity without the need to travel long distances.

I started with the bluffs trail, less than a mile but panoramic.

From there I walked down to the Old Immigrant Trail, back along the Wisconsin River, and up again to a grand close at the panoramic lookout point.

The die-hards who want more miles of the best hiking in southern Wisconsin can continue on the Sentinel Ridge Trail to get more panoramic views of the Mississippi.

Book here the best vacation rentals in Southern Wisconsin

11. Ice Age Trail – Holy Hill Segment

Where: Erin, WI

Length: 7 miles

Difficulty: Moderate

best hiking in southern wisconsin, segment of Ice Age Trail with yellow market on tree and a fallen branch
Tree marker along the Ice Age Trail

Hiking southern Wisconsin had some surprises for me, like Holy Hill; I would never expect to find a large Catholic basilica perched on a hill among forests and fields in the countryside!

The hill is a glacial “kame” formed by the retreating glaciers more than 10.000 ago and the highest point in Washington State.

French Jesuits “discovered” it in 1673 and planted across the area. Nearly two centuries later, Irish settlers built the first shrine of the Blessed Virgin Mary.

The modern church was built in 1930. More than 300.000 people come to this place every year.

Many of them hike the trail instead of simply driving there.

Beautiful woods surround the site, so visiting around October is one of the most awesome fall activities in Wisconsin.

Holy Hill is highly recommended as one of the best sites to see fall colors in Wisconsin.

Buy here the ultimate Like a Local Guide to Wisconsin

12. Scuppernong Trail System: Green Loop

Where: Eagle, WI

Length: 7.9 miles

Difficulty: Advanced

best hiking southern wisconsin, view of Scuppernong Creek
Scuppernong Creek

When you need a stronger, all-day workout in nature, what would be the best hiking in southeast Wisconsin?

The Green Loop of the Scuppermog Trail system is a good candidate.

The system, located in Kettle Moraine State Forest-Southern Unit, has three loops (red, yellow, green).

The Green Loop is the longest, and it will pump your heart well with some steep hills to climb, through hardwood forest and pine plantations.

The nearby Moraine Ridge Trail is a favorite horse riding trail. The whole Kettle Moraine Forest is an equestrian paradise.

If you are looking for unique Wisconsin vacation ideas, there are some ranches in Kettle Morain that offer horseback trail rides.

There are also several specialized campgrounds for horseriders.

Buy here the best hiking guides to Wisconsin

13. Chapel Gorge Trail

Where: Wisconsin Dells, WI

Length: 1.8 miles

Difficulty: Easy

best hiking trails in southern Wisconsin, Picture at the Wisconsin Dells
Near Chapel Gorge Trail in the Wisconsin Dells

This loop, starting from River Road, less than 2 miles from Wisconsin Dells, is one of the shortest southern Wisconsin hiking trails.

But I was happy to discover it because finding the best hiking in Wisconsin Dells is not so easy.

The Dells (including a 5-mile canyon of the Wisconsin River and some side branches) are gorgeous but have limited public access.

Part of the area is protected, while some iconic sites like the Witches Gulch and Stand Rock are private property, and you need to book a private boat tour to get there.

Chapel Gorge adds a taste of the Dells to your experience of hiking in southern Wisconsin.

Some of the characteristic sandstone rock formations of this area can be admired along the trail, and part of what this makes one of the best hiking Southern Wisconsin offers.

The trail leads to a lovely beach, close to the entrance of the Narrows, one of the most scenic canyons in the Upper Dells.

If you happen to be visiting with the whole family, Wisconsin Dells has some of the best family resorts in Wisconsin to relax and unwind after a long day of hiking!

Book here the best Wisconsin Dells tours

14. Gibraltar Rock Trail

Where: Merrimac, WI

Length: 4.8 miles

Difficulty: Moderate

hiking trails southern Wisconsin, Areal view from Gibraltar Rock trail during sunset hours
View from Gibraltar Rock

The Rock of Gibraltar has become quite the star among southern Wisconsin hiking trails in the last few years.

This flat-topped butte, with sheer cliffs dropping 200 feet, is the highest point in Columbia County,

Tourists that are only interested in the Rock and its panoramic view on Lake Wisconsin start from a parking lot that is only 1.4 miles away.

But they miss one of the best hiking trails in southern Wisconsin!

I took the longer trail that starts from the landing of the Merrimac ferry on Lake Wisconsin.

After crossing Highway 113, the trail begins a light climb across an area called Steenbock Preserve. Hilly terrain, forest and then prairie, and nice views of the lake.

Before entering Gibraltar Rock Country Park, you have to walk by the asphalt road for a while.

But the last scenic part is well worth it! The climb by the cliff is tough, somewhat dangerous (no rails!), and definitely one of the best hiking trails in Wisconsin.

The view up there is breathtaking, and I saw vultures circling in the air!

Book here the best vacation rentals in Wisconsin Dells

15. University of Wisconsin – Madison Arboretum

Where: Madison, WI

Length: 17 miles

Difficulty: Easy

hiking trails southeast Wisconsin, Arboretum in Madison, University Of Wisconsin.
Arboretum in Madison, University Of Wisconsin

No, you do not need to walk all the 17 miles of trails of the UW Arboretum.

But I wanted to drive your attention to the best hiking in southern Wisconsin in an urban center!

Hiking in Madison, thanks to this unique 1,200-acre green area, is one of the most amazing outdoor activities in Wisconsin!

The Arboretum is so huge that you can forget you are in the very center of the capital city of Wisconsin.

Restored prairies, savannas, woodlands, and wetlands: you get to see all these different environments and walk by the shores of Lake Wingra, the smallest of Madison’s five lakes.

I ran into dozens of turkeys strolling around but also got to see three sandhill cranes and lots of squirrels.

Visit during spring break in Wisconsin to enjoy cascades of blossoms everywhere.

It’s definitely the right place and time if you are looking for romantic getaways in Wisconsin.

Or come in October, because enjoying Madison’s Arboretum autumn colors is one of the most awesome fall activities in Wisconsin.

Book here the best tours of Madison

Why Go Hiking in Southern Wisconsin

Here are 3 reasons why you will love southern Wisconsin hiking trails:

  1. In southern Wisconsin you get so much diversity! Forests, prairies, wetlands, beaches, lakes, sand dunes, hills, rivers, canyons, cliffs, and spectacular rock formations.
  2. Enjoy wild nature a few miles from city centers. Or even within city centers. Discover the opportunities for hiking in Madison and hiking in Milwaukee.
  3. Fall colors. One of the most awesome fall activities in Wisconsin is hunting for places where to see fall colors in Wisconsin. The hiking trails southern Wisconsin are among the most colorful locations.

So, what are you waiting for? Please put on your hiking boots, and let’s get on those trails!

There was just one major drawback in my experience with hiking in southern Wisconsin…

… I could not get enough of it!

I tried hard to select the best places to hike in southern Wisconsin.

I am more than happy with what I saw. But I still feel that I left out so much.

There are so many amazing outdoor activities in Wisconsin that it is really difficult to choose. I will definitely come back for more.

Before You Go: Top Tips for your Trip 

Short FAQ About the Best Southern Wisconsin Hiking Trails

1. Where can I hike in Southeast Wisconsin?

Most of the Southern Wisconsin hiking trails are located in the southeast. But a few favorites are Kenosha Dunes Trail, Seven Bridges Trail, and the Scuppernong Trail System.

2. What are the best hiking trails near Milwaukee?

Almost all of these can be done as day trips from Milwaukee, but the closest are Seven Bridges Trail (just south of the city), and Ice Age Trail – Holy Hill Segment.

3. How long is the Ice Age Trail in Wisconsin?

The Ice Age Trail runs through all of Wisconsin and is approximately 1,200 miles long in total!