Explore the best rated trails in Sheboygan, WI. Whether you're looking for an easy walking trail or a bike trail like the Brown Deer Recreational Trail and Eisenbahn State Trail. With more than 33 trails covering 492 miles you’re bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
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The Downtown Trail—also known as the River Trail and Riverwalk Trail—runs alongside the Fond du Lac River for nearly 2 miles in the heart of Fond du Lac. The vast majority of the trail is smooth...
The Eisenbahn State Trail gives a nod to Wisconsin’s German heritage in its name—Eisenbahn is German for “railway.” The strict translation, “iron road,” refers to the iron rails originally used as...
The Peebles Trail is a nearly 6-mile pathway, linking Fond du Lac at the southern edge of Lake Winnebago with St. Peter (Taycheedah) to its east. The trail also passes through the unincorporated...
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The Prairie Trail offers a paved route of nearly 7 miles along the eastern boundary of Fond du Lac, a mid-sized city befitting its French name which means “foot of the lake” as it hugs the southern...
The Harbor View Trail occupies a former rail bed—now shared with overhead electric transmission wires—on the southern edge of Lakeside Park in Fond du Lac. The trail parallels Harbor View Drive for...
The Beerline Trail, so named because the corridor was once used by freight trains transporting the ingredients for beer to some of Milwaukee’s famous breweries, has contributed to the revitalization...
The Kohler Memorial Drive Path is a straight paved path that rides adjacent to the Kohler Memorial Drive. Starting at the American Red Cross, you can ride for just under a mile on the outskirts of the...
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The Old Plank Road Trail parallels State Route 23—a road originally built out of wooden planks in the 1800s—from the western edge of Sheboygan to the Village of Greenbush. The trail was one of the...
Loop the Little Lake, or the Loop, is a 3.5-mile circle of trails, bike lanes, sidewalks and parks around the lower half of Little Lake Butte des Morte in Wisconsin, just north of the larger Lake...
The Rawley Point Trail is a winding, hard-packed limestone pathway from the harbor town of Two Rivers on the shores of Lake Michigan to Point Beach State Forest. The 6-mile, sometimes hilly, trail...
The Friendship State Trail will eventually run between Stevens Point and Manitowoc in eastern Wisconsin. Currently, two disconnected segments of the trail are open for use. In the east, a 4-mile...
The Sheboygan Interurban Trail follows the route of an electric railway that once ran between Milwaukee and Sheboygan from the early 1900s to 1951. The trail begins at Pebble Beach Road on the Ozaukee...
The Oak Leaf Trail is the jewel in the crown of Milwaukee County’s extensive trail system. The trail meanders for more than 120 miles in and around the city of Milwaukee on a changing terrain of flat...
Appleton’s Newberry Trail follows the Fox River, its navigational canal locks and an active rail line at different points during its scenic trek. The area was once an industrial hub, but mature trees...
The Fox River State Trail connects Packerland with pastureland as it rolls for 25 miles from the hometown of NFL’s Green Bay Packers to farming communities south. Named for the river that spawned the...
The Wild Goose State Trail is a premier rail-trail, spanning approximately 35 miles in Dodge and Fond du Lac counties. If you are looking for a peaceful and beautiful place to visit, this trail has it...
The CE Trail, one of the longest trails in the Fox Valley region of Wisconsin, links Appleton and Kaukauna along busy County Highway CE. While not particularly scenic, the trail offers access to a...
The Milwaukee RiverWalk provides a pleasant way to get around Milwaukee from the Historic Third Ward, through downtown, and north to the Lower East Side. It also has easy connections to three other...
Wisconsin’s Wiouwash State Trail is named for the four counties it passes through: Winnebago, Outagamie, Waupaca and Shawano. Currently, 41 miles of the rail-trail are open in two disconnected...
Fond du Lac's Brooke Street Trail follows a former rail corridor from the community's southern reaches to an endpoint not far from scenic Lake Winnebago. The city's location relative to the lake,...
Taylor Drive Multi-use Path is a 2.75-mile trail in the heart of Sheboygan, Wisconsin. The trail stretches from Crocker Avenue to Kohler Memorial Drive (SR 23), providing a north-south non-motorized...
The Prairie Trail offers a paved route of nearly 7 miles along the eastern boundary of Fond du Lac, a mid-sized city befitting its French name which means “foot of the lake” as it hugs the southern...
Fond du Lac's Brooke Street Trail follows a former rail corridor from the community's southern reaches to an endpoint not far from scenic Lake Winnebago. The city's location relative to the lake,...
Travelers on the Mariners Trail will be spoiled with beautiful vistas of beaches, parks, forests and the sparkling waters of Lake Michigan. Supplementing the scenic landscapes are several trailside...
The Harbor View Trail occupies a former rail bed—now shared with overhead electric transmission wires—on the southern edge of Lakeside Park in Fond du Lac. The trail parallels Harbor View Drive for...
The Kohler Memorial Drive Path is a straight paved path that rides adjacent to the Kohler Memorial Drive. Starting at the American Red Cross, you can ride for just under a mile on the outskirts of the...
The Devil's River State Trail stretches more than 14 miles, connecting the towns of Denmark, Maribel, Francis Creek and Kossuth in eastern Wisconsin. The trail is a scenic jaunt through farmland,...
The CE Trail, one of the longest trails in the Fox Valley region of Wisconsin, links Appleton and Kaukauna along busy County Highway CE. While not particularly scenic, the trail offers access to a...
Appleton’s Newberry Trail follows the Fox River, its navigational canal locks and an active rail line at different points during its scenic trek. The area was once an industrial hub, but mature trees...
Loop the Little Lake, or the Loop, is a 3.5-mile circle of trails, bike lanes, sidewalks and parks around the lower half of Little Lake Butte des Morte in Wisconsin, just north of the larger Lake...
The Brown Deer Recreational Trail runs through the Village of Brown Deer, a suburb of Milwaukee. The tree-line route parallels an active rail line through commercial and residential areas. Mid-way,...
If you’re going to visit the historical communities that lie just west of Lake Michigan, why not use the former route of the venerable interurban railroad? The Ozaukee Interurban Trail stretches the...
The East River Trail winds for just over 6 miles along its namesake waterway through the communities of Green Bay, Bellevue, Allouez, De Pere, and Ledgeview. Its first section was developed in 1990...
The Wild Goose State Trail is a premier rail-trail, spanning approximately 35 miles in Dodge and Fond du Lac counties. If you are looking for a peaceful and beautiful place to visit, this trail has it...
The Peebles Trail is a nearly 6-mile pathway, linking Fond du Lac at the southern edge of Lake Winnebago with St. Peter (Taycheedah) to its east. The trail also passes through the unincorporated...
The Oak Leaf Trail is the jewel in the crown of Milwaukee County’s extensive trail system. The trail meanders for more than 120 miles in and around the city of Milwaukee on a changing terrain of flat...
The Shoreland 400 Rail Trail opened in 2013 on a former Union Pacific Railroad corridor through the heart of Sheboygan. More than 30% of Sheboygan County’s residents live within a mile of the trail,...
Broad blue skies strung with white cloud wisps; gem-green fields harboring cattails and butterflies; canopied glens giving way to cavernous quarries. It's all part of the ride on the Bugline...
The Ahnapee State Trail in northeast Wisconsin provides a scenic 45-mile journey between Sturgeon Bay and Kewaunee, featuring a tour of water bodies along the Door Peninsula. It also overlaps two...
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The Lake to Lake Bike Trail takes you through the beautiful terrain of the Kettle Moraine State Forest. It is a newer, well-maintained trail, with a wide, crushed limestone roadbed. It is used daily...
The Downtown Trail—also known as the River Trail and Riverwalk Trail—runs alongside the Fond du Lac River for nearly 2 miles in the heart of Fond du Lac. The vast majority of the trail is smooth...
The Shoreland 400 Rail Trail opened in 2013 on a former Union Pacific Railroad corridor through the heart of Sheboygan. More than 30% of Sheboygan County’s residents live within a mile of the trail,...
The Friendship State Trail will eventually run between Stevens Point and Manitowoc in eastern Wisconsin. Currently, two disconnected segments of the trail are open for use. In the east, a 4-mile...
If you’re going to visit the historical communities that lie just west of Lake Michigan, why not use the former route of the venerable interurban railroad? The Ozaukee Interurban Trail stretches the...
Broad blue skies strung with white cloud wisps; gem-green fields harboring cattails and butterflies; canopied glens giving way to cavernous quarries. It's all part of the ride on the Bugline...
The Ahnapee State Trail in northeast Wisconsin provides a scenic 45-mile journey between Sturgeon Bay and Kewaunee, featuring a tour of water bodies along the Door Peninsula. It also overlaps two...
The Oak Leaf Trail is the jewel in the crown of Milwaukee County’s extensive trail system. The trail meanders for more than 120 miles in and around the city of Milwaukee on a changing terrain of flat...
The Eisenbahn State Trail gives a nod to Wisconsin’s German heritage in its name—Eisenbahn is German for “railway.” The strict translation, “iron road,” refers to the iron rails originally used as...
The Beerline Trail, so named because the corridor was once used by freight trains transporting the ingredients for beer to some of Milwaukee’s famous breweries, has contributed to the revitalization...
The Rawley Point Trail is a winding, hard-packed limestone pathway from the harbor town of Two Rivers on the shores of Lake Michigan to Point Beach State Forest. The 6-mile, sometimes hilly, trail...
The Brown Deer Recreational Trail runs through the Village of Brown Deer, a suburb of Milwaukee. The tree-line route parallels an active rail line through commercial and residential areas. Mid-way,...
The Old Plank Road Trail parallels State Route 23—a road originally built out of wooden planks in the 1800s—from the western edge of Sheboygan to the Village of Greenbush. The trail was one of the...
Fond du Lac's Brooke Street Trail follows a former rail corridor from the community's southern reaches to an endpoint not far from scenic Lake Winnebago. The city's location relative to the lake,...
The Kohler Memorial Drive Path is a straight paved path that rides adjacent to the Kohler Memorial Drive. Starting at the American Red Cross, you can ride for just under a mile on the outskirts of the...
Located in Sheboygan at the South Pier, the Lakefront Bike Path begins off Indiana Avenue and connects on to the Pier Boardwalk. The trail is right off the shores so users have a pleasant ride or walk...
The Peebles Trail is a nearly 6-mile pathway, linking Fond du Lac at the southern edge of Lake Winnebago with St. Peter (Taycheedah) to its east. The trail also passes through the unincorporated...
The Prairie Trail offers a paved route of nearly 7 miles along the eastern boundary of Fond du Lac, a mid-sized city befitting its French name which means “foot of the lake” as it hugs the southern...
Wisconsin’s Wiouwash State Trail is named for the four counties it passes through: Winnebago, Outagamie, Waupaca and Shawano. Currently, 41 miles of the rail-trail are open in two disconnected...
The Wild Goose State Trail is a premier rail-trail, spanning approximately 35 miles in Dodge and Fond du Lac counties. If you are looking for a peaceful and beautiful place to visit, this trail has it...
Appleton’s Newberry Trail follows the Fox River, its navigational canal locks and an active rail line at different points during its scenic trek. The area was once an industrial hub, but mature trees...
Very nice trail that connects several parks with many different athletic facilities. Follows along the river closely. Only downside is parts of the trail may be flooded when the river is high.
We rode on October 22, sunny 45-50 degrees. We started in Ripon from the little lot off of County E. The trail was in good condition and there were plenty of benches but no Port-o-Potties. The first part parallels County E so you cross some driveways, but it's no big deal. After a mile or so you leave the road and head into the Wisconsin farmlands. There's even a Winery that you can visit along the way....not sure what that would do to my ride :-) Beautiful ride with a stop at Berlin for lunch at a very nice and tasty Mexican restaurant.
Couple of caveats: There's a landfill along the way that will get your noses attention, and a shooting range both of which you circumvent just south of Berlin. Just hope the sportsman didn't visit the winery beforehand! :-)
My husband and I decided to take up biking and this was our first trail ride and we really enjoyed it. I have a small dog and she travels in a pet basket and she also really enjoy the three hour ride. Mostly gravel but well maintained.
A great trail, very pretty even on the in-city parts riding through the woods. There's plenty of shade and the paved surface is great for my recumbent trike. The trail is well marked and drivers were super courteous about stopping when I needed to cross. I stopped and had a nice swim at Menomonee Park
I started this trail in Denmark and rode the entire length of the trail. At Denmark, it was well marked with rest stop facilities. The trail is a very pretty trail. You see lots of wildlife as well as farm animals. It is a well maintained trail. My only complaint is that the end of the trail in Rockwood could be marked better. There are a number of buildings that may be confused for a parking lot for the trail.
I started this trail at Forest Junction and road it into Green Bay. It was an excellent trail. I started out on the gravel portion which lasted about half of the journey. Once I got into brown county, there were rest stops and places to purchase your trail pass. Trail passes are only required on the Brown County portion of the trail (I had verified this with a person at the Calumet Couty parks office).
I thought this segment of the trail was a very good trail. Well marked in Brilllion. Although, there were some portions of the trail that had small weeks growing through, I thought I was well maintained. I hope they are able to connect the segments soon.
The Shoreline 400 is an execellent trail to ride. My only problem with it is that it’s too short.
The old plant trail was good trail over all. Some areas on the western side had weeds growing. Very hilly! You notice it traveling west. Lots of rest stops
I wrote the entire length of the Sheboygan Interurban Trail . In general, it was an excellent trail to ride. However, As the previous person who posted earlier, the trail is about 50% on the road. That was disappointing. The road was good to ride and not full of potholes.
First let me start by saying the Oak Leaf trail is an excellent trail that circles Milwaukee county. I have been using this trail ever since it use to be called the '76' trail. Unfortunately, I haven't been on the south end in years. I recently decided to go south(starting at Greenfield park) with the intent to get to the newer of Milwaukee Counties parks, Bender park. When I got to Drexel at which point I would normally go straight east toward Grant Park I found I was able to continue South. Not having checked the trail map prior to my adventure I made the assumption that the ability to go further South of Drexel would somehow meander its way to Bender park. Unfortunately I was mistaken. Needless to say I managed to get to Bender park by going East on Ryan Rd./Hwy 100. I eventually got back on the Oak Leaf trail down near Grant park after heading North from Bender park through South Milwaukee on 5th Ave. Let me once again reiterate how awesome the Oak leaf trail is and how I should have checked the map prior to my excursion. As an avid biker I can only hope that at some point there will be an extension/offshoot of the Oak leaf trail that will allow bikers to safely get to that corner of Milwaukee county via trails.
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