Find the top rated trails in Sheboygan, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.
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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...
The Konkapot Creek Trail is a short gravel pathway that follows the winding tributary of the Fox River through Kaukauna. On its south end, the trail connects directly to the CE Trail, which travels...
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...
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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 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...
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...
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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...
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...
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...
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 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...
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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...
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 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 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...
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 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 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,...
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 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 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 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 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...
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 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. The trail follows 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 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 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 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...
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 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 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 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 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...
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...
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The Prairie Trail offers a 7-mile, paved route cupping 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 shore of...
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 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 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...
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 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 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,...
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 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 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...
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 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 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 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 Mascoutin Valley State Trail is divided into two segments along a former corridor of the Chicago and North Western Railway. The eastern section runs 10 miles between Fond du Lac and Rosendale. 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 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 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...
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 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 Oak Leaf Trail has so many branches and so many good places to ride. I was riding the Grant Park-South Shore section since I was a kid when it was the 76 trail. We ride that section a lot still but it can be crowded with bikes, runners, and walkers. Most bikers are polite and understand the need to ride single file, but it seems like a lot of groups when there are more than a few just don't get it. One of the best things is riding from Grant Park to the South Shore Beer Garden!
We also ride from Drexel Ave. to County Line Rd. Beautiful, especially once you get south of Ryan Rd.
Another leg we enjoy is from the Milwaukee County Sports Complex on Ryan Road to Whitnall Park, especially now that there's a permanent beer garden there as well. On this leg of the trail once you get about 1/4 mile north of the sports complex it follows the Root River. You hardly see any houses or busy roads and you really feel like you're out in the sticks.
Moving in just behind the beautiful flower fields.
Struggled to find trail in Menasha. The trestle bridge is nice, really nice. But both sides of the bridge, not so nice. Won't do it again.
I rode a southern leg of the trail from Oak Creek to the Racine County line and back. There's marked street parking on Drexel Avenue, where the trail intersects. The trail is wide and blacktopped all the way south through well-kept neighborhoods and wildflower fields. There are some minor hills in Oak Creek, as the trail dips down and then rises back up as it crosses roads. The trail heads east for a while along Ryan Road until it continues south through scenic wetlands to County Line Road, where there is a parking lot and conservancy hiking trails across the road.. I took a ride along County Line Road westward, skirting the Root River, and connected with a trail spur that continued west to Howell Avenue. I stopped there, but met a bicyclist who said that the trail now continues into an industrial park for a mile or two. But I retraced my tracks back to my car at Drexel Avenue. The hills in Oak Creek seemed a little harder on the way back. But all in all, it was a pleasant 16 mile round trip on a summer day.
The trail is perfect. I can go wherever, whenever on my bike or by my foot. The thing is, it's too small. Groups of three or more are too common here, and that leads to some very close calls. When there is a group of 20 seemingly professional bikers who look like they're going at a speed I will never be able to get to, vs. me who's biking at a super casual speed, surrounded my pools of mud, and nature is not so nice in that situation. It's happened to me. It wasn't nice. Otherwise it's a perfectly nice trail.
My wife and I enjoyed the Devil's River State Trail this afternoon. We encountered a fair amount of rain, and this made the wet gravel a bit more difficult. So we were tired by the time we finished. Our bike computers said we did 29.75 miles for the round trip, though officially the trail is shorter than that.
We were initially surprised to discover that downtown Denmark had a festival going on, so it was busy. But parking was still available at the trailhead. I was impressed; it is a nice park for the trailhead.
We liked that trail mileage markers were posted every quarter mile.
One thing though. Heading south from Denmark all trail markers say XX.XX miles to Rockwood. We were sort of expecting something interesting at the Rockwood trailhead, but there were no services and no signs. You just get there, take a water break and snack, and turn around. My advice would be to start this trail in Denmark and do as much as you have energy for, but don't force yourself to go to the very end.
The whole trail is beautiful, but I sort of think the nicest parts are in the northern section.
The Oak Leaf trail from Grant Park north to Milwaukee has to be one of the nicest stretches in the entire 120 mile system. On a sultry summer day, I parked in the golf course lot at Grant Park in South Milwaukee and headed north on the trail. It winds through woods and fields and offers beautiful views of Lake Michigan from the tall bluffs. There was a welcome cool breeze off the lake. The trail was smooth blacktop all the way, with a few hills. Later, it passes along the lake through the towns of Oak Creek, Cudahy, St. Francis and Bay View. At South Shore Park in Bay View, the trail heads down to the beach and the South Shore Marina, a good place to stop and take a break. I rode up to Bay View before the Hoan Bridge and then headed back. A great ride of 18 miles.
The Oak Leaf Trail has both positives and negatives, however positives do outweigh the negatives. This trail allows users to travel through the heart of Milwaukee, however the lack of bike lanes and signage when the trail segments off makes it difficult for people unfamiliar with the area to find their way around. Being a resident of the Milwaukee area for 16 years, the trail is not so challenging for me to figure out, but this does prove to be a downfall of using the Oak Leaf Trail. On the other hand, the trail is nicely paved, full of wildlife, and the users tend to be friendly, so it does make for a great atmosphere! My advise when using the Oak Leaf Trail would be to review the map and o plan your route beforehand, especially if you are unfamiliar with the Milwaukee area.
Started this summer at the Custer Lane parking lot (4 cars max). Walked to the Meno Falls starting point, then walked back and then south down the trail and back to the car. Played leapfrog like this all the way to Merton and the newest extension to the end.
Man, I feel so much more physically fit, look better & clothes fit much better too. And it's only costing me gas money and time. What a bargain.
I could have biked, but wanted to take pics and enjoy myself instead of racing through the trail. No fun in that. Thanks Bugline for the memories.
jf2641.
We had a great time on this trail. Everyone we met said hi and were very courteous. We ride around Madison quite often and get run off by racers all the time and no one ever says Hi. The trail is paved and very well maintained.
Scenic, peaceful, and a journey through of Wisconsin's beauty.
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