Explore the best rated trails in Sheboygan, WI, whether you're looking for an easy walking trail or a bike trail like the Oak Leaf Trail and Milwaukee RiverWalk . With more than 40 trails covering 541 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.
Great for walking/running/biking, not great for rollerblading. Needs resurfacing for sure. Parking is best ad Badger Sports Park
I biked from the starting point just south of downtown West Bend to the endpoint in the village of Eden. The surface of the trail for the first 5 miles in West Bend was nicely paved. The trail during this stretch was 12' wide and smooth. The canopy of trees not only provided a good supply of shade, but it also created a park-like ambience. There were many photo opportunities in downtown West Bend, especially next to the Museum of Wisconsin Art building. There were a couple of busy roads to cross, but the worst was Washington Street (Hwy 33). Take Caution!
The trail changes to a hard-packed crushed stone just north of downtown West Bend. The trail narrows to 6' wide most of the way to the endpoint in the village of Eden. There is an occasional road to cross, but these were not heavily traveled. The village of Kewaskum provided a needed change of scenery and a nice rest stop.
The first two bridges I encountered in West Bend were new, but the rest of the bridges on the trail were heavily patched and, quite frankly, in need of replacement. Overall, the ride was peaceful and fairly easy.
Like the Eagles 1972 hit song, this well-established trail was both peaceful and easy. I biked from Oshkosh to Hortonville and back. The trail was mostly nestled under a canopy of trees. The sides of the trail were mowed and I did very little tree-branch ducking. For the most part, the trail surface was solid and bone dry. Beware of the section next to the mountain of sand in Clayton. Some of the sand has drifted onto the trail causing slippery conditions. The loop around the Fox River Inlet in Oshkosh was a nice change of pace. On the east side of the Fox River by Hwy 21 is the Fox River Brewing Company. They have a large outdoor dining area that includes a beach house and tiki bar!
We accessed this trail from the Lakeside Park trail. We were a little unsure of where to go until we got the areas which were well marked. It’s mainly city roads but there is a wide bike path off the road most of the time. Lots of neat old buildings.
This connected us to the Pioneer Trail which has 2 interesting roundabouts at the beginning of the trail. More city riding but you can stay off the street on the sidewalk.
Then we connected up with the Camelot trail. This trail starts out in the suburbs, you go past a pond and through a park. More peaceful ride.
Then you ride on a bridge over Hwy 45 / Fond du Lac Ave to get to the south end of the Prairie Trail which is by the Fond du Lac Waterworks Water Tower in a residential neighborhood.
We did this trail as part of the Fond du Lac loop trail system by going in a counterclockwise direction and following the Fond du Lac Loop signs.
We started on the north end of the Prairie trail at the Park N’ Ride/ Prairie Trail Lot on Winnebago Drive just off Hwy 151.
We took a right at the fork to bike the Peebles trail which ran into the Harbor view trail. We then took a detour through Lakeside Park on the Lakeside park trail. Then ended up going through the city on the Brooke street trail which ran into the Pioneer trail, another city trail. Which in its turn ran into the Camelot trail which took us over a bridge to the other end of the Prairie trail. A very nice loop. The trails are color coded and pretty well marked.
We accessed from Peebles trail. Paved.
Starts out on Harbor View Drive where you are supposed to use the bike lane in the street instead of the sidewalk. Then can go through a park if you want. Not sure of the parks name. There is a nice view of lighthouse and lots of boats.
Then took a detour through Lake side Park on the Lakeside Park trail which has nice bathrooms. Lakeside Park trail was very nice. There were some nice bridges over the streams, a covered bridge, an operating small train for riding around the park, and a barn.
We then got on a street going past the city yards where there was mulch, etc. I think it was the start of the Brooke Street Trail. Basically we followed other bikers.
We did this trail as part of the Fond du Lac loop trail system by going in a counterclockwise direction and following the Fond du Lac Loop signs.
We started on the north end of the Prairie trail at the Park N’ Ride/ Prairie Trail Lot on Winnebago Drive just off Hwy 151.
We took a right at the fork to bike the Peebles trail which ran into the Harbor view trail. We then took a detour through Lakeside Park on the Lakeside park trail. Then ended up going through the city on the Brooke street trail which ran into the Pioneer trail, another city trail. Which in its turn ran into the Camelot trail which took us over a bridge to the other end of the Prairie trail. A very nice loop. The trails are color coded and pretty well marked.
We parked at the Park and Ride at Hwy 151 and Winnebago Drive which is the north end of the Prairie trail. We took the right fork to get on the Peebles trail. A short trail but peaceful. Trees and greenery on both sides of trail. Saw 3 deer. Connects you to the Harbor view Trail.
We did this trail as part of the Fond du Lac loop trail system by going in a counterclockwise direction and following the Fond du Lac Loop signs.
We started on the north end of the Prairie trail at the Park N’ Ride/ Prairie Trail Lot on Winnebago Drive just off Hwy 151.
We took a right at the fork to bike the Peebles trail which ran into the Harbor view trail. We then took a detour through Lakeside Park on the Lakeside park trail. Then ended up going through the city on the Brooke street trail which ran into the Pioneer trail, another city trail. Which in its turn ran into the Camelot trail which took us over a bridge to the other end of the Prairie trail. A very nice loop. The trails are color coded and pretty well marked.
We parked at the Park and Ride at Hwy 151 and Winnebago Drive which is the start of the north end of the trail. No bathrooms but there is a gas station/ restaurant on Winnebago drive which has a bathroom. This trail mostly runs along 151 but is buffered in areas by a pretty wide berm which sometimes had trees and other greenery on it. Other short areas separate you from Hwy 51 with a short concrete wall. Nicely paved. It’s pretty nice for a trail that runs along a highway. Better than Friendship trail.
There is a bench and drinking fountain at the south end by the Fond du Lac Waterworks water tower. We had fun turning on the bubbler and watching shoot about 8 feet in the air.
We did this trail as part of the Fond du Lac loop trail system by going in a counterclockwise direction and following the Fond du Lac Loop signs.
We started on the north end of the Prairie trail at the Park N’ Ride/ Prairie Trail Lot on Winnebago Drive just off Hwy 151.
We took a right at the fork to bike the Peebles trail which ran into the Harbor view trail. We then took a detour through Lakeside Park on the Lakeside park trail. Then ended up going through the city on the Brooke street trail which ran into the Pioneer trail, another city trail. Which in its turn ran into the Camelot trail which took us over a bridge to the other end of the Prairie trail. A very nice loop. The trails are color coded and pretty well marked.
This 8 foot-wide asphalt trail meanders through urban neighborhoods. Although the trail is broken up in a few sections by roads, there is plenty of unique artwork to see. My favorite ride in the city!
One of my favorites! Well packed, some hills and curves. A section with cedars on either side, another section where the trees form a canopy above. Truly enjoyable, ending at Point Beach where you can watch the waves of Lake Michigan crash in on a sandy beach. 5-stars for sure!
We picked up the trail in Maribel and rode to Denmark, then rode back toward the other end. We didn’t quite finish it. On the positive—the trail is fairly well maintained. Not much traffic. It’s well marked and there are distance markers every 0.25 miles. A combination of fields, farms and trees, and some nice wooden bridges. Not as positive—some of the gravel is not well packed down. The drop off on the sides on the section from Maribel to Denmark is a bit steep and you shouldn’t take your eyes off the trail. Some of the intersections with roads involve a steep grade up, which makes it difficult if you don’t have an e bike. An ok trail but not our favorite. Also wish it had some ports-Johns along the way.
We started in downtown Menomonee Falls. We parked in Mill Pond Park on Roosevelt, then rode our bike over to Water Street where the trail begins. That probably wasn’t the best place to start because we had to cross the two scary intersections; Highway 175 with a crossing light and Main street on a long diagonal with no crossing light.
This is a very nice trail with wooded areas that pass through residential areas and some business areas. The northern end has some fields. On the southern end you have to stop to cross at a lot of roads all the way to and through Sussex. Luckily the car drivers are very courteous and stop to let you cross. It was nice to see kids of all ages on the trail. It’s pretty flat until you get past the Fireman’s Park soccer fields in Merton. Then you have some pretty steep hills.
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