Find the top rated horseback riding trails in Sheboygan, whether you're looking for an easy short horseback riding trail or a long horseback riding trail, you'll find what you're looking for. Click on a horseback riding trail below to find trail descriptions, trail maps, photos, and reviews.
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I biked from Manitowoc to Two Rivers and back. The trail was well maintained and well marked. The views were spectacular. The road noise was not as bad as a previous review. There was no clear indication of where trail began and where it ended.
This is one of the smoothest riding trails you will find anywhere. Abundant marker posts so you always know how far to the next town. The stretch from Denmark to Maribel is mostly wooded, while the stretch south of that has more agriculture.
First time on this trail and it was a nice ride. My husband and I rode the whole trail starting from the south end to Denmark and back. There were a couple parks along the way as well as a bench here and there. Trees, rolling fields and a few bridges were the highlights of the scenery but the thing I enjoyed the most was how quiet it was. Even the roads we had to cross were quiet. The trail is very well kept and very well marked (quarter mile markers too).
05/10/2026 I parked in Medina road the Wiowash trail turned west on Friendship trail only road about .5 mile loose pea gravel and washed out I turned around went back to the Wiowash trail. I tried going east a couple weeks ago that is just as bad.
A lot of articles about upgrading the trail, so we did a 33 mile loop from Port Washington to Mequon. 3 miles was upgraded. The rest was filled with cracks, and bad crossings. We won’t be back. If your going to pave trails, verses limestone you have to upgrade them or they become a safety issue, and a very unpleasant ride.
A lot of articles about upgrading the trail, so we did a 33 mile loop from Port Washington to Mequon. 3 miles was upgraded. The rest was filled with cracks, and bad crossings. We won’t be back. If your going to pave trails, verses limestone you have to upgrade them or they become a safety issue, and a very unpleasant ride.
We rode the trail from Eden to a couple of miles past Campbellsport on a beautiful late September day and thought it was one of the best we've ridden. The trail was very well maintained, and the surface was solid despite recent rain. Although it's described as level, we did notice some definite up- and downhill sections with our heavy old tandem. Another note: contrary to the TrailLink map, there is a very nice restroom in the Eden Community Park, which is helpful if you need to change back into street clothes after your ride.
This is just a short trip from point beach down to two rivers but it’s a fun trail to run. Many small rolling hills and curves! We have e-bikes so not much of a work out but it sure is a fun trail. By far my favorite little trail this year!
If your doing a there and back deal start in Sheboygan, do all the uphill stuff and then coast back lol. This trail is ok for scenery, prolly really shines in Fall, quite a bit of hills. It does run along the highway the whole time, connecting Fondy and Sheboygan. Plenty of parking along the way.. bathroom at the Greenbush one. Parts of the trail are shotty between Plymouth and Sheboygan. Trail has no tree coverage but random covered spots to sit. Bike shop in Sheboygan Falls.
Really nice and taken care of. It’s a good ride there and back..about 13 miles. I’m sure beautiful in Fall. Love that I left right from my campsite at Long Lake.
Very nice and well maintained. I really enjoy this trail.
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