Find the top rated dog walking trails in Waupun, whether you're looking for an easy short dog walking trail or a long dog walking trail, you'll find what you're looking for. Click on a dog walking trail below to find trail descriptions, trail maps, photos, and reviews.
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Nice enough trail to get from the Wiouwash to Neenah area but very bumpy.
We took this trail from the Wild Goose trail but had no idea we would be on so many roads. As you got closer to Watertown, you are also on the road. We personally try to avoid roads as much as possible so we didn’t like this part. We only went to Watertown from the North so I am not sure what the rest of the trail is like. The actual bike paths are great.
from Medina to Allenville 05/19/26 there’s a section between county II and county T that’s very muddy especially by the gravel pit it’s always muddy and from Allenville to Oshkosh it’s a better trail
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.
9/13/25 We began at the east end of the Lower Yahara Trail and then picked up the City Trail from there. Both trails were in exceptional condition. Traffic was busy, however the weather in mid-September in the low 80's certainly brought people out. A very friendly trail by anyone's standards. Well worth the 50 minute drive to get here. This is the second September we've rode this trail.
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.
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