Find the top rated running trails in Winneconne, whether you're looking for an easy short running trail or a long running trail, you'll find what you're looking for. Click on a running trail below to find trail descriptions, trail maps, photos, and reviews.
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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.
Part of the trail has been resurfaced and all of the trail was in great shape. A beautiful ride along the Fox river.
Trail from Wittenberg to Birnamwood is grass covered crushed limestone. They do cut the grass, but not particularly bike friendly.
It’s a beautiful trail … well maintained! Quite a bit of shade for the most part we started In Fond du Lac off rolling meadows rd. Biked to the Horicon Marsh loop. I would recommend stopped at Katy’s Log Cabin in Oakfield for a good bloody and/or a great lunch !
The trail is well maintained and an easy ride. It follows the terrain. The views are beautiful. Lots of families either walking or biking.
Since the tornado in May 2025 there is two miles of trees down not far from Juneau. It is impassable. I rerouted from prospect onto Hwy 26 to Swan Rd.
I rode the entire trail from Seymour to New London and back in early June 2025. The trail is in super good shape and rideable with a road bike. There was a tree down across the trail about a mile west of Shiocton but easy to maneuver around. A really nice quiet ride in the countryside with no death machines. I rate it five stars. Traveling cyclist Facebook
We’ve done this trail twice and really enjoy it. Was attending a conference in SP and decided to bring bikes along. Weather was perfect for riding so we took advantage and rode this trail. It was wonderful. Love the variety of ‘environments’ you bike through, especially Schmeekle Reserve. The train is well maintained. Only delay was waiting on a train for 45 minutes!!
I did the Wiouwash Trail between downtown Oshkosh and Hortonville over two days while visiting family in the Oshkosh area, and the conditions were pretty great. Prior to this past weekend, I had only ridden the southern half of this segment. If you enjoy a nice (mostly) gravel trail that is very flat, you should have a great time on this one. The trail only had one small sketchy area of about 100 yards just south of County Road II near the gravel yard. Other than that, it's a really smooth trail.
I road a Salsa Fargo on this visit with 29x2.2" tires, but have also done it on an All-City gravel bike with 700x38 tires. Both work just great, and I'm guessing you could easily get by with tires down to 32-ish mm.
There is a nice mix of fields and forested areas along with a few wetland locations. I happened to see quite a few deer, turkey Canada geese, two trumpeter swans and even a couple of Cooper's hawks hunting along the trail, one successfully.
It is probably also worth mentioning that I rode this trail on a Saturday and Sunday in good weather conditions and saw ZERO other bikers, which was more than a little surprising, but there were plenty of people walking dogs at various points along the trail.
Big thumbs up for this trail. Consider getting out to enjoy it if/when you are able.
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