Find the top rated snowmobiling trails in Sheboygan, whether you're looking for an easy short snowmobiling trail or a long snowmobiling trail, you'll find what you're looking for. Click on a snowmobiling trail below to find trail descriptions, trail maps, photos, and reviews.
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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.
Very nice and well maintained. I really enjoy this trail.
Part of the trail has been resurfaced and all of the trail was in great shape. A beautiful ride along the Fox river.
We came to Milwaukee specifically to ride this trail. Over the course of three days I put a little over 100 miles on my bike, which did include some backtracking. I'd say we rode maybe 60% of the trail. The majority of what we rode was gorgeous and incredibly well maintained. In particular, the lakeshore section from South Shore park to Grant Park was incredible. The Whitnall Park/Root River route on the western edge of the Oak Leaf loop was also a wonderful ride. We rode from riverside park out to Glendale; if you do this portion make sure to ride up into the Arboretum, it was amazing. (And you will find restrooms there). On a less positive note , the East/west route that bisects the Oak Leaf Loop was barely a trail, more o
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 !
We drove our bikes from the Manitowoc Maritime Museum up to the harbor in Two Rivers. The ride goes right along side a very busy highway next to many beaches of Lake Michigan. So for us the only downside if the ride was traffic noise which meant we had to shout any communication. But the views are very beautiful. We saw more pelicans in one afternoon than probably the entirety of our lives. There are beautiful flowers along the trail, restrooms and places to access the beaches. For us it was the ideal ride. The West of the Lake Garden that you pass by is a must stop location, it is free but park by the bike racks and no carry-ins allowed.
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.
Started at the depot in Oostburg and headed north. After a few blocks we re-checked the app and saw it was just a bike *route*, not really a trail. We turned around and went back. No idea why this is considered a trail. It’s just a bike route. I don’t mind sharing with cars for short sections but I don’t consider riding busy country roads for miles worthy of “trail” designation.
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