Explore the best rated trails in Sheboygan, WI. Whether you're looking for an easy walking trail or a bike trail like the Fox River State Trail and CE Trail. With more than 38 trails covering 507 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.
The trail is along Lake Michigan and is beautifully paved and landscaped. But being along a four lane highway makes it less enjoyable.
Did the whole Southern segment. Was a decent trail..the usual trail trail..nothing spectacular. The part of the trail running along the water is pretty. Low rating is for the all the horse **** up n down the entire trail. The leaves this time of year really hide the piles.
This trail is one of the smoothest, well maintained rides in the area. Yes, it is gravel but no washouts or ‘loose’ gravel . Kudos to the people that maintain this beautiful trail.
This is a great trail. It’s super fun with the small rolling hills n going through the woods. The cabin is cool to see too. U pop out in the state park to see a nice view of Lake Michigan.
Out of all the trails I’ve done, I like this one the least. Half of it’s in town and on side streets with poor signage. Once you hit the gravel part, it’s super shotty for the first 2 miles since they redid culverts n put new gravel in..I’m talking huge sharp stones that are loose. Once u get past that the rest of the decently packed gravel trail runs along the highway. I was also lunged at by some Boxer who was potentially trying to bite my ankle. It was on a leash but the owner could not control it..she just looked at me n walked away.
It’s a nice trail..the gravel is a bit loser than the ones I’ve been on. There’s not much for bathrooms along the way but there’s nice parking right at the trail head. At the end there’s a small parking lot too and u see where the old railroad use to continue. Colors r nice along this trail.
I started in Greenbush and went to Sheboygan. It came out to 17.2 miles, one way. Overall the surface is smooth with only a few places that were just a little rough. Lots of hills, which are normally great, because no matter how much it hurts going up, you can always coast down. Except that at the bottom of most of the hills, you have to stop at a road crossing. The views of the Kettle Moraine Forest from the hilltops were nice as the Fall colors are starting to come in. Yes, being right next to Hwy 23 was noisy and smelly from the exhaust. Overall though, I enjoyed the ride. Plenty of spots to stop and rest. A river. Wide open farmland. I guess this trail could suck or be fantastic, depending on one's expectations and perspective.
The Milwaukee County Parks, Oak Leaf Trail webpage says the extension of the South Shore Line segment is open to Bender Park. It is not yet show on the TrailLink map. On my September 2022 trip up to the Oak Leaf Trail, to do the original South Shore Line and the Oak Creek Line, I decided to see what the new extension was like. Yes, it is open with routing signs in place and a creek bridge constructed. But the surface is made up of 1-inch sized crushed stone which is typically used as a base layer under asphalt pavement. Even though I have a gravel bike, from Drexel Ave I only made it down to Pennsylvania Ave and gave up the going further. It’s just too rough. I made the trip back using highways. I searched on the internet, and it seems that the funding grants describe a 2023 completion. I hope what is the case is the asphalt paving will be done in 2023.
On my third trip up to the Oak Leaf Trail I did what I call the Southeast Quadrant. I parked at Greenlawn Park and did the trail and spurs down to the Racine County line and up to Cupertino Park near the Lake Michigan Ferry. What I liked about this trip was the variety in the trail. Segments consisted of rails to trails (with powerlines), trail in parks, separate trails on arterial streets, the parkway roads, and rural highways. The long, southerly segment in the forest on the bluffs along Lake Michigan was the prettiest segment of my three trips on the Oak Leaf Trail. The north segment along Lake Michigan was closer to the water and gave a nice view of downtown Milwaukee.
One concern is the trail is being extended to Bender Park, which is popular but what about funding of maintenance of the trail that already exists? This section had some of the asphalt showing its age with the periodic shrinkage cracks giving that frequent bothersome bump. One hidden path bridge at the bottom of a hill had plywood covering over rotted deck boards, which at speed was very rough. But none of these maintenance issues should stop any one from coming to use the Oak Leaf Trail. I do recommend stopping at the coffee/ice cream store the trail parkway passes at Chicago Ave.
I am sure the rail to trail segment from Greenlawn Park was the former North Shore Interurban Line (to Chicago) that my folks took on their honeymoon to Milwaukee in 1944.
Great trail; all paved. Lots of things to do along the way; many different stopping places available!
Love this trail! Can find several restaurants to eat at, play miniature golf, get a great cup of coffee all on the trail! Great trail!
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