Find the top rated hiking trails in Sheboygan, whether you're looking for an easy short hiking trail or a long hiking trail, you'll find what you're looking for. Click on a hiking trail below to find trail descriptions, trail maps, photos, and reviews.
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Officially part of the Milwaukee County Oak Leaf Trail system, this connector joins the Oak Leaf loop at Brown Deer Park and meets the Ozaukee Interurban Trail seamlessly at County Line Road. Combined with the Oak Leaf’s Lakefront, River Line and Zip Line segments, they provide straight, smooth pavement on railbed between downtown Milwaukee and Cedarburg, and beyond.
Crushed stone was upgraded to asphalt by the end of 2022. Much smoother ride from end to end. Still absent a direct link into Lakeside Park.
On a perfect weekday morning in early October I experienced by bicycle the South Shore portion of the Oak Leaf Trail.
I parked in the Grant Park Beach parking lot in South Milwaukee and headed north to Cupertino Park and then back, a distance of about twelve miles. Even though it was such a short ride it took me over two hours since I had to frequently stop for the awesome photo ops. The views of the lake and the Milwaukee skyline are sensational!
The trail is obviously beloved by the community. Not only were there plenty of other bicyclists, but there were a tremendous amount of friendly pedestrians walking their dogs or getting their steps in, especially in Bay View Park.
The South Shore portion of the trail has so much to offer: woods, tree lined streets with charming homes, wildflowers, squirrels, geese, shoreline, lots of curves, five parks, yachts, and plenty of benches to take in the marvelous views of Lake Michigan and the downtown skyline. Besides the lake views, I especially enjoyed the curvy trail covered in golden leaves through the woods of Grant Park.
TWO WORDS OF WARNING:
1) There are hills.
2) There are cracked and uplifted portions of trail through the woods of Grant Park due to tree roots. They will effectively work like speed bumps and slow you down a bit.
However, all in all, this is an enjoyable ride and certainly worthy of your time and five stars!
We rode from Sturgeon Bay to about 3 miles past Algoma, then into Algoma and back to Sturgeon Bay. This trail is very smooth and well maintained, passing through some beautiful countryside.
I forgot!! If you wanna ride the trail in its entirety.. the gap is about 8 miles
A nice trail, well kept, just a little boring. I’m sure it’s time to shine is true fall with the leaves in full force. 0 bathrooms and tons of little black bugs atm.
trail is in perfect condition and while there were a fair number of users, it was never crowded or congested on this saturday morning. It was a joy to ride roundtrip from menomonee falls to north lake. The only steep hill is in merton just east of dorn road. The small towns of sussex and lannon have some taverns that look interesting. Menomonee park above the north part of the trail just west of lannon road is worth a visit.
Great trail for walk surface and natural sites.
First of all, the map on TrailLink doesn't show that the two trails are easily accessible via city streets in Two Rivers and the route is marked. This trail needs your attention at all times, with tricky turns and rougher terrain. The park at the north end is beautiful with views of Lake Michigan, but a majority of the trail is inland, with wooded views. When in Two Rivers head to the beach park, it is a WOW with phenomenal beach frontage and a large park for picnic areas.
Recently rode this trail two times. Stayed in Two Rivers and headed into Manitowoc for dinner and lunch. Stupendous views, beautifully landscaped with floral gardens and easy access to the downtown areas of both cities.
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