Find the top rated hiking trails in Oshkosh, 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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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.
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
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.
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.
It’s pretty scenic, especially with the leaf colors. Also pretty busy! There’s parking on both ends. A lot of the trail is grass, not even gravel. The spot where it’s asphalt is very minimal. It’s awesome you can stop and ride through Horicon Marsh! Lots of kitties on this trail ¿
Rode from Point Beach State Forest campground. Fun, hills and turns that are fun to navigate. Hard packed and well maintained trail.
I have ridden this from Brown Deer to just a bit past Port Washington and still need to do the whole thing. On the Soutern side where it starts its no different than say, Zipline or the Brown Deer connector. But once you start getting close to Cederburg, it starts to shine, with a dip in scenery when you transition through Grafton. Then the trail SHINES BRIGHT right into Port Washington. This and Bugline are probably my favorite rides in the greater Milwaukee area.
Fun ride through the woods. The trail is in much better condition than it was a few years ago. There are a lot of wooden board walks over the swampy areas. The trail is tough in spots, we were glad we had wider tires and stable bikes
Fun ride through the woods. The trail is in much better condition than it was a few years ago. There are a lot of wooden board walks over the swampy areas. The trail is tough in spots, we were glad we had wider tires and stable bikes
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