Explore the best rated trails in Plainfield, WI, whether you're looking for an easy walking trail or a bike trail like the Levee Trail (WI) and Green Circle Trail . With more than 15 trails covering 283 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.
I rode a recumbent trike from Howard to Pulaski. The trail was in good condition and a fairly smooth ride.
The trail is mostly beautiful. Almost all crushed gravel, which we didn’t expect. In some parts the gravel is thick and loose. The only asphalt is on county roads. the concrete, as expected, was on sidewalks in town. The boardwalks were fun but be careful if you are riding on 3 wheels. If I hadn’t just rode the Heart of Vilas and the Root River State Trails, which are as close to perfect as you can get in this region, I would’ve given the Green Circle a 5 star review.
We ride trails. We love trails. No pavement required. We embrace the crushed surface. We love to bike. The Omaha trail is surrounded by beautiful scenery. It begins and ends in friendly towns. It was strewn with debris the day after a storm, yet we were undeterred. You can bike around debris. Sadly, you can’t miss the ridges, ruts and roughness of a once paved trail. Omaha stole our energy and joy of riding. We rode on because we don’t quit. But it wasn’t enjoyable and was only memorable for the relief of finishing and knowing we won’t ride Omaha again. It’s unfortunate. The 400 is nearby. It is a far better choice, as is just about any other trail.
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.
If you’re looking for a nice quiet ride either segment of the trail is great! The fondy-Rosendale was better than the second half of the trail in my opinion.
One of the best trails I have risen around here so far. Great distance that takes you through all sorts of different scenery and is easy to ride!
The trail has some nice parts , however it goes through town a lot and some parts are not clearly marked which way to go. Some parts are washed out so can be difficult to keep steady in those areas.
We rode the entirety of the trail in 2.5 miles and we’ve never seen a more clean, well-maintained, and marked walking/biking path. Top notch! Highly recommended!
Lots of shade and curves. 90% on trail and 10% on non-busy roads. Trail well taken care of. Mostly limestone with many wooden bridges. A few busy intersections to cross though but all had traffic lights. Be careful though because some of trail is made for a single rider and not enough room for an oncoming biker to go by. A few speedsters on trail, so take those curves (some blind curves) slowly and carefully. Lots of absolute stunning scenery at every turn. I loved it, minus those speedsters¿¿¿¿¿
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