Explore the best rated trails in Oskaloosa, IA, whether you're looking for an easy walking trail or a bike trail like the South Tama Recreation Trail and Red Rock Prairie Trail . With more than 25 trails covering 193 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 Cinder Path is one of Iowa’s hidden gems. I’ve ridden trails all over the state and Midwest, and this is still one of my favorites. It’s in great shape—smooth, fast, and well-maintained, with solid bridges and beautiful scenery. The covered bridge is a standout feature, and the rustic, unpaved surface adds to its charm. It’s quiet, remote, and feels like a true escape into nature. The communities of Chariton, Derby, and Humeston are lucky to have it.
This is not a MTB trail but also isn't a paved bike trail. I've ridden it after heavy rain and it was fine, road it last week in some light rain and it was in great shape. Grass section near Humeston was in good shape and not overgrown.
The trail is in the best shape I've ever seen it and I would recommend this to anyone.
We rode the full trail from Washington to Keota, Over all a great afternoon ride. A couple of gophers holes to dodge, but the trail is in pretty good shape.
Nice easy flat ride with a lake on one side and housed on the other
I rode the Chichaqua Trail in early October 2024. From the southwest end to 88th street east of Bondurant is smooth cement. There is parking and a restroom at 88th st where it changed to asphalt with a few minor issues. The worst part was between Ira and Baxter. Just watch for cracks. Some bad spots are paint marked. Overall a great long trail away from noise and traffic that I would highly recommend riding. I give it 5 stars! Traveling cyclist Facebook
I found this trail while riding the Fairfield loop that it intersects with on the south side. It’s a nice well packed crushed stone trail with a couple nice bridges and a pit toilet along with benches. I only road the off road part of the trail as I turned around when it changed to gravel roads. I rate this trail 5 stars. Traveling cyclist Facebook
I rode this trail in late Sept 2024. I started at 9th street and Gear Ave and attempted to ride clockwise but the trail was closed near Chautauqua Park and I got lost on the detour so I rode through town back to where I started and rode counterclockwise. I was going to ride around to the closing on the other side but I got side tracked by the Cedar View Trail which was also great. The Loop is a treasure for the people that live in the area. Much of the in town parts are paved and the rest is smooth crushed rock. I give this trail 5 stars! Traveling cyclist Facebook In
I rode the Kewash in late Sept 2024. It’s paved from Washington up to the bridge at Crooked Creek where it changes to good crushed stone. There were a very few holes that some animals have dug here and there but overall the crushed stone is in solid great condition with no loose gravel. There is a lot of straight open riding with no shade. It’s a very serene ride with no interaction with the death machines. I rate this 5 stars for sure. Traveling cyclist Facebook
I thoroughly enjoyed riding this trail in early August 2024. I rode every direction and back more than once. I really liked the old bridge with the eagle blind. If I lived here I would ride this everyday. Five stars!
Traveling cyclist
Facebook
I rode this trail the first of August 2024. This is the epitome of a great trail. I would recommend riding this world class trail. The trail is broken but the road sections are well marked and easy to navigate. A lot of shade as it winds through woods and gentle hills. I would give it more than five stars if I could!
Traveling cyclist
Facebook
I most recently rode the trail on the end of July 2024 from Howell Station Campground to the termination by Cordoba Park. It’s a wonderfully curvy and hilly trail. The hills are long and gentle and the views are great. It seems most of it was shaded. There were some cracks but most of it was smooth and any cracks were manageable. Going the other direction from my start would take you into Pella which is mostly uphill and not a lot of shade. I would highly recommend this trail my favorite being the part I ride along Lake Red Rock. traveling cyclist Facebook
I stumbled upon this trail exploring the Summerset State park and it was a very pleasant surprise all the way through! Wonderfully paved with blacktop (with only a couple clearly marked bumps here and there) it passes sweeping countryside vistas of farmland/crop land as well as long stretches of tree tunnels and woods. My favorite part was passing over the charming wooden trestle bridges going over the rushing streams and babbling brooks. My only regret was that I didn’t do more of the trail, I’ll definitely check this out again when I’m passing through the area.
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