Find the top rated horseback riding trails in Oskaloosa, whether you're looking for an easy short horseback riding trail or a long horseback riding trail, you'll find what you're looking for. Click on a horseback riding trail below to find trail descriptions, trail maps, photos, and reviews.
Great trail, flat and smooth. Monroe has Jersey Freeze about 1/2 mile from trailhead- best ice cream esp the Van and Bonbon shake. Then Prairicty has Goldie’s restaurant which has the best tenderloin sandwiches and strips. The trailhead in prairie city is at west end of town by Casey’s gas. It has running water and real toilets . Has an oversized steel buffalo for a great photo shoot. You can continue your ride following the road to up and over the bridge to south of trailhead and then immediately left into the Neil Smith Wildlif Refuge- designated bike lanes on each side of roar and a 4+ mile pedal to the educational center. There are a few good hills to challenge you. Look to west and you might see the buffalo and elk.
Very nice trail but numerous sections closed for renovations. Good it's being maintained. Work in progress as of 6/30/2025.
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!
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