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.
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 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
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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.
I rode this short trail that is at the end of the Somerset Trail in 2024. It’s a nice little trail. Traveling Cyclist Facebook
I rode this trail in June from Carlisle to Indianola and back and again in July in the reverse and back both done in 2024. I love this trail! Very scenic and well maintained. You can tell it’s an older trail but still a very good surface and enjoyable. When in the area I recommend riding this trail. Traveling Cyclist Facebook
The majority of this trail is well paved with a bit of street riding needed. Nice mix of park-like and country setting with small bits of hill climb. Was surprised to read a sign saying no fast biking allowed only to meet a golf cart on the path. Would highlight recommend this path for an hour plus ride.
Overall I was pleasantly surprised at the scenery and variety along this trail. I started at the Maasdam Barns (next to the Health Center) and went clockwise. The first issue I encountered was a closure at Kale Blvd a little over a mile in. I didn’t see any indication the trail was going to be closed at this area ahead of time. Fortunately there wasn’t a work activity at the time and others had been going around the barriers. The other trail closure at Chautauqua Park had better signage for the detour. The trail was a mix of crushed limestone, concrete path and a section of gravel road.
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