Explore the best rated trails in Cherokee, IA, whether you're looking for an easy walking trail or a bike trail like the Tatonka Ska Trace and Sandy Hollow Recreation Trail . With more than 33 trails covering 199 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 started at the northern most end at 300th street just south of Fostoria after reading a previous review that the trail extended further than the map showed. I rode 7.5 miles before I was actually riding the trail on the map. I then rode from 18th street that shows to be the north end south and then turned west until the T intersection at 355th street in the west and back. It was a very enjoyable 22 mile ride.
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I rode around West Okoboji using some roads on the east side before rejoining the trail. The following day I again rode around the lake staying on dedicated trail by joining Tatonka Ska Trace trail which connects to the GLT at 155th street in the west and at Peoria street in the east. From there you can head also head north to Big Spirit Lake. In the south at 202nd street you can ride south to Milford or take some streets to reconnect at Three Cross road.
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A mile or so south of Lake View the trail is closed for another mile. Not to worry. You can take the highway south just short of the RR tracks, and take the gravel road to the end. The trail starts up again there.
I rode this trail numerous times in early August 2024 in perfect weather. Each time I started from Emerson Bay Recreational Area. I rode south around West Okoboji but where the trail ends I got lost and ended up riding the shoulder if Hwy 71 to get back to the trail on the other side. I rode south to Milford and back. My second outing I rode n north until the trail ended on the map in the app so I followed Lake Shore drive around the lake until I met the trail again. Third time I rode north again and realized I could continue north and connect to the road Tatonka Ske Traceti connect back to the IGL trail.
We really enjoyed this ride. Since we rode in March there was not any foliage on trees or landscape. But the trail condition was smooth sailing all the way.
This is a wonderful bike trail that goes all the way around West Okoboji to the north taking the old railway—beautiful Iowa prairie with wild flowers, all the way to Spirit Lake. Then it goes south to East Okoboji, Hwy 71 with a nicely paved trail. Not always marked well but once you know the way, it’s a piece of cake. 26 miles around West and East Okoboji. We love it!
Wow! This is a trail worth ridding. We started out in Carroll and rode up and back to Breda, then down and around Swan Lake state park. The next day we went from Lake View to Breda and back. The trail is all concrete, they have replaced all the sections that were asphalt. We had a great time.
Paved and well maintained trail that follows Perry Creek from down by Hard Rock Hotel, and goes all the way to Outer Drive. From there you can take Outer Drive and connect to Floyd River trail if desired.
Thank goodness for the TrailLink app bc this trail is very poorly marked. Pay attention to white spray painted arrows to guide you bc there is very little signage. The majority of the trail is asphalt or blacktop and sections are along the major US 71 highway. We parked at the Milford end of trail trailhead and there is no parking. We pulled into the grass along the road. Overall very shaded and nice and would recommend but have you TrailLink app ready to guide you!
My husband and I (and our brother-in-law, a Sheldon resident) rode some of the trail this morning, starting out near the schools and then crossing over Rt18 to ride through some scenic areas — a park, some neighborhoods, lots of trees and even past a cow farm, with an up close view! The trail goes under Highway 18 at the Floyd river, and continues to the community college. We turned around at the fork that would have taken us to the college, and headed back the same way we came. The current trail connects the college, the schools, and parks. Future goals for the trail are to complete it on the south side of the highway, so that it forms a loop all the way around the city. The newest phase loops around the pond right behind Crossroads Pavilion Event Center, near the intersection of H18 & H60 on the east end of town. (This doesn’t show up on the trail map yet.) All of the trail is paved. There are a few areas where you ride on a couple of neighborhood streets until you pick up the trail again. The trail developers have added some really nice touches — benches, a gazebo, an arched entryway at Hills Park created from bricks that were salvaged from Sheldon Middle School. They’ve done a great job, it was an enjoyable ride.
What a great trail! We explored the trail over two days. We started in Lakeview and went down to Brenda for a really enjoyable 30ish mile day. This portion of the trail is in great condition and passes through some wildlife preserve, protected marsh land, and natural resource management areas. We saw an incredible amount of wildlife. Check out a little café called Kays for some homemade pie. For a second day we started at Brena and went down to Caroll, Iowa. This portion of Trail is not as good condition as the northern section. The views are really pretty and the greed is still there were so slight that it’s virtually flat. This portion of the trail has a lot of exposed areas that could be a bit of a challenge if there was a strong wind.
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