Find the top rated hiking trails in Charleston, whether you're looking for an easy short hiking trail or a long hiking trail, you'll find what you're looking for. Click on a hiking trail below to find trail descriptions, trail maps, photos, and reviews.
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This is one of my favorite trails and I’ve probably biked over a hundred. It’s a good workout and also relaxing because it’s straight, mostly flat, and bordered by wildflowers and butterflies. I’d avoid the town portions in both Mattoon and Charleston, going park to park from the east of Mattoon to the west of Charleston. This is still about a ten mile stretch each way. There is only one crossing that’s at all iffy - the top of a hill both ways just east of the golf course. Otherwise just a super calm ride.
I recently moved from a rural area in Parke County to Terre Haute.. I had no idea that the Parks and Recreation dept of Terre Haute had so many well kept trails and areas. The Heritage Trail is a phenomenal trail to bike. Mostly shaded and surrounded by nature this is truly a gem!!! The ride is very pleasant and enjoyable. From Blakey trailhead to Jones trailhead it is entirely paved. Much wildlife to be observed. It is approximately 7 miles round trip with numerous places to stop, rest and sit on a bench. To me this is HEAVEN!!!
The Bridge is fixed full trail now
Covered bridge Gateway Trail in Rosedale, Indiana keep you updated
The segment east of Charleston is not paved. It's only a mile but if you are a trail completionist, be prepared for a rough ride for that mile or and back. Closer to a field road than a trail.Rest of the trail was perfect.
Had a wonderful bike ride with the family. It was a hot day, but the shaded trail made for a delightful time. We parked at S Llama St where there is a small gravel parking lot, unloaded the bikes and rode the 1.6 miles to the bridge just East of S Canal St. that crosses a creek. The scenery in summer was great and the newly updated bridge was well done. An added bonus was all the trail crossings over the streets were stamped concrete that resembled the rail crossings that used to be there.
The Lincoln Prairie Grass Trail pavement has been extended 6 blocks further west to the YMCA parking lot and a beautiful new park on 16th Street.
Noisy traffic but nice views from the boardwalk. Extend your walking buy going south through Fairbanks park on the east side of the Wabash bridge.
I’ve walked this multiple times, both alone and with grandkids. Parking is excellent and there are picnic table and benches at the site and on the Wabash bridge itself. The high sides of the first portion of the former railroad bridge obstructs views but it opens up to steel trestle for scenic river views. Beyond the bridge the trail is enjoyable with tributory on the left and woods/fields on the right. Unfortunately the trail ends at the active railroad tracks and a picnic table. Plans to extend are apparently underway. Train watching is fun at the terminus. Make it a real walk by walking through the nearby parks, downtown, and stopping at the Tasty Freeze for great ice cream.
My first trail ride from near the Vermilion County Fairground to the west edge of Oakwood. Very nice ride. Nice scenery along the route. I only wish it was completed so I could go all the way to Urbana.
With construction of the new trail bridge over the Flat Branch starting in September (2024), the trail will soon be restored to its full 14.6-mile length, with access points at the Taylorville Trailhead, Lake Taylorville (Lake Point Veterans Memorial) parking lot, Owaneco, and the Pana Trailhead.
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