Looking for the best trails around Charleston?

Explore the best rated trails in Charleston, IL. Whether you're looking for an easy walking trail or a bike trail like the Greenbelt Bikeway and Montezuma B&O Walking Bridge. With more than 26 trails covering 91 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.

Recent Trail Reviews

Parke Community Rail Trail

So much fun!

May, 2023 by hsrector224

Nicely paved and well maintained. It looks like it’s about to expand and I can’t wait to see where it goes!

Lincoln Prairie Grass Trail

First longer ride of 2023

April, 2023 by shellijennings

Nice way to spend a beautiful day biking 16+ miles on an asphalt trail. They are currently doing work putting in new telephone poles.

Wabashiki Trail

great location

February, 2023 by jtibbett

Enjoyed the ride no issue with dogs Good parking area with restrooms I would do it again

Accordion

Lincoln Prairie Trail

Use extreme caution on parts of trail

November, 2022 by graywolf14

Heavy leaf cover and branches and other debris from trees completely cover the pavement in many areas along the trail which require very slow and careful navigation when on a bike. Stopped several times to either walk bike through rough patches or to pull twigs lodged between tire front fender. This trail is not maintained at all and needs a thorough sweeping by villages or organization tasked with keeping trail in a safe and reasonably maintained condition for the enjoyment of everyone whether biking or hiking.

Kickapoo Rail Trail

Enjoyed a beautiful ride through fields East of Urbana, IL to St. Joseph. Paved approaches to road crossings and nice surfaces for the trail. Multiple bike stations for minor repaira and free at the East end at the Casey's.

August, 2022 by coachclark1

Enjoyed a beautiful ride through fields East of Urbana, IL to St. Joseph. Paved approaches to road crossings and nice surfaces for the trail. Multiple bike stations for minor repaira and free at the East end at the Casey's.

Lincoln Prairie Trail

There are sections of this trail that are very rough. After a few miles...I just gave up beating me and the bike to death. This could be a beautiful trail if it just had some repaving and trimming.

July, 2022 by jmrkav

There are sections of this trail that are very rough. After a few miles...I just gave up beating me and the bike to death. This could be a beautiful trail if it just had some repaving and trimming.

Lincoln Prairie Trail

Beautiful Trail In Need of TLC

July, 2022 by andrems

We enjoyed our first out and back ride on the Lincoln Prairie Trail on a hot and sunny morning. First the positives. Beautiful farmland scenery over a 13.5 mile straight line from Pana to Taylorville. Tree cover is intermittent and very welcome on a sunny day with the exception of a 2 mile long open stretch just east of Taylorville. There are a number of really beautiful stretches where you’re going through a tunnel of trees along the way. For those looking for a flat trail, this fits the bill. Over our 27 mile out and back ride we gained a mere 250 feet of altitude. As for the less positive elements, the pavement varies between good and poor condition. The opening 2 miles from Pana is pretty rough with lots of grass and weeds growing through cracks in the pavement. In other areas there are a lot of cracks and bumps that detract a bit from the ride. Be aware that there are no amenities along the path. Use the restroom at the McDonalds in Pana before starting as the porta-potty at the Pana parking lot is not very nice. Also be sure to pack water and a snack as there is no where to get something along the way. Despite the negatives, we really enjoyed our ride and will be back. If you love beautiful farm scenes and a flat ride you should enjoy the Lincoln Prairie Trail. When we reached the north end near Taylorville we were greeted with an imposing concrete barrier that keeps you from crossing a small bridge and completing the last mile into Taylorville. I hope they can raise the funds to repair the bridge as it would really be nice stop for a refreshment before returning to Pana.

Lincoln Prairie Grass Trail

wonderful trail

July, 2022 by deb.hutti

100 percent ashphalt! Straight with nice towns on either end. New bathroom stop 1/2 way. Great length and a nature center at one end. Worth the effort.

Wabashiki Trail

First experience on trail not good!

July, 2022 by gciolli4940

In the first mile today was met by two unleashed dogs near VCSC building. On my return the same two were charged me and my pet (who was leashed). I fortunately had a poop scoop with me to fend off both dogs. Contacted WTH Police Dept. who indicated they were familiar with the dogs around the area of 4th & Olive. Not blaming the dogs and will give benifit of doubt to owners who may not have been aware the collared dogs were loose. Just want future guests of park to be aware of the risk they may encounter and to be prepared just in case.

Wabashiki Trail

First experience on trail not so good!

July, 2022 by gciolli4940

One mile from bro walk in WTH, was attacked by two neigh hood dogs (4th & Olive). Luckily had poop scoop with me and was able to fend off. Again on way back same to dogs. Reported to WTH police who were familiar with dogs. Will wait a few weeks to see if owners take responsibility before attempting another walk. Landscape looks awesome and well maintained. Just be aware if you have children or pets !!!

Lincoln Prairie Grass Trail

very nice functional trail but nothing extraordinary about it

June, 2022 by bicyclegary_tl

If you happen to be in Charleston IL then definitely visit it, but don’t go out of your way to visit it It is in very excellent condition, 95% paved despite the photo on this website Straight as an arrow, one slight turn in 11 miles. Very nice nature center about 3 miles from end in Mattoon Il.

Lincoln Prairie Grass Trail

Trail is great, but needs shade and wind barriers.

April, 2022 by spikeman2k55

The trail is great, but needs shade and wind barriers.

Find Nearby City trails

Accordion

Register for free!

Register for free with TrailLink today!

We're a non-profit all about helping you enjoy the outdoors
  • View over 40,000 miles of trail maps
  • Share your trail photos
  • Save your own favorite trails
  • Learn about new trails near you
  • Leave reviews for trails
  • Add new and edit existing trails

Get the Free TrailLink App

The trail is always better with TrailLink

Scan the QR code to get TrailLink on your phone

Explore by City

Explore by City

Explore by Activity

Explore by Activity

Log in to your account to:

  • View trail paths on the map
  • Save trails to your account
  • Add trails, edit descriptions
  • Share photos
  • Add reviews

Log in with Google

Log in with Apple

OR

Register for free!

Join TrailLink (a non-profit) to view more than 40,000 miles of trail maps and more!

Register with Google

Register with Apple

OR

Your account has been deleted.