Find the top rated horseback riding trails in Illinois, 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.
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I just rode from my Chicago home to Racine on the North Shore Channel, Green Bay, R McClory and Kenosha County trails. The McClory is newly paved and well signed from the Great Lakes Naval Station north to the state line. There are no facilities other than the occasional bench, and there are long stretches without any shade. Otherwise it is a terrific ride!
I started the Jane Addams Trail at the RT 26 Junction and finished at the Wisconsin State border for a total of 32 miles round trip. Most of the trail felt like double track that was in very good condition due to the median of the trail being somewhat high grass, This did not make the ride difficult as both tracks are plenty wide for a gravel or hybrid bike to navigate with no issues.
I found the Orangeville trailhead to offer the most services along the trail. I'm sure the terminus in Freeport offers options as well but I did not explore that part of the trail. I also rode the Sugar River trail in Wisconsin and it is a great plus that one can ride the Jane Addams trail to the Beaver State Trail to the Sugar River Trail and beyond.
Both the North and South sections used asphalt and crushed stone surfaces. Care must be taken when riding on the crushed stone. The trail is nearly 12 foot wide and it is neatly groomed, however, the stone is just loose enough to keep bicycle speeds down. The rider who tests their speed traveling downhill and around the blind curves will surely tumble. The age of the asphalt in both sections varies from "newer" to "desperately in need of repair." The southern section actually has a warning sign just south of Fairfield Park.
The last two miles of the northern section in Round Lake Beach is loaded with perpendicular cracks in the asphalt causing a jarring ride even at slow speeds.
One must be cautious at the street crossings although some of the busier roads have traffic lights with designated pedestrian cross walks. The signage was ok, but could have been better.
Except for the 2 miles of crushed stone from Sheridan Road in Highland Park to County Line Road in Ravinia, the entire trail surface it asphalt!
The first 11 miles of the trail from the Wisconsin border is newer asphalt; no cracks or bumps to worry about. Just a smooth ride. The northern section of the bike path, however, is plagued with several street crossings, all of which must be approached with caution. There is little to no shade on the northern section.
The southern section of the bike path has a lot more points of interest including various sculptures along the trail, Metra train stations, the Ravinia Festival grounds and interesting cities to explore. The southern section offers much more shade, but also has a few street crossings as well.
The trail does give way to the road in both sections, but the signage is good for the most part. There are new mile markers on the west side of the trail every 1/2 mile.
Overall this is a good trail. We had e bikes with 22.5 tires and had no troubles riding. We started in Pana and rode up 7.3 miles. Paved 99% and it had many cracks that made it bumpy. It looks like the trail is not used much because grass was growing up through the cracks. Trail could use some maintenance. Not a lot to see on the south side of the trail. It was 95 degrees and most of the trail is shaded. This made it nice for the day we rode.
We rode the GAP from Cedar Creek Park to the Boston trailhead at the base of the Historic Boston Bridge and back. About 36 miles round trip. What a great ride. Smooth trail with lots of benches and several picnic areas and toilet facilities. Well maintained. Passed through several little communities along the trail. No major highways and very few little roads to cross making it very safe. Got a delicious huge “medium” size ice cream cone at the “Big Twist” in Blythedale, right off the trail. Highly recommend this ride!
(08/19/26) - Another beautiful day and a beautiful trail. Rode from Tutty's Crossing (Freeport) to state line (WI). Trail in great shape with no major defects to get in your way for a relaxing ride. The small town and countryside/farmland vibe is just outstanding. Especially if you're a small town kid like me. It's a true getaway from life kind of ride for a couple hours. Very little trail traffic and the scenery is gorgeous. As always, don't forget to treat yourself at Union Dairy after the 34 mile round trip. A great reward for a long ride.
We rode the full length from the Chicago Botanic Garden to the end at Foster Ave. and back. About 40 miles round trip.
Nice paved trail with plenty of washrooms along the way. Saw 8 deer at various points, two just standing on the side of the trail as we passed and never moved at all.
There is a $12 fee to park at the Botanic Garden, which was no big deal to us. There are plenty of free parking areas at the many forest preserves along the trail. Botanic Garden is great also, if you have the time to go through it.
The trail makes a loop around the Skokie Lagoons, but I would recommend only doing the east side. It has way better scenery and is quiet. Not so on the west side.
I took a star off for the following:
1. There are a lot of big road crossings. Golf road, Dempster, Touhy, and a really nasty diagonal one at Devon & Caldwell. All the walk buttons worked fine and you need to be patient, but they are wide and rather intimidating. The diagonal bridge over Oakton and US-14 is quite impressive though.
2. This is a greenway, so lots and lots of blind curves. This would not normally be an issue, but the road bikers are going too fast around them and there are a lot of pedestrians.
3. Other people have commented about the rude road bikers and we did encounter a couple of them. Most are courteous and tell you when they are coming by, but we had three at road crossings that pushed their way through and cut people off like they were going to a fire.
Over all, a nice trail and a great getaway for people living in the suburbs, but you've got to pay attention so it's not as nice as many sleepy rail-trails.
Rock island trail connects to rock island greenway through Peoria. Great ride but there are sections with some big bumps. Cool places to stop near/in Peoria Heights.
The route I chose took me 26.4 miles in and out beginning at Stonefort, Illinois and turning around at Breeden Trestle. This route also takes you through the tunnel while taking in many of the highlights of this trail. The trail was in good shape with the exception of one place where a tree had fallen and completely blocked the trail. Fortunately, the Park Rangers were out cleaning up from the storm. Ride it!
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