Find the top rated horseback riding trails in Shorewood, 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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Bike type: Hybrid (Specialized Sirus 2019)
Conditions: mid-70's, light breeze, dry
Segment biked: Just south of Algonquin to Barnard Mill Rd (north of McHenry) = 40 miles
I started my ride around 9:30am on a July Friday. I had biked a few miles of the trail just north of downtown Algonquin before, the rest was new to me. Perfect conditions motivated me in every way. Perfect temps, full sun, and breeze kept me going for my longest ride since 1997.
The entire path that I rode was asphalt. There are a couple of deviations through downtown areas when you're on sidewalks or streets. But everything was paved. Riding from town to town has always been a favorite, but the Prairie trail gie you even more than that. North of Crystal Lake you'll find miles on end of straight path and very little to see except nature. There's also Sterne's Woods, which really threw me for a loop. Can't say I've ever seen signs that tell bikers to dismount. Then you find out why. There are several hills back here to test your fortitude. At least three hills look to be close to a 45-degree angles. If you're riding these as I did, be careful and make sure you're only tempting them in optimal conditions (dry, no wind). Just coasting pushed me close to 40mph. These hills are as tough as they come to climb in Illinois. Algonquin, Crystal Lake and McHenry all offer pitstops if you need one. I saw two other parking lots away from the towns with benches and bathrooms. I had read from other reviewers that the path north of Barnard Mill Rd was gravel and dicey, so I didn't tempt that. My hybrid tires can hold their own, but it only takes one sharp piece of gravel to strand you far from your starting point. All in all, this path is a 10 out of 10 in my opinion. It's extremely well kept up, very diverse, ridable for any type of bike, with amenities and beauty along the way.
This bike trail is a straight shot from Lansing to calumet city Illinois.
We just completed the trail. What a Gem!!! Extremely smooth!!!!
This is my favorite rail to trail in the Chicago area. I ride a gravel bike. The wide open spaces and rural scenery is a relaxed vibe. I park at Sugar Creek Admin Center which has a nice parking lot and go all the way to the end just over the Kankakee River at Custer. My favorite section is the area that’s next to the Midewin Tall Grass Prairie. My tips for you if you’re going 40 miles round trip, water, a Gatorade, small snack. Folks on the trail are friendly and wave however once you get to the bridge crossing Hwy 102, things get weird. I don’t know why but the vibes are negative and you can feel it. I always want to see the river but again, bad vibes.
Highly recommend this beautiful and well kept trail. Beautiful to ride along the trees and over the 2 epic ohiopyle bridges.
Simple, short loop. You will end up sharing the loop with a lot more people when the weather gets good
Kankakee is half gravel half asphalt. It’s a perfect 15 miles so back & forth you can get a nice 30. Adding miles through town isn’t hard just watch the areas you go through. It is a BEAUTIFUL trail! It travels through Kankakee State Parks & along the Kankakee River. Some rises & falls, nice little hills. Cute bridges one big suspension bridge over a creek where locals swim in the summer. The far (NW) side of the trail has a pit toilet & an archery setup with a big stand. You ride through campgrounds, suburb sections, fairgrounds, parks, make sure to stop at the Indian Cave. Lots of photos ops along the trail. I really highly recommend checking it out!
I have been walking the woods around here for decades. The main bike trail is fine. Do not attempt to go in at jurgensen woods and try to head east though. Start at sweet woods across the street and stay on the main. Cook country forest preserve actively tries to only maintain the main paved bike trail. The very nice little jog which is shown here in jurgenson is not maintained at all and it’s a shame because it was a nice out of the way side quest 20 years ago.
Beautiful trail, love that it is more than 10 miles, but would not recommend for rollerblading. Much of the asphalt was cracked, and not sealed. It did not feel safe to be rollerblading on it, and did not love the vibrations from the asphalt shooting up my legs. Seems like a wonderful trail for walking/running/ and maybe biking.
You need to cross several major roads, but the ride is beautiful!
The trail from rusty nail north to Richmond was very rough and I lost the screws to my kick stand with all the bumps in the trail is there any plans to help smooth them out — I understand the horses share the trail but if they could help by staying to one side so us bikers have a chance on using the trail with out so many bumps dug into the paths¿
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