Find the top rated horseback riding trails in Woodstock, 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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My buddy and I rode the trail from Big Hill Park to downtown Janesville yesterday. What a great ride. About 60% of the trail is shaded. The blacktop three miles or so from Janesville is heavily cracked and rough but not too bad. The first 9mi it’s a very smooth trail. We’ll be doing this one again.
This is the portion that is most scenic. Part of the trail from Burlington to Rochester was closed
I've been biking this trail for over 30 years at varying degrees of fitness. It is in part, protected from sun with shade and also from wind. This offers a reprieve from really hot days with heavy wind. It can get congested so being aware of others and biking courteously is important. There is pedestrian traffic that occasionally has no clue it's a shared path, as well as the over enthusiastic cyclist that equally behaves rudely. Most people however are genuinely out enjoying nature and each other.
We came to Milwaukee specifically to ride this trail. Over the course of three days I put a little over 100 miles on my bike, which did include some backtracking. I'd say we rode maybe 60% of the trail. The majority of what we rode was gorgeous and incredibly well maintained. In particular, the lakeshore section from South Shore park to Grant Park was incredible. The Whitnall Park/Root River route on the western edge of the Oak Leaf loop was also a wonderful ride. We rode from riverside park out to Glendale; if you do this portion make sure to ride up into the Arboretum, it was amazing. (And you will find restrooms there). On a less positive note , the East/west route that bisects the Oak Leaf Loop was barely a trail, more o
The pavement of the Chicago section between Foster north to Lincoln is in very rough shape, and has only deteriorated since I started using the trail regularly last September (2024). Another priority could/should be the addition of some bridge overpasses (more underpasses are probably not feasible) so that trail users could avoid having to cross several busy (and only getting busier) intersections from Devon all the way up and into Evanston. It has some really enjoyable sections, though, and some stretches in Lincolnwood/Skokie have been recently repaved.
I’ve been walking and cycling this trail for most of my life and it’s always a wonderful experience, such beautiful scenery along the river. It’s by far my favorite trail in the Chicagoland area.
Rode the Busse Forest trail on a busy, sunny Saturday morning in late June 2025. The surroundings are terrific but the asphalt has many cracks that made the ride a bit bumpy. Still it is a great ride and I encourage everyone to try it. There are elks there although I didn’t see any.
Rode part of the Prairie Part starting in Warrenville a couple of days after substantial rain in June 2025. The trail had some very minor puddles but was in great shape. When in Warrenville don’t miss the great bike shop where I got some excellent advice about which way to go on the trail. Highly recommend this route. Thanks to the bike shop guys!
I did this trail on bike 2 years ago and I hated it, signage is terrible, at one point after Golf road, you literally come to an end and have to carry your bike over train tracks and active train tracks. No signs of any sort. You go through a campground that confuses you even more. I won’t do it again. To ridiculous.
Like other reviews, I agree too many red lights that take forever to change, the smell of the garbage plant near by stinks, it’s an ok trail to walk but bike ride, no. You’ll be done in 20 minutes. From Devon to Greenbay road. I give it 2 stars for riding 4 for walking.
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