Explore the best rated trails in Winchester, KY. Whether you're looking for an easy walking trail or a bike trail like the Squires Road Trail and Legacy Trail (KY). With more than 8 trails covering 20 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.
Paved multiuser trail is short & flat. While not a destination trail, it is nicely shaded and worth a look if you are in the area.
Road from YMCA to the end of the trail by The horse Park was a great Trail to ride needed a few more markers and some places but overall great ride
Short trail that gives access to the surrounding neighborhoods. Connects to The Liberty Trail at the Man O War end & Walnut Grove Road at the other. Walnut Grove offers access to some nice country road riding
One of the best bikeways in the state. Rolling hills to the West, city access to the East.
Flat grade, wide path, and shade. Wonderful park about midway with restroom facilities. Amazing overpass to MOW. Exits to restaurants and ice-cream.
We started at the northern trailhead in an RV park next to the Kentucky Horse Park on I-75, a major thoroughfare. There’s a parking lot across the highway, but the actual start of the trail is marked by an obelisk within the RV park. We headed on a paved path toward the beautiful fields and paddocks of the Horse Park, only to have it end abruptly two miles later. Oops. Start in the parking lot across the highway. Or start in town so your round trip will end at one of the town's most popular taprooms.
If you’re a cyclist who’s into simply getting miles with some mixed topography with no regard to scenery or shade, this is for you. As a cyclist who simply enjoys exploring and tooling around, this was not pleasant for much of the joirney. Too much traffic, boring office parks, and LOTS of sun. It may be better in 30 years when the trees they’ve planted start to mature.
Great clean trail, easy to ride bikes. Paths wide and scenic.
We road a portion of the trail this morning. It is well maintained and very pleasant. There is lovely artwork built into the trail. We are novice bikers and this was a good trail for us as beginners.
Nice trail to connect the Legacy Trail/Hope Center Trail to the longer Legacy Trail and to town. Unless I missed it, it would have been helpful to me to know that the Coolavin Trail was also called the Legacy Trail. Makes more sense for the total mileage for the Legacy Trail.
Either there wasn't a sign for Hope Center Trail or I missed it when I crossed W Loudon Ave at the southern end of the Legacy Trail. I probably didn't do enough homework before my trip, and looking at this site almost 3 weeks after I biked it, I now learned that this short trail is named both Legacy Trail and Hope Center Trail. The red marked trail on TrailLink had Legacy Trail end at W Loudon Ave. Maybe there was a sign for Legacy Trail, which might have confused me, since I thought it had ended. Maneuvering through the gates by the railroad tracks was easy. When it T's into Coolavin Trail (which I learned on a map is also called Legacy Trail), the left/east will take you to an endpoint by a port-a-pot, where as the right/west takes you past the Coolavin Park until it ends. Some of the streets have green painted bike lanes, but even though I took a few of them, I really don't know where they go. All 3 trails make up the 12 miles listed under Legacy Trail (which had confused me if you read my review under Legacy Trail).
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