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.
_208216_st.jpg)
_155683_st.jpg)
_208216_sc.jpg)
The Legacy Trail runs north-south through Lexington among green spaces, neighborhoods and parks. Two highlights of the popular pathway are the Lexington YMCA and Kentucky Horse Park, which features a...
_155683_sc.jpg)
Town Branch Trail in northwest Lexington currently extends between Leestown Road and Alexandria Road, following an old railroad corridor between a subdivision and cultivated fields. Plans call for...
Although short in length, the Hope Center Trail provides an important connection between two other trails in Lexington’s northern neighborhoods. The paved, 0.3-mile pathway gets its name from the Hope...
The Brighton East Rail Trail was Fayette County's first, opening in 2007. The original 1-mile trail through recent residential development between Bryant Road and Pleasant Ridge Park proved...
The Coolavin Rail Trail runs for a half mile in northern Lexington's Smithtown neighborhood. The paved pathway begins on a quiet street adjacent to the Transylvania University Athletics Complex and...
Liberty Park heads north from the west end of the Brighton East Rail Trail in Lexington. Following Liberty Road somewhat, the trail crosses Star Shoot Parkway, where it provides access to Liberty...
The South Elkhorn Trail is a short community path in the southern reaches of Lexington, Kentucky. The rail-with-trail skirts the edge of the new housing developments centered on Newbury Way and...
Squires Road Trail is a 1.3 mile multiuse trail on the southeast edge of Lexington, KY. The trail begins on Squires Road and threads through neighborhoods until its terminus at Summerhill Road....
Liberty Park heads north from the west end of the Brighton East Rail Trail in Lexington. Following Liberty Road somewhat, the trail crosses Star Shoot Parkway, where it provides access to Liberty...
The Brighton East Rail Trail was Fayette County's first, opening in 2007. The original 1-mile trail through recent residential development between Bryant Road and Pleasant Ridge Park proved...
Squires Road Trail is a 1.3 mile multiuse trail on the southeast edge of Lexington, KY. The trail begins on Squires Road and threads through neighborhoods until its terminus at Summerhill Road....
Although short in length, the Hope Center Trail provides an important connection between two other trails in Lexington’s northern neighborhoods. The paved, 0.3-mile pathway gets its name from the Hope...
The Coolavin Rail Trail runs for a half mile in northern Lexington's Smithtown neighborhood. The paved pathway begins on a quiet street adjacent to the Transylvania University Athletics Complex and...
The Legacy Trail runs north-south through Lexington among green spaces, neighborhoods and parks. Two highlights of the popular pathway are the Lexington YMCA and Kentucky Horse Park, which features a...
Town Branch Trail in northwest Lexington currently extends between Leestown Road and Alexandria Road, following an old railroad corridor between a subdivision and cultivated fields. Plans call for...
The South Elkhorn Trail is a short community path in the southern reaches of Lexington, Kentucky. The rail-with-trail skirts the edge of the new housing developments centered on Newbury Way and...
Liberty Park heads north from the west end of the Brighton East Rail Trail in Lexington. Following Liberty Road somewhat, the trail crosses Star Shoot Parkway, where it provides access to Liberty...
The Coolavin Rail Trail runs for a half mile in northern Lexington's Smithtown neighborhood. The paved pathway begins on a quiet street adjacent to the Transylvania University Athletics Complex and...
The South Elkhorn Trail is a short community path in the southern reaches of Lexington, Kentucky. The rail-with-trail skirts the edge of the new housing developments centered on Newbury Way and...
The Brighton East Rail Trail was Fayette County's first, opening in 2007. The original 1-mile trail through recent residential development between Bryant Road and Pleasant Ridge Park proved...
Although short in length, the Hope Center Trail provides an important connection between two other trails in Lexington’s northern neighborhoods. The paved, 0.3-mile pathway gets its name from the Hope...
The Legacy Trail runs north-south through Lexington among green spaces, neighborhoods and parks. Two highlights of the popular pathway are the Lexington YMCA and Kentucky Horse Park, which features a...
Town Branch Trail in northwest Lexington currently extends between Leestown Road and Alexandria Road, following an old railroad corridor between a subdivision and cultivated fields. Plans call for...
Squires Road Trail is a 1.3 mile multiuse trail on the southeast edge of Lexington, KY. The trail begins on Squires Road and threads through neighborhoods until its terminus at Summerhill Road....
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
Excellent connector to Brighton East Rail Trail. Limited parking at the school or on the road. Some parking on the Brighton East Trail end point at Walnut Grove Road.
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).
I enjoyed the trail. Can't avoid the road noise, but looking at the country side, creek and whatever else made up for it. It was hillier than I expected, but manageable. Not just having a straight trail was nice also. I read the signs about the jockeys, horses and farms, which were interesting. I do agree that more signs are needed by the water tower area and the southern end to get to Hope Center Trail and Coolavin Trail. (I'll add a review at those sites). I was confused about the mileage. I parked at the YMCA, and went north until it ended at the gate, came back, went on the Hope Center Trail (both ways), the Coolavin Trail and a few blocks on city streets, and finally came back to my car at the YMCA and got a total of 24 miles, whereas the Legacy Trail was supposed to be 12 one way or 24 round trip on its own. I live in Ohio, so not near this trail, otherwise I would ride it more often.
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Map Search
