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 19 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.
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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...
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 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...
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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...
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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 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...
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....
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 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 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...
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....
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...
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 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...
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 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....
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...
I 'm not really sure that this this should be listed as a trail in its own right. This is really just an extension of the existing Legacy Trail. The signage along the trail actually designates it as the Legacy Trail. However, that should not be taken as a complaint. This portion represents another step toward bringing the Legacy Trail into downtown Lexington. I am hopeful that the other extensions will be coming soon.
This trail appears to be a good resource for the community. It provides (1) a safe place for children to ride their bikes separated from automobile traffic, (2) a place for those in the neighborhood to walk their dogs, and (3) a place for a leisurely stroll. It's too short for adult cycling or serious runners. If I lived in the neighborhood, I might use it often, but it is not something that anyone would travel a great distance to use. There is no public parking or trailhead. There are no magnificent views, unless you enjoy looking at power lines.
I live an hour away from Lexington in Louisville (which has its own awesome trail at the Parklands if you're in KY anyway), but I drive to Lexington 2-3 times a month just to enjoy the beauty, serenity and pristine trail on the Legacy Trail. It recently has been extended another three miles past the Kentucky Horse park, making for a nice 25 mile round trip from near the YMCA downtown. The rolling hills, restrooms in the middle and lots of horse country, streams, bridges and well maintained paved trails make this is a great ride!! Go for it
Rode this trail on 30 Sep as part of the BourbonCountryBurn bike tour. Rode from KY Horse Park Campground to downtown Lexington. Trail is very well maintained. Has plenty of information markers along it about the surrounding area and it’s history. Takes you to many old restaurants in the Lexington area.
This is a nice little trail slightly over two miles in length running from Masterston Station Park to Alexandria Drive. It seems to be a decent place to be enjoyed by those who live in the neighborhoods to which it is connected, but, at this point, isn't really useful for any other purpose. There are no trailheads or public parking of any kind. There seem to be long term plans to extend the trail along the existing rail corridor toward downtown Lexington, but those plans have been around for a while and very little has materialized. Lexington has been very good at following through with its trail projects. One would have to assume that this one is not very high on the list of priorities.
In April 2017 a friend and I took a break from interstate driving to ride the Legacy Trail into Lexington and back to its north end. The trail is good pavement and well marked. We liked the frequent signs telling the history and ecology of the area. Also, artists painted the trail surface in places, so it was fun to see their work. If you have time, ride into Lexington from the south end of the trail, to see the restored houses and enjoy a cup of coffee.
Passing through Lexington on I-75, we rode the Legacy trail on Sept 21 starting from the KY Horse Park. Ride on a beautifully constructed and well maintained paved surface along horse farms in the north, gradually becoming more urban as you move south. Very little shade for a hot day, and some sections paralleling noisy I-75, but with many picturesque open vistas. We encountered one short paved detour around a water construction project which was easy to navigate. Near the YMCA at the south end there is a 2.0 Mile trail marker, but the trail apparently ends there for now (it would be nice to add signage indicating the trail end). At the north end, the trail has been recently extended to the NW corner of the Horse Park, but that section is along I-75, even though the view East over the horse pastures is great. The Horse Park is also beautifully maintained and landscaped and worth exploring while there. Convenient campground with showers are available in the Horse Park Campground just East of the Horse Park. This trail is a great break from interstate driving.
Smooth, well maintained, beautiful scenery. A great ride.
This is a clean, well maintained and safe trail. There is a lot of shade to keep cool. It's very frequented, but not crowded. I can't wait until they extend it further.
I just started riding my bicycle again a few months ago and finally decided to ride the legacy trail. I have enjoyed this trail immensely. The scenery is great and the trail is well maintained. I do wish there were a water fountain or two along this trail, however I suppose one can carry their own water with them. I have made this trail a staple to my weekly work outs. (At least weather permitting)
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