Find the top rated trails in Winchester, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.
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The Legacy Trail runs north and south through Lexington among green spaces, neighborhoods and parks. The trail joins Kentucky Horse Park and the Lexington YMCA but there are plans to extend it south...
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Town Branch Trail in Lexington currently extends between Leestown Road and Alexandria Road, following an old railroad corridor between a subdivision and cultivated fields. Plans call for extending the...
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...
Town Branch Trail in Lexington currently extends between Leestown Road and Alexandria Road, following an old railroad corridor between a subdivision and cultivated fields. Plans call for extending the...
The Legacy Trail runs north and south through Lexington among green spaces, neighborhoods and parks. The trail joins Kentucky Horse Park and the Lexington YMCA but there are plans to extend it south...
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...
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 Legacy Trail runs north and south through Lexington among green spaces, neighborhoods and parks. The trail joins Kentucky Horse Park and the Lexington YMCA but there are plans to extend it south...
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...
Town Branch Trail in Lexington currently extends between Leestown Road and Alexandria Road, following an old railroad corridor between a subdivision and cultivated fields. Plans call for extending the...
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.
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)
This really is a nice trail. It is obvious this was not a cheap trail to build. It is fully paved and there are several steel bridges that are bike path only. I will enjoy it again next time I am down there. Also, if you enjoy MTB check out Veteran's Park. That is a really funny and flowy MTB trail.
..according the mile markers that show ~10 @the ky horse park end and ~2 @ the ymca end. not a rail trail either; lots of zigs and zags and rolling hills through rural suburbia, that provided a great workout in a hurry. very smooth surface in great condition had my gear higher for such a breezy sunday in mid-may. light crowd for such nice weather too.
A little chilly today but beautiful out on Legacy. My first visit - I'll be back! Well maintained path. Sculpture and artwork along the path gave it some added interest!
A well maintained trail winding through a beautiful landscape. There was evidence that a lot of money was spent on this trail. It is well paved, the staging area on the north end has ample parking and a maintenance station, and there are murals at regular intervals that are worth stopping to check out.
Everyone on the trail was friendly. Every person I passed said hello.
Hopefully this trail will be connected with more rides in the future.
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