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 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 Cathy Crocket Memorial Trail occupies the former railroad right-of-way of the CincinnatiĀSouthern Railway that was relocated in the 1950s when Lake Cumberland was formed. The trail begins along US...
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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...
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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...
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 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 Cathy Crocket Memorial Trail occupies the former railroad right-of-way of the CincinnatiĀSouthern Railway that was relocated in the 1950s when Lake Cumberland was formed. The trail begins along US...
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...
The Cathy Crocket Memorial Trail occupies the former railroad right-of-way of the CincinnatiĀSouthern Railway that was relocated in the 1950s when Lake Cumberland was formed. The trail begins along US...
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...
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 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...
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.
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.
The trail was only light used considering it was a Saturday morning. The start for us was just south of the Ky Horse park and was a very nice lot with an air pump. We went on into the Horse park camping ground where the trail ended for some drinks then headed back south.
The trail was clean quiet and meandered in and out of the woods and fields.
It ends abruptly on the North side of Lexington and it is not far to downtown if you want to get on the roads.
Very much enjoyed the trail and would recommend it for a quiet and relaxing ride
I'm new to Lexington and I was surprised to find out that there really is only one truly good and safe route to cycle, which is the Legacy. I came from a state that had many great trails to choose from. so I was a little disappointed that this was the only one that had any real distance to it. This trail is a very good route for an avid cyclist, short but good. Smooth pavement, well kept and very scenic. The hills are challenging which is a bonus to push yourself. It's not an easy breezy ride (flat), so it really is a good workout for your legs. I heard they are to expand this trail in the future and I hope that is true and soon. It not only gives cyclists a great route to open up on, but it also gives families with young kids a safe place to ride to have a nice family outing. For the most part everyone on the trail, joggers, pet walkers and cyclists are polite and courteous to others.
This is a beautiful, well-maintained trail. The total length is approximately 2 miles so it is a little bit short for serious cycling. It is excellent for the not so serious cyclists and children. There is lots of tree cover, which provides a cool place to walk or ride on hot sunny day. The trail is often crowded with people walking, running, biking and even using non-motorized scooters. Most everyone is aware of the various trail users travelling at different speeds and are respectful and friendly. Excellent place for locals to get a little exercise.
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