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 Brighton East Rail Trail . 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.
Couldn’t have asked for a more beautiful day and temperature. The trail was really nice. We parked at the spot near the horse park and road toward the end point near the horse park. The horses were still grazing in the morning prior to the opening of the park. We road to Newtown Pike and had lunch at the Jimmy John’s. We decided not to continue into town along the trail. Instead we headed back to the end point near the horse park again. All together we rode 19.8 miles and were blessed with a nice breeze. So glad we made the drive from Louisville. A nice change and beautiful landscapes.
I started at the trail “ending” downtown - but there was no parking, no trailhead, no facilities, and no sign to identify the trail. Strange. I parked at the Catholic Church down the street. I was told I could park at the YMCA, but how do out of town people know this. Then, it was difficult to follow the trail at crossings - very few signs or road markings. The trail is nice, good surface, and beautiful scenery toward the north end. But then it ends at a farm gate - no parking, no facilities, no trailhead, and no signs. Strange. Lexington needs to develop it more! a nice trail.
My son and I hiked the trail for one of his Scout merit badges. A well maintained trail. Most cyclists were courteous about saying “passing on left”. There is water and picnic tables and restrooms at mile marker 5.6. There are also port-a-pots in a few other areas along the way. Our route took us from the Horse Park to the end of the trail and back. We did take a couple of the shorter trails off the main trail. Overall a great experience.
Wife, special needs adult son & I rode about 2/3rds of the Legacy Trail on 7/25/2024. We had been in town this week visiting family, who had previously mentioned this bike trail, so I was looking forward to experiencing it. We started at the North end, noontime, with the July heat making itself known. The ride was overall pleasant, despite a considerable amount of time spent in close proximity to I64/I75. The only issue we experienced was losing our way (due to inadequate signage) near Coldstream Park. We ended up at an apparent dead end at Aristides Drive, near the Embassy Suites & Marriott & it took about 20 minutes of wrangling, looking at maps on our phones & asking locals how to get back on the main path to get on our way. I was looking forward to completing the entire trail, but the detour and last portion along Citation Drive in the afternoon July heat sapped the remaining commitment we had in finishing. We were able to get a tasty lunch at Jimmy John's and after this break, we were able to do the return trip with no issues. It appears that south to north is more downhill, making it easier. Will definitely ride again next time back in the area. Thanks for a good time!!
Well paved trail. Rode from YMCA to the end and back. About 24 miles total. We had a good ride with beautiful scenery. Some hills but not too bad. We did hear the traffic noise 60-70% of the time.
I ran this trail in March 2024. The review that has been submitted stated that the trail was short and flat. It is short, but it is not flat. The trail legend shows it's split in to three legs, but a person could absolutely do the whole stretch without any issue. There is little to no traffic and even though you do cross a couple of roads, the cars were kind enough to let me run through. There is a slow steep hill through Berry Park and then the rest of the path runs behind a neighborhood of houses. I parked in the "middle" of the three trails at the above-mentioned park and ran southwest first and this was a steady up and down path. It looks as though it has just been repaired as there were still signs of freshly planted grass and straw along the path. However, sadly, there are sinking holes already in the path and even a huge crater in part of it. I then did a loop, returning to the park and then up the northeastern part of the trail. This runs through a cul-de-sac and is an easy road run until the trail picks up again just cross Alumni Drive. The northern part of the trail is mostly shaded and wide with a nice creek running through. I felt safe and the trail seemed to be clear of trash. Not sure I would run this again if I were to return to the area just based on the hills alone. I was just in the area for an overnight stay and needed to fit in a quick 5K before a long car ride home.
I’m in Lexington for business - whenever I’m in a new city - I try to checkout the bike trail. The Legacy Trail did not disappoint- I’m from Central Ohio and our trails are pancake flat - the Legacy Trail has enough elevation to get the heart rate up - but nothing the novice cyclist couldn’t handle. I enjoyed taking in the history in the trail and most importantly- I felt very safe as a solo female rider from out of town. The trail was full of friendly cyclists!
We found ourselves on this trail thinking we were near the end of the legacy trail. There are nice bike lanes marked in green. We turned around due to the amount of broken glass on them . Found a beautiful fox mural on one of the buildings.
Ok there are some hills but all good. Nice maintained smooth. I approves. Hit Boonedogs afterwards and it was yummy.
We did an evening 8 mile ride (out n back). Very few people, birds singing, farm fields and I-75...but it was still perfect. Well maintained, easy access.
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