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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.
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.