Looking for the best trails around Winchester?

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.

Recent Trail Reviews

Legacy Trail (KY)

Safe for a Solo Ridee

September, 2023 by jfloweresq

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!

Hope Center Trail

broken glass on bike lanes

September, 2023 by kerr37938

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.

Legacy Trail (KY)

nice and relaxing

September, 2023 by gary.turner2

Ok there are some hills but all good. Nice maintained smooth. I approves. Hit Boonedogs afterwards and it was yummy.

Accordion

Legacy Trail (KY)

Easy and Beautiful

June, 2023 by jeannemoss

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.

Brighton East Rail Trail

I haven't ridden my bike in 4 years! I looked like I had never been on a bike in my life. ¿ It is a great trail, no dogs chasing you and lots of houses in case you have a heart attack! Seriously, I give it ¿¿¿¿¿

June, 2023 by ko2pelli

I haven't ridden my bike in 4 years! I looked like I had never been on a bike in my life. ¿ It is a great trail, no dogs chasing you and lots of houses in case you have a heart attack! Seriously, I give it ¿¿¿¿¿

Squires Road Trail

Paved multiuser trail is short & flat. While not a destination trail, it is nicely shaded and worth a look if you are in the area.

September, 2022 by traillink user

Paved multiuser trail is short & flat. While not a destination trail, it is nicely shaded and worth a look if you are in the area.

Legacy Trail (KY)

Road from YMCA to the end of the trail by The horse Park was a great Trail to ride needed a few more markers and some places but overall great ride

August, 2022 by meburdchc

Road from YMCA to the end of the trail by The horse Park was a great Trail to ride needed a few more markers and some places but overall great ride

Liberty Park Trail

Excellent connector to Brighton East Rail Trail. Limited parking at the school or on the road. Some parking on the Brighton East Trail end point at Walnut Grove Road.

March, 2022 by kyroadcyclist

Excellent connector to Brighton East Rail Trail. Limited parking at the school or on the road. Some parking on the Brighton East Trail end point at Walnut Grove Road.

Brighton East Rail Trail

Short trail that gives access to the surrounding neighborhoods. Connects to The Liberty Trail at the Man O War end & Walnut Grove Road at the other. Walnut Grove offers access to some nice country road riding

March, 2022 by kyroadcyclist

Short trail that gives access to the surrounding neighborhoods. Connects to The Liberty Trail at the Man O War end & Walnut Grove Road at the other. Walnut Grove offers access to some nice country road riding

Legacy Trail (KY)

One of the best bikeways in the state. Rolling hills to the West, city access to the East.

March, 2022 by kyroadcyclist

One of the best bikeways in the state. Rolling hills to the West, city access to the East.

Brighton East Rail Trail

Great for kids

February, 2022 by jonsmack220

Flat grade, wide path, and shade. Wonderful park about midway with restroom facilities. Amazing overpass to MOW. Exits to restaurants and ice-cream.

Legacy Trail (KY)

Pretty and easy tour through horse country, ag fields & college town

February, 2022 by bikeridesandbreweries

We started at the northern trailhead in an RV park next to the Kentucky Horse Park on I-75, a major thoroughfare. There’s a parking lot across the highway, but the actual start of the trail is marked by an obelisk within the RV park. We headed on a paved path toward the beautiful fields and paddocks of the Horse Park, only to have it end abruptly two miles later. Oops. Start in the parking lot across the highway. Or start in town so your round trip will end at one of the town's most popular taprooms.

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