Winchester is not all bad, as most would think. Most people simply have forgotten the wonders that are in it. For example, Lower Howards creek and Nature preserve boasts a calm retreat for anyone looking to get away from the daily succubus feeling that curses Winchester residents. The hiking trail is 2 miles long (and if you go off the hiking trail there is a secret 2 story tall waterfall and decent swimming hole called "Halls Falls" though if caught in this area it carries a $1,000 fine per day per person penalty) and there is plenty of parking behind Hall's On The River
The Holder Hiking trail is not only a good workout, it's relaxing, educational, and features plant species found nowhere else in the region as well as historical artifacts like the Holder House built back in the pioneer days. Captain John Holder rescued Daniel Boone's daughters on the battle of Howard's creek from the Native Americans who had kidnapped them during an afternoon kayaking down the Kentucky River. The trail features the remains of his stone house, a once prominent house to the man who industrialized the river and thus bringing trade and goods to the town of Winchester Kentucky.
Hall's Falls is on private reserve property (though poorly marked by signs I did not know this at the time as a trail leads right to the place.) It is truly a sight to behold. A perfect solitude for those looking to experience nature without the drive to Natural Bridge right in Winchester's very own back yard.
Some animals to see are different species of trout, bass, catfish, as well as evening bats, fox, coyote, deer, black bear, river otter, and bobcat. I recommend packing a light snack and plenty of water as the hike is more difficult than your average natural bridge, and when its spring the high flood waters make the creek crossing difficult.
Go explore your town Winchester.. It's not all that bad.