Boonesboro Trail Senior Living Share: Medical Boonesboro Trail Senior Living Visit Website 2101 Old Boonesboro Rd. Winchester, KY 40391 (859) 236-9644 About Map About New Senior Living Community in Winchester that offers Personal Care and Memory Care apartments. We offer free monthly Dementia Support Group meetings and senior activities/meals. What's Nearby? Distance: 5 10 15 20 25 50 mi.