Kentucky Route 1958 (Bypass Road) is an outer loop around the town.

Kentucky Route 627 (Boonesborough Road) leads towards Richmond, 21 miles (34 km) to the south and Paris to the north.

Interstate 64 passes through the northern part of the city, with access from exits 94 and 96.

The Mountain Parkway turns off I-64 just northeast of Winchester and leads 75 miles (121 km) east to Salyersville.

[4] The climate in this area is characterized by hot, humid summers and generally mild to cool winters.

28.5% of all households were made up of individuals, and 12.6% had someone living alone who was 65 years of age or older.

[11] Winchester is home to the Beer Cheese Festival held annually in June.

Beer Cheese was developed in Clark County near Winchester in the 1940s.

After Southeastern Christian College folded in 1979, the campus was preserved as a public park.

Today, Clark County is home to the Winchester Campus of Bluegrass Community and Technical College.