Kentucky's 6th congressional district

The Oakwood Estate is a house in Winchester, Kentucky. It was listed on the National Register of Historic Places in 1979 as Alpheus Lewis House. It is a one-story home on a raised basement, with Greek Revival details. The Oakwood house, on the Lewis Estate, has a history that dates from the ante-bellum era. The house is on the banks of Stoner Creek, about some miles off of Wades Mill Rd. At the time the house was built, it was home to Alpheus Lewis Sr., his wife and nine children. He was born in 1799. His father was a veteran of the Revolutionary War and a member of the House of Burgesses and acquired 3,000 acres (12 km2) of land which he eventually divided among his sons. Alpheus built his house, which he later named Oakwood. He created a wine business known as "A. Lewis and Sons". Lewis' son, Alpheus ("Ack") Lewis Jr's time in the Civil War, made Lewis and his home well known in Kentucky. The condition of Oakwood today is deteriorating with major instabilities in the structure. The backyard however may still have a rail fence made completely of stone, a rarity. Behind it are the graves of Alpheus Lewis Sr. and his wife Theodosia.

Mound Hill (also known as the "Nelson Gay Mound") is an archaeological site in the Bluegrass region of the U.S. state of Kentucky. Located north of Winchester in far northern Clark County, the site is part of a group of Indian mounds lining Stoner Creek, although by far the largest of the group. The mound has frequently attracted attention from mapmakers and other surveyors, due to its large size; it was measured at 240 feet (73 m) (circumference) and 20 feet (6.1 m) (height) by an 1884 survey, which pronounced it a "romantic sight" due to its hilltop location between Stoner Creek and Pretty Run. The surveyors suggested that its linear shape with a central depression might have been the result of erosion or of the construction of multiple mounds that were later merged into one. It lies approximately 0.5 miles (0.80 km) west of the rest of the group, which occupies the summit of a narrow ridgeline known as the "Devil's Backbone." Digging at these mounds, which were seemingly related to Mound Hill, produced artifacts such as pottery and a pipe, as well as numerous stone box graves. In 1978, Mound Hill was listed on the National Register of Historic Places. One of several Clark County archaeological sites on the Register, it was deemed to encompass an area of 18 acres (7.3 ha) for preservation purposes. It is believed to have been built by peoples of the Adena culture.

The Gen. Thomas Hart House near Winchester, Kentucky, in Clark County, was built by 1808. It was a work of a John Hill. It was listed on the National Register of Historic Places in 1979.The house has a hipped roof and has Federal details including a fanlight. A Clark County historic resources study asserts that the house's "careful Flemish bond brickwork with gauged jackarches is unsurpassed in Clark County."

The Leeds Theatre is a single-screen movie theater in downtown Winchester, Kentucky. One of Winchester's first movie houses, the theater was purchased by S.D. Lee, president of the Winchester Amusement Company on May 12, 1925, and opened with The Crowded Hour starring BeBe Daniels. It was later named in a contest after its first owner S.D Lee, by rearranging the letters of his name. The theater declined in both attendance and general upkeep, closing its doors in 1986. Shortly after, the Winchester Council for the Arts restored the theater to its original appearance. The theater reopened in 1990 as the "Leeds Center for the Arts" with new equipment, a larger stage, and the original paint color scheme of 1925. The theater remains one of Clark County's timeless treasures today, showing films from the Golden Age of Hollywood and highlighting various musical and drama performances.

The S. P. Kerr Building is a historic building on the northwest corner of North Main Street and West Broadway in Winchester, Kentucky. The building is listed in the National Register of Historic Places as a contributing property in the Winchester Downtown Commercial District. Built in 1889, it is a three-story brick building with stone sills and lintels and a rounded corner entrance flanked by rough-hewn stone columns. The building contains about 32,000 square feet (3,000 m2) of space.The Kerr Building originally housed Eclipse Mills, but in later years it was home to J. J. Newberry's and The Corner Drug Store. By 1999, the building was vacant and in disrepair. As a result of the deterioration, the Bluegrass Trust for Historic Preservation placed the Kerr Building on its "11th Hour" Most Endangered list. In 2001, the building was purchased by Union Properties and Bailey Associates, who began refurbishing the building in August 2002, including repairing water damage, leaks in the roof, and worn storefronts. The renovations took more than three years (it was completed in December 2005) and cost more than $2 million. The building now houses around 18,000 square feet (1,700 m2) of senior living space and 9,000 square feet (840 m2) of commercial space.The wooden rooster on the roof of the building is said to have been placed there as the result of a bet involving the outcome of the 1932 presidential election. The original rooster eventually disappeared, but a replacement was installed during the 2002 renovation.

The Winchester Downtown Commercial District is a 21 acres (8.5 ha) historic district that was listed on the National Register of Historic Places in 1982. It included 114 contributing buildings. It includes both the 1853 Clark County Court House and the 1889 S. P. Kerr Building on the northwest corner of North Main Street and West Broadway. The building contains about 32,000 square feet (3,000 m2) of space.

The Clark County Court House is a Greek Revival courthouse in downtown Winchester, Kentucky, United States. Built in 1853, it is the fourth building on this site, and still houses the Circuit Courtroom and Family Courtroom for the Administrative Office of the Courts.The building was added to the National Register of Historic Places in 1974.It is the centerpiece of the Winchester Downtown Commercial District, also NRHP-listed.

Winchester is a home rule-class city in and the county seat of Clark County, Kentucky, United States. The population was 18,368 at the 2010 census. It is part of the Lexington-Fayette, KY Metropolitan Statistical Area. Winchester is located roughly halfway between Lexington and Mt. Sterling.

The Opera House in Winchester, Kentucky, United States was designed in 1873 by the first Mayor of Winchester, J. D. Simpson. The opera house was a gift from the mayor to Winchester's citizens so they could enjoy performing arts. It hosted off-Broadway and classical concerts. The building fell to industrialization and became rundown from years of neglect. It was bought by Edward and Vanessa Ziembroski in 2003, who renovated the building.

The Owen-Gay Farm in Clark County and Bourbon County in Kentucky was listed on the National Register of Historic Places in 1997. The property included two contributing buildings, nine contributing structures and one contributing site, on 238 acres (96 ha). It is located on Gay Rd. at its junction with Donaldson Rd., at the Clark County-Bourbon County line. The house, built in 1825–1840, and 119 acres (48 ha) is in Clark County; some outbuildings and the other 119 acres (48 ha) are in Bourbon County. It includes: the house (1825–1840) a log house (c. 1817), designated BB-362 and known as Glocca Morra School in the Kentucky Heritage Council's Historic Sites Inventory a meathouse (c. 1825) Ice House ruins (c. 1825) cistern (1915–1920) concrete water tank (c. 1945) hay barn (c. 1900) metal crib (1930–1940) an undefined structure (c. 1900) cattle barn (1910–1920) sheep weigh house (c. 1910) as well as agricultural acreage, fences, cemetery, and the farm's residential area which make up a contributing site.

The William Hickman House located at 31 West Hickman Street, is a brick house in Winchester, the county seat of Clark County, Kentucky. It was listed on the National Register of Historic Places in 1982.Its brick on the west facade is laid in Flemish bond; it is common bond elsewhere.Built by John Couchman in 1814, it was originally intended to be a tavern, but before he opened it, it was bought by local cabinet maker William Hickman. Six generations of Hickmans lived in the house, which remained a residence until it was bought by the Clark County Bank in 1982. In 1990 it was bought by Dykeman & Rosenthal, a law firm in Winchester.

Clark Mansion also known as Holly Rood or the Gov. James A. Clark Mansion, is one of the most historic homes in Clark County, Kentucky. Construction began in 1813 for James Clark who was 13th governor of Kentucky and was finished in 1814. It was built specifically for James and his wife, who named it after her father. Clark Mansion is historically significant for its Federal architecture. It is a single building on less than 1-acre (4,000 m2) of land. It is a two-story brick painted red house with a wide front porch and Ionic columns. It also has a wide entrance and the 2nd story has a Palladian window.Clark Mansion sits away from the road and has a huge front yard. It is located close to Hannah McClure Elementary, Library and College Park. The building was added to the National Register of Historic Places in 1974. As it is owned by the local government, people can tour the house and view its antique furniture. It is often used for formal events including weddings. Clark was buried in a private burial ground in the old Clark home at Winchester, Clark County, Kentucky. A Monument was built in the place where he was buried.