House on KY 1492

The Bates House in Trimble County, Kentucky near Bedford was listed on the National Register of Historic Places in 1984. It is a one-and-a-half-story brick Federal-style house, with Flemish bond on its front facade and common bond elsewhere. It was deemed notable as " one of the outstanding examples of the federal style in Trimble County. As one of three federal style hall-parlor dwellings included in the Historic Resources of Trimble County, the Bates House, the Bird House and Tm-55 represent the best illustrations of this particular style in Trimble County. The dwelling is historically significant in the early development of the county, and a significant cultural resource. Although in a neglected state today, the Bates House displays excellent craftsmanship and design, and reflects admirable architectural qualities of the Federal style as is evident by the flemish bond facade, period embellishments of the exterior facade bays and outstanding interior detailing."

Hunter's Bottom Historic District is a 2,810 acres (11.4 km2) historic district in Kentucky's Carroll and Trimble counties, spanning the area known as Hunter's Bottom. It was listed on the National Register of Historic Places in 1976. The listing included 21 contributing buildings and a contributing site. Hunter's Bottom runs seven miles along the Ohio River, with the river forming the north boundary, and with the base of hills forming the south boundary. The district stops on the east at Locust Creek in Carroll County, and on the west at Canip Creek in Trimble County.

Cedar Cliffs Park is a park in Jefferson County, Indiana, on the northern shore of the Ohio River, overlooking Trimble County, Kentucky. The park is on the north side Indiana State Road 56 just east of the town of Madison, Indiana.

Milton is a home rule-class city along the south bank of the Ohio River in Trimble County, Kentucky, United States. The population was 597 at the time of the 2020 census, making it the largest city in Trimble County. The Milton-Madison Bridge connects it to Madison, Indiana, and is the only road link between the two states for 40 miles (64 km) in either direction. It was part of the setting for the 1958 film Some Came Running starring Frank Sinatra, Dean Martin, and Shirley MacLaine.

The Milton Masonic Lodge and County General Store in Milton, Kentucky was listed on the National Register of Historic Places in 1983. It is a two-story three-bay brick building with a hipped roof, built in the last quarter of the 19th century for the Masonic Lodges in Milton, with first-floor commercial space. It continued to serve as a lodge hall through the date of its NRHP listing.

Ginn's Furniture Store is a historic commercial building in downtown Milton, Kentucky, United States. Built in the late nineteenth century, it has endured several major floods.

The Milton–Madison Bridge (also known as the Harrison Street Bridge) is a continuous truss bridge that carries U.S. Route 421 over the Ohio River between Milton, Kentucky and Madison, Indiana.

St. Michael the Archangel Church is a former Catholic church in Madison, Jefferson County, Indiana, United States. It was closely associated with Shawe Memorial High School which was named after the founder of this church.

Jefferson County Jail, also known as Jefferson County Jail and Sheriffs House, is a historic jail and residence located at Madison, Jefferson County, Indiana. It was built between 1848 and 1850, and is a two-story, rectangular Greek Revival style masonry building. The building consists of two blocks: a residential section in front and jail block at the rear. A kitchen wing was added in 1859. It features a classic pedimented gable temple front with a recessed entrance and pilasters.: 2–3  It was listed on the National Register of Historic Places in 1973. It is located in the Madison Historic District.

Locust is an unincorporated community located in Carroll County, Kentucky, United States. Its post office is closed. Locust is located west of the Little Kentucky River and southeast of Hunter's Bottom. The Hopewell Methodist Church was built in 1842 on land donated by Henry Wise. The Locust Baptist Church was constructed in 1866 along Locust Creek. It served as the commercial, religious, and educational center of northwest Carroll County from 1880 to 1940. The Locust General Store was originally at the forks of Locust Creek and flooded regularly. By the time owner James Mosgrove died in 1882, the store was purchased by John and W. Harvey Conway and expanded its agricultural supplies. In 1902, the store was moved to higher ground and a creamery and icehouse were added. The Locust School was built in 1895; the community also supported a high school, which closed in 1938. During the Great Depression, many farmers in Locust went bankrupt due to the failure of the tobacco market. Locust has always been a small community, with a peak population of about 60.

Monitor is an unincorporated community located in Trimble County, Kentucky, United States. Monitor was once a vibrant community, with a school, post office, general store, and black smith in the early 1900s.

Lemuel Allen Farm is a historic home and farm located in Madison Township, Jefferson County, Indiana. The farmhouse was built in 1877, and is a 1+1⁄2-story, central passage plan, vernacular Italianate style brick dwelling. It features a side-gabled roof sheathed in slate shingles with triple-embedded and diamond patterns in red on either side of the front-gable on the façade. Also on the property are the contributing privy and large, transverse-frame basement barn, built around 1877, and a silo, the workshop, the granary, the garage, the feed shed, and a tool shed, all dated to the 1920s. It was listed on the National Register of Historic Places in 2016.