Mathias Wolf Farm

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.

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.

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.

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.

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.

The Madison Historic District is a historic district located in Madison, Indiana. In 2006, it was named a National Historic Landmark due to its unique Midwestern beauty and architecture scheme. Among the prominent buildings in the district are the Lanier Mansion, one of two buildings separately considered a National Historic Landmark in the district, and the Schofield House, the birthplace of the Grand Lodge of Indiana. In total, it comprises 133 blocks of Madison, Indiana, overlooking the Ohio River in Jefferson County, Indiana. Madison's most prominent days were before 1860. It was a major transportation hub, taking river commerce and shipping it to the inland of Indiana. Once transportation routes changed, Madison faltered until the tourism industry saved it more than a century later. Many of the prominent buildings in the district were built by Madison-native-architect Francis Costigan, who favored the Greek Revival style. Two of these are National Historic Landmarks: the Lanier Mansion, and the Charles L. Shrewsbury House. The Lanier Mansion was the former home of James Lanier, who lent money to governor Oliver P. Morton to run the Indiana state government to circumvent the legislative process between 1862 and 1865. The Shrewsbury-Windle House was built for steamboat captain Charles Shrewsbury, who would later become a mayor of Madison. Costigan, himself, built his home in the district, and it is considered one of the best uses of a narrow lot by modern architects. A thirty-foot parlor is considered the highlight of the House. Also located in the district is the restored 1895 Railroad Depot and the Jefferson County Historical Society museum. When the Madison & Indianapolis Railroad was first built in 1835, Madison was far bigger than the new state capital of Indianapolis. The railroad was constructed by Irish laborers. Broadway Fountain was first displayed at the 1876 Centennial Exposition, and then presented to Madison in 1884. It was manufactured by an iron foundry owned by Adrian Janes, who is also responsible for manufacturing the dome of the U.S. Capitol Building, The fountain was replaced by a reproduction in 1981. Madison was also a major stop on the Underground Railroad, with many homes in the area having once been used for assisting the escape of slaves.

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.

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.

Brooksburg is a town in Milton Township, Jefferson County, Indiana, United States. As of the 2020 census, Brooksburg had a population of 72.

The House on KY 1492, near Milton, Kentucky, was listed on the National Register of Historic Places in 1984. It was built between 1800 and 1820 and was deemed notable as "an outstanding example of the Federal style" in Trimble County. It was described in 1982 as a one-and-a-half-story brick house, with brick laid in Flemish bond. Its facade had four bays including a pedimented entrance pavilion. The house was in deteriorated condition in 1982. It was located off Kentucky Route 1492. The house appears no longer to exist.

Madison Township is one of ten townships in Jefferson County, Indiana, United States. As of the 2020 census, its population was 18,007 (up from 17,415 at 2010) and it contained 8,264 housing units.