Coleman-Desha Plantation

The Confederate Monument in Cynthiana is located on the outer edge of Cynthiana, Kentucky in Battle Grove Cemetery. It was the first monument to the Confederate States of America dedicated in the State of Kentucky, and long believed to be the first Confederate memorial anywhere. Due to the 32nd Indiana Monument having been moved from its original location, the Cynthiana monument is the oldest Civil War monument still standing at its original location, where the second Battle of Cynthiana started, in the then-new town cemetery. The Cynthiana Confederate Monument Association, a group of women, spearheaded the movement to build the monument, although the money required to build it came from men. It was built in 1869 by the Muldoon Monument Company of Louisville, Kentucky, at the cost of $2,200. The white marble obelisk stands 22 feet (6.7 m) high on a four square foot limestone base three feet high (25 feet high combined), with a Confederate flag draped atop it. The graves of 47 Confederate veterans who died during the Civil War, many of whom are unknown, and a substantial number of John Hunt Morgan's 2nd Kentucky Cavalry who twice raided the town of Cynthiana during the War, were transferred from another cemetery to encircle the monument. David M. Snyder died in 1896, and per his wishes to be buried with his companions, was placed as part of the circle. The Cynthiana monument set the tone of many of the first Bluegrass monuments in the Confederacy, being reminiscent of death, particularly grave markers. This is best represented by the Confederate Monument of Bowling Green, Confederate Monument at Crab Orchard, Confederate Monument in Georgetown, and the Confederate Monument in Versailles. On the back of the monument is a verse from the Bivouac of the Dead, which six other monuments would also include a verse from. The Cynthiana Democrat said the monument was not just for the local citizenry, but "for every man and every nation, whose children and whose people have shed blood in defense of their Homes, in defense of their country, in defense of Justice and Truth". The dedication ceremony for the monument, held on May 27, 1869, involved a parade, speeches, and food. Colonel W. C. P. Breckinridge gave the dedication speech, highlighting the virtue of the Confederate cause and the bravery of its soldiers. Soon thereafter, his cousin's wife, Mary Cyrene Burch Breckinridge, founded the Ladies Memorial and Monument Association of Lexington. This group raised the funds to create and install the Ladies' Confederate Memorial in the Lexington Cemetery. On July 17, 1997, the Cynthiana monument was one of sixty-two monuments included in the Civil War Monuments of Kentucky MPS.

Spur Gasoline Station, at 201 E. Bridge St. in Cynthiana, Kentucky, was built in 1925. It was listed on the National Register of Historic Places in 1987. It is a one-story 13 by 13 feet (4.0 m × 4.0 m) prefabricated building, 8 feet (2.4 m) high to its eaves, with elements of Classical Revival style.

Monticello of Monticello Heights in Cynthiana, Kentucky was built in 1883. It was listed on the National Register of Historic Places in 1974. It is a mansion which was built around 1883 for Thomas Jefferson Megibben at reported cost of $300,000. It overlooks the town of Cynthiana and was approached by a long curving drive. It was designed by the Cincinnati architectural firm of Samuel Hannaford. The house no longer exists but its carriage house survives.

The Harrison County Courthouse in Cynthiana, Kentucky is a Greek Revival-style courthouse building built in 1851. It was listed on the National Register of Historic Places in 1974. Located at 100 Main Street, it was built and was perhaps designed by John Huddleston. It is a contributing building in the 1982 NRHP-listed Cynthiana Commercial District.

The Church of the Advent, Episcopal in Cynthiana, Kentucky is a historic church at 122 N. Walnut Street. It was built in 1855 and added to the National Register in 1978. It was deemed "architecturally significant as a fine adaptation of the Gothic Revival-a style traditionally deemed appropriate for churches of the Anglican Communion. Its seating capacity of eighty-five is symbolic of the religious fervor and optimism of the parish,-which recorded only eleven communicants and thirty-five Sunday School pupils at the time the cornerstone was laid. The building also attains merit through its association with the Right Reverend Benjamin Bosworth Smith, a pioneer Kentucky clergyman and educator." Its square tower was completed in 1860. It is built of limestone and has a Latin cross plan. The church's website can be found at https://churchoftheadvent.us.

Cynthiana is a home rule-class city in Harrison County, Kentucky, in the United States. The population was 6,402 at the 2010 census. It is the seat of its county.

The Battle of Cynthiana, or more specifically the Second Battle of Cynthiana or the Battle of Kellar's Bridge, included three separate engagements during the American Civil War that were fought on June 11 and 12, 1864, in Harrison County, Kentucky, in and near the town of Cynthiana. This was part of Confederate Brigadier General John H. Morgan's 1864 Raid into Kentucky. The battle ultimately resulted in a victory by Union forces over the raiders and ended Morgan's Last Kentucky Raid in defeat. Morgan's command had previously captured the town in the First Battle of Cynthiana, July 17, 1862. At dawn on June 11, 1864, Brig. Gen. John H. Morgan approached Cynthiana with 1,200 cavalrymen. The town was defended by a small Union force under Colonel Conrad Garis, commanding five companies of the 168th Ohio Infantry and some home guard troops, about 300 men all together. Morgan divided his troops into two columns which approached the town from the south and east, and launched an attack at the covered bridge, driving Garis' forces back towards the Kentucky Central Railroad depot and north along the railroad towards the Rankin House, which Federal troops used as a fortified position. Having no artillery in which to drive the Federals from their positions, the Confederates set fire to the town, destroying thirty-seven buildings and killing some of the Union troops. As the fighting flared in Cynthiana, another Union force, about 500 men of the 171st Ohio Infantry (along with 30 men from the 47th Regiment Kentucky Volunteer Mounted Infantry and 70 men from the 52nd Regiment Kentucky Volunteer Mounted Infantry) under the overall command of Brigadier General Edward Hobson, arrived by train about a mile north of the Cynthiana at Keller's Bridge, the bridge having been burned by a detachment of Morgan's command a few days prior. This force fought portions of Morgan's force for about six hours. Eventually Morgan trapped this new Union force in a meander of the Licking River. All together, Morgan had about 1,300 Union prisoners of war camping with him overnight in line of battle. The 171st Ohio Infantry was paroled the next day. This engagement, Morgan's last victory, was known as the Battle of Keller's Bridge [bridge named for Abraham Keller, not spelled "Kellar"]. With little ammunition, Morgan recklessly decided to stay and fight an expected larger Union force. Brigadier General Stephen G. Burbridge with 2,400 men, a combined force of Ohio, Kentucky, and Michigan mounted infantry and cavalry, along with a section of artillery, attacked Morgan at dawn on June 12, this action taking place on the hills east of town. The Union forces drove the Rebels back, causing them to flee into Cynthiana, where many were captured or killed. General Morgan and many of his officers escaped. Combined casualties in the separate Union forces were 1,092 men, while Morgan is estimated to have lost about 1,000 men, although no firm records exist. Cynthiana demonstrated that Union numbers and mobility were starting to take their toll; Confederate cavalry and partisans could no longer raid with impunity.

The John Lair House near Shawhan, Kentucky was listed on the National Register of Historic Places in 1983. The listing included three contributing buildings. It is a three-bay two-story hall-parlor plan dry stone house.

Lair is an unincorporated community in Harrison County, Kentucky, United States. Lair is located on U.S. Route 27, 3.4 miles (5.5 km) south of Cynthiana.

The John Hinkson House in Harrison County, Kentucky near Shawhan, dates from c.1790. It was listed on the National Register of Historic Places in 1983. The house is a three-bay two-story dry stone house hall-parlor plan house. It was built by John Hickson, a Revolutionary War soldier and famous early settler, who led the first group of white men up the Licking River to settle in this area. The listing included four contributing buildings and a contributing structure. It has also been known as the Old Ammerman Place.

Townsend Creek is a stream in Bourbon and Harrison counties, Kentucky, in the United States. It is a tributary of the South Fork Licking River. It was named for John Townsend, who settled near the creek in 1775.

Shawhan is an unincorporated community in Bourbon County, Kentucky, United States. Shawhan is located along Kentucky Route 1893 6.4 miles (10.3 km) north of Paris. Shawhan was a station on the Kentucky Central Railroad.