Gaineswood is a plantation house in Demopolis, Alabama, United States. The house was completed on the eve of the American Civil War after a construction period of almost twenty years. It is the grandest plantation house ever built in Marengo County and is one of the most significant remaining examples of Greek Revival architecture in Alabama. The house and grounds are currently operated by the Alabama Historical Commission as a historic house museum.

Gaineswood was designed and built by General Nathan Bryan Whitfield, beginning in 1843 as an open-hall log dwelling. Whitfield was a cotton planter and had moved from North Carolina to Marengo County, Alabama in 1834. In 1842 Whitfield bought the 480-acre (1.9 km 2) property from George Strother Gaines, younger brother of Edmund P. Gaines. The grounds had been the site of a notable historic event while owned by George Strother Gaines. When Gaines was serving as the Choctaw Indian Agent he is said to have met with the famous chief of the Choctaw Nation, Pushmataha, under an old post oak tree on what would become the Gaineswood estate to work out the terms of the treaty which would lead to the Choctaw Indian removal. This tree became known as the Pushmataha Oak. Whitfield named the estate Marlmont in 1843 and then in 1856 renamed it Gaineswood in honor of Gaines. Whitfield family tradition maintained that Gaines' original log house is the nucleus around which Gaineswood was built and was located at the present location of the south entrance hall and office. Gen. Whitfield sold the house to his son, Dr. Bryan Watkins Whitfield, in 1861. This second generation of Whitfields maintained Gaineswood as a residence, along with the nearby Foscue-Whitfield House, which Mary Foscue Whitfield inherited in 1861 upon her father's death. The Whitfield family sold Gaineswood in 1923 and it was acquired by the state of Alabama in 1966 from Dr. J.D. McLeod.

Gaineswood was completed in its current Greek Revival form in 1861. It is considered to be " Alabama's finest neoclassical house" and one of America's most unusual neoclassical mansions. Gaineswood is one of the few Greek Revival homes in the United States that uses all three of the ancient Greek architectural orders and features an asymmetrical layout. Whitfield is known to have designed most of the house from pattern books by James Stuart, Minard Lafever, Nicholas Revett and others. Much of the work on the house was executed by highly skilled artisan slaves.

The interior features decorative plasterwork throughout the main floor. The library and the dining room both feature elaborate domed ceilings with central skylights. The hallway features fluted Ionic columns in the main entrance hall with reception rooms to either side, one for each sex. The master's bedroom also features two fluted Ionic columns supporting a cornice that visually divides the room into bedroom and sitting room. The mistress' bedroom features a large floor to ceiling semicircular bay with curved windows and is fronted by two fluted Corinthian columns. Doors to either side of the bay provide access to the semicircular porch outside. The ballroom features four fluted Corinthian columns and twenty-four fluted Corinthian pilasters, vis-à-vis mirrors, an elaborate plaster cornice, and a coffered ceiling. The second floor is much simpler in decor and contains a boudoir, a nursery, and four large bedrooms.

The exterior has a decorative stucco over brick treatment intended to look like ashlar blocks. The exterior features the use of eighteen fluted Doric columns and fourteen plain square pillars to support the three porches, the main portico and the porte-cochere. Parterres with low balustrades and including marble statuary are featured off the main portico and south porch. The estate continues to feature a cook's house, a garden pavilion with eight fluted Corinthian columns, a monumental entrance gate, and a matching gatehouse that date to the antebellum period.

Whitfield canal
Whitfield had this drainage canal dug by hand by his slaves between 1845 and 1863 to prevent water from overflowing and flooding the plantation. The rainfall on a large section of the Gaineswood estate originally had to follow a 17-mile (27 km) course to reach the Tombigbee River. The canal is about one mile (1.6 km) long and ranges to more than 30 feet (9.1 m) deep through the underlying chalk, it quickly diverts the surface water into the river at Demopolis.

Gaineswood is on the National Register of Historic Places and was designated a National Historic Landmark in 1973. The estate is owned by the state of Alabama and is administered by the Alabama Historical Commission. Much of the original family furniture and some statuary has been returned to the house by the Whitfield family. Severe moisture damage to the ceiling and dome in the dining room is being addressed by a Save America's Treasures grant.

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