The papers open with a single item of Henry Hill (1743-1815), a planter and Continental Army officer who was progenitor of the Culpeper Hills. He built "Millwood" on a plantation just across the county line in Madison near presently-day Novum. The home figured prominently in the affairs of his son A. P. Hill.

Captain Ambrose Powell Hill (1785-1858), uncle of the Confederate general of the same name, served as a justice of the peace, sheriff and legislator for Culpeper County. He lived primarily at Culpeper Court House, but also spent time at the home he inherited from his father, "Millwood."

Captain Hill's correspondence reflects his various interests as a planter and local official. It includes letters from Congressman John Strode Barbour and Governor William Smith. In 1844 Hill was appointed one of the commissioners of the Culpeper County Court to consider the construction of a bridge spanning the Rapidan River between Culpeper and Orange counties. He maintained records as superintendent of the building of Germanna Bridge, including orders of the county court, specifications, a bond of the contractor, William T. J. Richards (in the hand of William Green), and accounts. Hill also served as president of the Thornton's Gap Turnpike Company, 1850-1854. His records include correspondence and reports, minutes, a memorial to the Virginia Board of Public Works, specifications for the turnpike and Hazel River Bridge in Culpeper County, an account book and loose accounts, and a deed (copy) from James Barbour.

As sheriff and in his private capacity, A. P. Hill also acted as executor of a number of estates in Culpeper County. His records primarily include correspondence, accounts and inventories. One of the estates, that of Mrs. Elizabeth Fry (d. 1844), made significant bequests to Baptist organizations and institutions. Hill's personal miscellany includes as well records of his activities as a member of Mount Pony (later Culpeper) Baptist Church. Estate materials, kept by his son and administrator, William A. Hill, include a conveyance of "Millwood," division of slaves, and records of two lawsuits concerning the estate settlement.

John Booton (1786-1845) was a son of William Booton and Frances Hill, a sister of Henry Hill (1743-1815). Booton lived at "chestnut Grove" in Madison County and his family attended Liberty Baptist Church, just across the line in Greene County. He pursued an active, if erratic, career in local affairs. His correspondence includes letters of Madison clerk Belfield Cave (concerning a contested election in 1841; see below) and lawyer William Green. A large group of loose accounts covers the purchase and sale of tobacco and wheat, subscriptions to Baptist publications, and, like almost all groups of accounts in this collection, local taxation. John Booton and his broth Sinclair also had a financial interest in John S. Beazley & Co., merchants in Rapid Ann (now Wolftown), Va.

As well as planting, Booton acted as deputy sheriff in Madison under a succession of sheriffs, including William Booton and Robert Thomas. His tenure covered the years 1815-1843, during part of which time his brother Sinclair also served as deputy sheriff. Booton's records include auditor's receipts; receipts from the Madison county commissioner of the revenue; Sheriff's receipts (including fees for "farmage" - the leasing of the office of sheriff to a deputy in return for a portion of collected fees); executives of judgments, orders and writs issued by the county court or individual justices; a bond of the jailor concerning the county jail; fee book, 1828; and records as administrator of estates in Madison County (primarily accounts and inventories), committed to the sheriffs by the county court.

Records of land purchased or sold by John Booton in Madison and Orange counties include deeds, agreements, receipts, surveys and plats. Other materials include judgments issued in 1837 as a justice of the peace, and records as clerk of the lst and 2nd Battalions of the 82nd Infantry Regiment of Virginia Militia (primarily fines for failing to attend muster) Booton was twice elected to the House of Delegates for Madison County (1839 and 1840) and both times his election was successfully contested by opponent Robert Alexander Banks. The latter investigation created a tense situation in the county (see Belfield Cave letters; House Journal, 1840-1841, Doc. No. 45, and election materials in this collection).

John Booton acted as trustee for his cousin Henry Hill (1782-1846) and brother-in-law William Henry Hill (1803-1880), and as administrator of the estate of his brother Sinclair (1797-1839). Among his miscellaneous records are slave materials and 1830 agreement concerning a copper mine in Orange County. Estate materials, kept by executors Edwin Booton and William A. Hill, include inventories and appraisals, loose accounts, sales and tax records, an account book covering the guardianship of Ann Powell Hill Booton (b. 1827), and records of the division of "Chestnut Grove" after the death of Booton's wife.

Captain A. P. Hill's son, William Alexander Hill (1817-1890), was both a physician and a Baptist minister. He built and lived at "Glendalough" near Locust Dale in Madison County. His correspondence consists primarily of family letters, including a number from his sons while they served in the Confederate Army and to his daughter describing military operations in and around Culpeper and Madison counties. Other correspondents include Governor William Smith and General James Gaven Field, later attorney-general of Virginia; additional subjects include financial matters and Baptist church affairs.

Dr. Hill was educated at the University of Pennsylvania in Philadelphia. His records include class cards issued to attend medial lectures. Hill served as executor of Oliver B. Jenks, a New Hampshire-born physician who practiced in Madison and married one of Hill's Twyman cousins. The records include an account book, loose accounts, 1858-1875 (primarily for medical services rendered), receipts and bonds. Hill also served as administrator of several other estates in Madison, including that of Baptist benefactor Daniel J. Smoot. Miscellaneous items include materials concerning Hill's pastorates at Liberty Church in Greene County and Antioch Church, a black congregation at Culpeper Court House, as well as records as first superintendent of schools in Madison and Greene counties. Dr. Hill's wife, Judith Frances (Booton) Hill (1822- 1909), was a daughter of John Booton. Her correspondence consists primarily of family letters, though a number concern the death of William A. Hill. Thomas Hill (b. 1810?) was a brother of William A. Hill. A few items of financial interest comprise his papers in Box 9.

Edwin Booton (b. 1820) and John Booton (b. 1825) both moved to Greene County. Some of their accounts were generated as agents for their month, Ann Powell (hill) Booton. Their unmarried sister, Ann Powell Hill Booton (b. 1827) lived at "Chestnut Grove" and later at "Glendalough". Her papers consist primarily of family correspondence (especially with nephew Hugh Hodge Hill), guardian's accounts kept by William A. Hill, 1847-1862, and loose financial records.

John Booton Hill (1841-1913), son of Dr. William A. Hill, worked for his uncle Henry Hill (1816-1866) as a paymaster for the U. S. Army preceding the Civil War. In 1861 he returned to Madison as Captain of Co. C of the 82nd Regiment of Militia. He was soon transferred to Richmond, again to assist his uncle in creating the paymaster department for Virginia State Forces and later for the Confederate Army. In 1864 he rose to the rank of Major and was assigned to Anderson's Corps of the Army of Norther Virginia at the Siege of Petersburg. After the War he worked as assistant superintendent of the Richmond Water Works and as treasurer of the E. B. Taylor Co., importers, and was active in First Baptist Church.

Hill's papers include letters, mostly written to his sister Anna while in Confederate service (see also his parents' correspondence); reminiscences of service; obituary notices and memorials; and a few items of his wife, Virginia Byrd (Hudgins) Hill (1842-1925), including notes on the Hudgins family.

Hill's brother William Powell Hill (1844-1929) also served in the Quartermaster's Department of the Confederate Army and later in Co. C of the 4th Virginia Cavalry Regiment. After the War he engaged in lumber manufacturing in Orange County and handled real estate in Culpeper County. Letters to his sister Anna during his Confederate service chiefly comprise his correspondence (see also his parents' correspondence), while two commonplace books concern agricultural labor and activity and a diary of a trip from "Glendalough" to Luray, Va., presumably in 1867.

Dr. Hugh Hodge Hill (1858-?1937) was named for one of his father's medical professors at the University of Pennsylvania. He attended the same school and then practiced in Madison County and as resident physician at Mountain Lake Hotel in Giles County. Among his papers are reports, essays, and exercises while a student at Locust Dale Academy, Locust Dale, Va. (1873-1876); materials concerning his attempt to secure a post as resident physician at Germantown Hospital, Germantown, Pa., in 1896; and some records of his activity in Mt. Zion Baptist Church, Oakpark, Va.

Youngest of the Hill brothers, Francis Irvin Hill (1860-1946) lived for a time in Greensboro, N. C., as an insurance agent and later a manufacturer's representative, but seems to have returned to "Glendalough" in the 1890s. He kept a diary of farm and local events in early 1899 (entries after March 29 were made by his wife, Zilpha), and his accounts are very sporadic except for the years 1935-1945. Miscellany includes about a half-dozen letters written to Zilpha Hill (Brachin) Hill (d. 1906).

Philip Major (b. 1847) married Dr. William A. Hill's eldest daughter. He was a "professor" at Locust Dale Academy and lived at"Glendalough". His wife Anna Lee (Hill) Major (1847-1935), attended school at the Inglewood Female Academy run by Dr. Charles Quarles at "Inglewood" in Louisa County during the Civil War. Much of her correspondence is with family members, schoolmates, and fellow workers in the Baptist Church. Correspondents include James Gaven Field and Baptist ministers Samuel Cornelius Clopton, Oscar Farish Flippo (with photograph), and William Alexander Street.

Julia Henry Hill (1853?-1888) appears in the correspondence of her parents and older siblings. Among her papers is an agreement with the Locust Dale School District in Madison County to teach at Oak Park School House in 1877, and resolutions of the Mt. Zion Baptist Church Women's Missionary Society.

Albert Hudgins Hill (1866-1933), son of John Booton Hill, attended the University of Richmond and began his teaching career in a local evening school. His correspondence includes letters from William Gordon McCabe. He became principal of Scottsville Elementary and High Schools in 1887. Materials include recommendations, a certificate, and a news clipping. Hill joined the Richmond City public schools in 1889, rising from principal to assistant superintendent in 1904 and superintendent in 1919. Materials, 1909-1933, consist of correspondence, accounts, an abortive nomination as superintendent in 1909, records of attendance at Colombia University, 1911-1914, appointment as superintendent, biographical information, essays, news clippings, and resolutions.

Albert Hill married Cora J. Bransford (1867-1941) of Lynchburg. Along with family correspondence and loose accounts, the collection also contains records of her administration of the estate of her sister, Judith H. (Bransford) Silverhorn; a commonplace book, 1913-1936, including notes of deaths of members of the Beers and Bransford families; and an autograph album kept in Lynchburg, 1881-1893. Mrs. Hill's estate materials consist primarily of sympathy notes and letters written to her daughters, Katharine Byrd (Hill) Smith and Judith Bransford (Hill) Weaver.

The last section of the collection consists of miscellany, including a few items of general correspondence of various other members of the Booton and Hill families, 1866-1905; accounts, 1838-1865; obituary notices; clippings, and an agreement of Governor James Lawson Kemper with Alfred Madison Barbour concerning land in Culpeper County.