Our Virginia Bed and Breakfast, circa 1930. Note the Ford Model A Sport Coupe.

The History of the Holladay House Bed and Breakfast in Orange, Virginia

The Holladay House Bed and Breakfast in Orange, Virginia has witnessed over 175 years of American history, and is on the nationally-recognized Journey Through Hallowed Ground. Now a Virginia Bed and Breakfast inn, the Holladay House is one of the two oldest standing structures in historic downtown Orange, and is registered with the National Register of Historic Places as part of the Orange Commercial Historic District. At the crossroads of historic Routes 15 and 20 (James Madison Highway and Constitution Highway), the property has seen important figures such as James Madison, Robert E. Lee, J.E.B Stuart, A.P. Hill, and Jefferson Davis pass by its doors. In 1863, the property witnessed Union and Confederate cavalry soldiers skirmishing down Main Street, and a local legend describes how a Confederate solider died on the front steps. One block away, the St. Thomas Episcopal Church became a temporary hospital for wounded soldiers after the battles of Cedar Mountain, Chancellorsville, the Wilderness, and Spotsylvania Court House.

Throughout the last two centuries, the Holladay House has served the citizens of Orange, Virginia as a mercantile store, a residence, a doctor’s office, and a Virginia Bed and Breakfast inn. In the early 20th century, a private schoolhouse for local children was also on the property. Only a handful of proprietors have owned the property, and the Holladay family was its steward for over 100 years. The Holladay House still boasts much of its original woodwork, including floors, mantels, doors and period antiques from the Holladay family.

Dinkle and Rumbough
(1821 to ca. 1851)
In 1799, Paul Verdier purchased the property of William Bell, an 18th century farm that included much of the modern-day Town of Orange. Bell’s Tavern was a part of this property, which Verdier renamed the Orange Hotel. The Orange Hotel stood at the site of what is now the historic Orange Court House, which was constructed in 1859.

Paul Verdier divided the William Bell farm into town lots, creating a town layout that survives largely intact. In 1821, Samuel Dinkle purchased one of these lots on behalf of the Lynchburg-based mercantile firm, Dinkle & Rumbough. By the early 1830s, Dinkle & Rumbough had built a brick structure on the property, which would later be expanded to become the Holladay House Bed and Breakfast.

In 1836 and 1837, the merchants expanded their holdings by purchasing the lots adjacent to and behind the property. Jacob Rumbough was apparently an absentee partner because his name does not appear in the local census records. Samuel Dinkle, however, was a town resident, and presumably lived on the upper floors of the store. Another gentleman named Henry Hiden joined the venture. The 1850 and 1860 censuses also list Hiden as the town postmaster.

Dinkle and Rumbough operated their general store until at least the mid 1840s, and possibly as late as the early 1850s. Court documents show that the mercantile firm was in deep debt, but the county court records are not entirely clear about when the firm ultimately dissolved and sold its property. In 1837, the court executed a lien on the property, placing it in the hands of John Madison Chapman, a local lawyer, and gave the merchants one year to pay their debts. The court permitted Samuel Dinkle, Jacob Rumbough, and Henry Hiden to continue to occupy the property until the debts were settled, but available records do not clearly indicate whether or not they lost the property at that time. Five years later, in 1842, Dinkle and Rumbough’s personal property included a “stock of dry goods, groceries, hardware, etc. including hats,” suggesting that they were still in business at that time. A mercantile and professional directory published in 1851 lists “Samuel Dinkle, and hatter” in Orange as “General Dealers in Dry Goods, Groceries, Hardware, etc.” Interesting, the same directory indicates that J.W. and S.D. Rumbough were also selling hats, caps, and shoes in Lynchburg at that time. The 1850 Federal census shows Samuel Dinkle as a merchant in Orange, but he was not living at the property that is now the Holladay House. So, the historical waters are muddy regarding the precise date when the property ceased operations as a general store, and passed to the next owner. The store was likely operating through the mid 1840s, and possibly as late as the early 1850s. Additional research is required to uncover the precise date.

The Chapman Family
(mid-1840s to 1883)
As a result of Dinkle and Rumbough’s financial troubles, John Madison Chapman (1810-1879) acquired the property through a series of liens and deeds. The exact date when he began occupying the property is unclear in the records, but his occupancy began sometime after 1844.

The Chapman family was a prominent family in Orange. John Madison Chapman’s father, Reynolds Chapman, was the clerk of the Orange County court for much of the nineteenth century, and his mother, Rebecca, was the daughter of President James Madison’s younger brother, William Madison (making John Madison Chapman the grand-nephew of President James Madison).

According to deeds for neighboring properties, the house had become affectionately known as “Our House” by 1867. John Madison Chapman was a well-connected lawyer in town, and presumably operated his practice from his newly acquired house on Main Street. In 1855, he was a trustee for the town’s incorporation, although the town was not incorporated until 1872. From 1869 to 1870, Chapman was a presiding justice for the court, and in October 1878, he was a part of the committee to greet President Rutherford B. Hayes. From 1874 until 1879, Chapman served as Town Mayor.

Prominent though he was, John Madison Chapman over-extended his finances. By 1876, he was engulfed in debts and his personal property was in jeopardy. Alfred Thompson, of the mercantile firm Thompson and Snead, filed a chancery suit against Chapman that continued for years after Chapman’s death in 1879. Thompson died in 1883, but the suit continued to wind its way through the court system until 1896—20 years after it began! The court forced Chapman’s wife, Susan, to sell all of her property (including their house on Main Street), and she relocated south of town.

The McDonald Family and the Methodist Parsonage
(1883 to 1899)
As a result of this chancery suit, John McDonald acquired the Chapman family’s Main Street property in 1883, and gave the title to his wife, Elizabeth. Thirteen years later, in 1896, Elizabeth sold a portion of land on the west side of the lot to the trustees of the Methodist Episcopal Church, on which they intended to construct a parsonage. The McDonalds continued to own the Chapman’s former home until 1899.

The Holladay Family
(1899 to 2000)
Dr. Lewis Holladay (1868-1946) purchased the property in 1899, and it is he and his progeny that are the home’s namesake. Born on Christmas Day, 1868, Dr. Lewis Holladay was an accomplished physician, and ran his medical practice in Orange until his death in 1946. The Holladay family is an ancient and prolific Virginia family with roots reaching as far back as the early eighteenth century in Essex County. The Holladay family had a lengthy tradition of service in professional fields, such as lawyers, physicians, and dentists. Lewis’s grandfather, Dr. Lewis Littlepage Holladay (1803-1869), had attended the College of William and Mary and was also a physician. He lived near Rapidan, Virginia, on a farm called “Dunlora.” Lewis Holladay’s father, Henry Thompson Holladay, owned land and a mill near Rapidan, and it was on his farm that Dr. Lewis Holladay (1868-1946) was born.

Dr. Lewis Holladay (1868-1946) married Sally Helen Price in 1892, and moved to Orange after purchasing the McDonald’s house in 1899. At that time, only the brick portion of the house existed, and the Holladays made several additions to the building while they lived there—the two most notable in 1910 and 1917, when the frame structure on the rear of the house was completed.

Dr. Holladay served the citizens of Orange County as their physician for nearly five decades. Prominently located at the crossroads in the Town of Orange, The Doctor Holladay House (as it was then called) was a familiar landmark in town. Educated at Hampton-Sydney College and the University of Virginia, Dr. Holladay was Dean of Physicians for Orange County throughout his medical career. In 1911, he was appointed a member of the State Board of Medical Examiners, where he served until his death. He was the Orange County Coroner, and the company surgeon for the Chesapeake and Ohio Railway. In addition to his medical career, Dr. Holladay served the town as Director of the National Bank of Orange, and as the ruling elder of Orange Presbyterian Church.

In the 1920s, the Holladays also constructed two new houses and a small schoolhouse on the property. The two houses still stand on the east and west sides of the Holladay House, but the schoolhouse is no longer extant.

Lewis and his wife had six children while they lived at the Holladay House. Their oldest, Louise, never married and lived in what is now the Oak Room for many years. She remained in the house all her life, and cared for Dr. Holladay after the death of her mother. Their youngest child, Aubry Price Holladay, married William Hamilton in the Holladay House parlor and moved into the house next door, on the west side. Henry Thompson was the oldest son. Lewis Holladay, Jr. and James Porter were twins, and Helen was their other younger sister.

After Dr. Holladay died in 1946, the house on the west side passed to his daughter Aubry. The house on the east side passed to his daughter Helen, and his son, James Porter. The main house passed to Louise and Lewis, Jr.

In 1984, Louise gave her interest in the property to her brother, Lewis Holladay, Jr. When he died, the property passed to his wife, Mildred. Mildred Holladay then passed the property to her son, Lewis “Pete” Holladay III.

The Holladay House Bed and Breakfast
(1989-present)
Lewis “Pete” Holladay III inherited the Holladay House in 1988 and established the Holladay House Bed and Breakfast. Pete and his wife Phebe renovated the property and created the charming Main Street inn that exists today. Well-known for their hospitality (and Pete’s award-winning apple muffins!), these innkeepers continued their family’s tradition of serving their community from this historic Main Street landmark. In the year 2000, after over 100 years of Holladay family ownership (12 of which were as a bed and breakfast), the property left the Holladay family; but their legacy continues. The Holladay House Bed and Breakfast has operated as an historic Virginia bed and breakfast since 1989, making it the oldest continuously operating bed and breakfast in Orange, Virginia.

The current innkeepers, Samuel and Sharon Elswick, purchased the Holladay House Bed and Breakfast in September 2006. Always conscious of their home’s antiquity, Sharon and Sam Elswick consider themselves to be the stewards of the Holladay House legacy, rather than its owners. The Holladay House has been central to the Main Street community since the early days of Orange, Virginia, and has survived as one of the oldest buildings on Main Street. It has witnessed the development of early Virginia, and provided its growing community with dry goods and supplies. It has had James Madison, the Father of the Constitution, pass by its front stoop. It has witnessed warfare in its streets, and observed the South’s greatest commanders going to worship. It survived the town’s most devastating calamity, the fire of 1908, when much of Orange completely burned to the ground. It has hosted weddings, birthed children, and reared families. It has helped heal the sick, and educate children. Truly, the Holladay House has left a deep impression in the colorful fabric of Orange history, and Sam and Sharon accept their stewardship with reverence and pride.

Visit the Holladay House Bed and Breakfast and steep yourself in the history of Orange, the history of Virginia, and the history of America.

Architectural History and Special Features
Coming Soon.