Holladay House: 1849-1883

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


Holladay House Historic District    Soldier of Faith by Mort Kunstler        Portrait of Dr. Lewis Holladay, ca. 1940    An Historic Bed and Breakfast in Virginia
1830-1849  1849-1883  1883-1899  1899-1989    1989-Present


The Chapman Family and the American Civil War

John Madison Chapman (1810-1879) married Susan Digges Cole in 1841 and acquired the Holladay House property in 1849. He and his family resided here for 35 years, during some of the most tumultuous times in American history. From inside this home’s walls, the Chapmans witnessed the fracture of a nation, watched the horrors of industrialized war as it was waged literally on their front stoop, felt the bitterness of defeat, and experienced the reconstruction of an economy and a society. If only this bed and breakfast in Virginia could recount the myriad conversations that took place in the Chapman’s parlor!

Civil War Map of Orange, Virginia

 Civil War Map of Orange, zoomed on the Chapman House

Civil War map of the Town of Orange, Virginia, showing the area where Federal and Confederate Cavalry clashed, leaving 20-50 Americans dead. The Chapman House (now the Holladay House Bed and Breakfast), the Orange County Court House, and St. Thomas Episcopal Church (where Robert E. Lee frequently worshipped) are all indicated.

For more information on the Civil War in Virginia, visit our Civil War Sesquicentennial page.


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 corresponded with James Madison on a number of topics. John Madison Chapman’s mother, Rebecca Conway Madison Chapman (1785–1861), was the daughter of James Madison’s younger brother, William Madison (making John Madison Chapman the grand-nephew of President James Madison).

John Madison Chapman was a well-connected lawyer in Orange, VA, and presumably operated his practice from his newly acquired house on Main Street. In 1855, he was a trustee for the town’s incorporation, but the Town of Orange was not incorporated until 1872.

The American Civil War was a troubling time for the Chapmans. As slave holders (at least two enslaved Africans resided with the Chapmans in 1860, probably as personal attendants for the family), the Chapmans supported the Confederate cause and had a vested interest in the war’s outcome. John Madison Chapman’s mother died in 1861, and in August 1862 bitter fighting came to the Chapman's doorstep as approximately 200 men from the Seventh Virginia Cavalry successfully repulsed over 1000 men of the First Vermont Cavalry. Naturally, the historical accounts vary, but at the end of the fight 20 - 50 men and a dozen or more horses from both sides laid dead on Main Street and throughout the town. You may read the official accounts of the battle at our Civil War Sesquicentennial page. 

 Unconquered Spirit, painting by Mort Kunstler

Unconquered Spirit, by famous artist of historical subjects, Mort Kunstler. The painting depicts General Lee’s arrival at Orange Courthouse after his defeat at Gettysburg. The Orange County Courthouse in the background was constructed in 1859.


Orange County Courthouse, built in 1859


Modern photograph of the historic Orange County Courthouse, only two blocks from the Chapman House. The Chapman House is now the Holladay House Bed and Breakfast, and offers lodging accommodations in Orange, VA. The courthouse remains an iconic historic land mark in the Town of Orange, Virginia.


In 1863, Robert E. Lee marched his army from Gettysburg to take up defensive positions in Orange County. During the wet and cold winter (as reported by a diarist of the time), Chapman’s daughter, Emma, married Robert Boykin at St. Thomas Episcopal Church, the same church where Robert E. Lee worshipped, and which still stands today. Boykin was an officer in Lee’s army, and a number of well-known Confederates attended the reception. By all accounts, the wedding reception was a rousing good time! A hospital steward in the Confederate army who attended the event wrote the following:

For the party I must say it did honour to the family. The pride and chivalry of the A.N.V. [Army of Northern Virginia] were well represented. A finer looking set of gentlemen, prettier girls, and a livlier party perhaps will not be assembled soon again. Among the distinguished characters were Maj. Gen'ls [James Ewell Brown] Stuart & [Robert Emmett] Rhodes and Brig: Gen'ls [Robert Hall] Chilton & [Edward Aylesworth] Perry. Then staff officers of all grades--Surgeons and Q.M.'s The bride was lovely indeed . . . . The supper was a magnificent one--Dr. Crane and myself were on an equality and left about mid-night. The dance was kept up 'till about 4 o'clock in the morning.

It appears that, even in the aftermath of horrifying death and bitter defeat at Gettysburg, the dashing J.E.B Stuart and other Confederate officers could still party hard at the Holladay House until the early morning hours! For complete details and the diarist’s entire account, see our Civil War history page.

If you would like to hold your own wedding or rousing reception at this historic wedding venue in Virginia, see our Weddings page!


Soldier of Faith depicts General Robert E. Lee riding by St. Thomas Episcopal Church in the winter of 1863/64, painted by renowned Civil War artist,Mort Kunstler. This church was also the site of the marriage of Emma Chapman and Robert Boykin, and is only one block from our Bed and Breakfast in Virginia.


 St. Thomas Episcopal Church has not changed much since it was used as a Civil War hospital and since Robert E. Lee attended services there. General Lee’s pew is on display inside, and the original wooden floors, still stained by the blood of Confederate soldiers, are still extant (although underneath subsequent floors). At least one of the stunning stained glass windows is an authentic Tiffany window.

After the war, John Madison Chapman had a distinguished career as a lawyer and politician. From 1869 to 1870, Chapman was a presiding justice for the Orange County court, and from 1874 until his death in 1879, Chapman served as Mayor of the Town of Orange. In October 1878 he was a part of the committee to greet President Rutherford B. Hayes when Hayes visited Orange, VA.

Prominent and wealthy 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.


Follow the links below for more historical information!


1830 - 1849: Construction and Early Residents

1849 - 1883: The Chapman Family and the American Civil War

1883 - 1899: MacDonald Family and the Methodist Parsonage

1899 - 1989: The Holladay Family

1989 - Present: Holladay House Bed and Breakfast


For information about local historical sites and heritage tourism, see our Travel Guide for Charlottesville, Orange, and Central Virginia.

To begin an adventure into history, visit our Virginia Travel Packages page, which includes special packages and itineraries for Heritage Tourism, Archaeology Travel, Civil War Sesquicentennial Events, and Civil War Tours.