Historical, Cultural, and Heritage Sites



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Presidential Mansions and Gardens

America’s greatest thinkers lived and died in Virginia’s Piedmont region. Steep yourself in the creation of American democracy and the prominent intellectual tradition left by our most influential founding fathers.

More presidents have hailed from Virginia than any other state, and 4 of them lived in the pastoral landscape that defines the region surrounding Orange, Virginia and the Holladay House Bed and Breakfast.

James Madison’s Montpelier

James Madison's Montpelier

(3 miles, 5 minute drive): From the Montpelier website: “Montpelier, nestled in the foothills of the Blue Ridge Mountains, was the lifelong home of James Madison. Madison was raised at Montpelier, lived here after his marriage to Dolly, returned here after his presidency, and died here in his study surrounded by the books and papers that marked so much of his life's work. It was at Montpelier where Madison researched past democracies and conceived of the system of government that became our republic . . . . In the splendor of the Virginia countryside, a national treasure is being recovered. Experience the rediscovery of the mind and the man who forged the framework of a nation, who created the Constitutional charter that defines our democracy, our thinking, our society.”

More than just a house, Montpelier offers a splendid array of activities for a variety of interests:

Thomas Jefferson’s Monticello

(29 miles,  45 minute drive): Thomas Jefferson was the quintessential Virginian. He loved Virginia, he loved America, and he loved democracy. One of the most remarkable thinkers of the last 250 years, Jefferson built an immortal legacy in the heart of Virginia wine country. Monticello is an amazing place, and is the only home in America listed on the UNESCO World Heritage List.

Monticello has established the Robert H. Smith Center and is offering tours of Montalto, a stunning mountain-top property next to Monticello. Montalto commands spectacular views of the Virginia piedmont, and one can literally see most of central Virginia from this gorgeous peak.

James Monroe’s Highland

(29 miles, 40-45 minute drive): From the Ash-Lawn Highland website: “Ash Lawn-Highland is an historic house museum, 535-acre working farm, and performing arts site in Albermarle County, Virginia. President James Monroe and his wife, Elizabeth Kortright Monroe of New York, owned Ash Lawn-Highland from 1793 to 1826 and made it their official residence from 1799 to 1823.”

Minutes from Monticello, Highland is an excellent compliment to the other Presidential homes in the region. In addition, the Ash Lawn Opera treats guests of the Holladay House to fine performing arts. Formerly located at the presidential home, the opera now performs at the Paramount Theater in Charlottesville.

Woodrow Wilson’s Manse

About one hour west of Orange, in the Shenandoah Valley town of Staunton, Virginia, one can find the Woodrow Wilson birthplace. The home is an authentically restored 1856 Victorian mansion, and includes a museum and Presidential Library.

Zachary Taylor’s Montebello

Although historians disagree about the precise birthplace of Zachary Taylor, most regard Montebello as the most likely site. Montebello is privately owned and closed to the public, but an historic marker designates the property. Zachary Taylor and James Madison were relatives. Taylor Park, a central landmark in Orange across the street from the Holladay House (and a frequent venue for intimate weddings and elopements), is named for the Taylor family.

Civil War Sites

The history of Orange County and Northern Virginia is inseparable from the history of the Civil War. The Confederate and Federal armies fought some of the most important battles of the Civil War in central Virginia. One can hardly drive anywhere within 30 miles of Orange without passing Civil War battlefields, hospitals, homes, encampments, and headquarters. Both Union and Confederate troops moved all over this area, as the Federals desperately tried to crack the Confederate defenses along the Rapidan River. In fact, a small cavalry battle was fought on Main Street in the Town of Orange, directly in front of the Holladay House Bed and Breakfast!

For a complete list and description of local Civil War sites, visit The Civil War Traveler website, and read the Central VirginiaPiedmont and Fredericksburg Area pages. A few highlights are described below:

Exchange Hotel and Civil War Medical Museum

The Exchange Hotel and Civil War Medical Museum is a delightful and informative museum, with Civil War artifacts, medical artifacts, and gift shop. This historic hotel was a triage center and hospital for Civil War soldiers, and the museum focuses on the medical history and practices of Civil War surgeons. Not for the faint of heart, evening ghost tours are available Friday nights - but book early as they sell out quickly! The Exchange Hotel also boasts one of the best collections of authentic Civil War uniforms you are likely to see.

Ellwood Manor at the Wilderness Battlefield

Ellwood Manor: A restored plantation home that was an integral part of the bloody catastrophe called the Battle of the Wilderness. This serene country property was occupied by both Confederate and Union forces during the Civil War, and is the burial site of Stonewall Jackson's left arm.

Civil War Battlefields

The Wilderness Battlefield

Wilderness Battlefield: According to the National Park Service, “The Battle of the Wilderness was fought on May 5-6, 1864. It was the beginning of the Overland Campaign, the bloodiest campaign in American history and the turning point in the war in the Eastern Theatre.”

Chancellorsville, Fredericksburg, and Spotsylvania Battlefields: The bloodiest landscape in North America. Chancellorsville is the site where Stonewall Jackson’s own men shot and wounded him. According to the National Park Service, “No place more vividly reflects the Civil War’s tragic cost, in all its forms. These places reveal the trials of a community and nation at war.”

Other notable battles:

Saint Thomas Episcopal Church

St. Thomas Episcopal Church

St. Thomas Episcopal Church: One block away from the Holladay House Bed and Breakfast, the St. Thomas Episcopal church is rich in Civil War history. Used as a confederate hospital after the several battles fought in this region, this church was also where Robert E. Lee, A.P. Hill, Jefferson Davis, and other confederate leaders worshipped while Lee’s Army was encamped here in 1864. The famous American painter Mort Kunstler immortalized this church in his painting Soldier of Faith.

Colonial Revolutionary War Sites

Virginia historic sites abound in our region, and are too numerous to list here. However, our region is noted for being the gateway to colonizing the eighteenth century western frontier.

Fort Germanna Monument

Fort Germanna is the earliest German settlement in America, and many Americans of German descent can trace their ancestry back to this fort. Governor Alexander Spotswood pushed the colonial boundaries into the frontier in 1714, settling Fort Germanna and Fort Christanna in the Virginia hinterlands. The Brawdus Martin Germanna Visitor Center is architecturally interesting in its own right, and houses a research center for those interested in German genealogy and the history of Fort Germanna.

Michie Tavern: Historic Michie Tavern, established in 1784 by Scotsman William Michie, served as the social center of its community and accommodated travelers with food, drink and lodging. In addition to offering fascinating tours, Michie Tavern also serves hearty colonial fare in their dining room from 11:30am until 3pm. Michie Tavern is a fantastic compliment to a presidential home tour.

Historic Gardens

In addition to the fabulous gardens located on the properties of Presidential homes such as Monticello and Montpelier, the Virginia Piedmont is home to a number of other historic gardens. Virginia Garden Week is a fantastic opportunity to enjoy the Virginia weather and explore over 250 historic sites and gardens.



James Madison Museum: Orange, VA, The Museum’s mission is to preserve and present the remarkable history of Orange County, along with the contributions of James Madison, Dolley Madison and Orange-born President Zachary Taylor. Boasting a large collection of agricultural implements and 1732 cube house, the Black History Room conveying the intertwined history of Black Americans from the American Revolution onward through Post-Emancipation, the Madison Room displaying numerous possessions of the Madisons, Taylor, Washington, Jefferson and Monroe, and the Temporary Exhibit Room which often showcases historic fashions.

Civil War Museum at the Exchange Hotel: Gordonsville, VA, The Exchange Hotel stands silent watch over a rich past that intertwines Civil War medicine, military actions of the Army of Northern Virginia, and the mighty railroads of Virginia. Visit this unique building and experience Gordonsville's personal history through medical, military, town, and hotel exhibits. After-dark Friday ghost tours available by booking early.

Vietnam War Foundation and Museum: The Vietnam War Foundation (VWF) is dedicated to presenting the Vietnam Era story through narration and static displays of actual equipment used by the men and women who served in VN during the 10 years of conflict. This mission is accomplished through the acquisition, restoration and maintenance of historic vehicles (trucks, aircraft, jeeps, APCs, etc.), VN era memorabilia, VC artifacts, weapons, and civilian and peace symbols of the Vietnam Era. The VWF provides the opportunity to hear its veterans share their stories and see its military legacy.

Museum of Culpeper History: Culpeper, VA, A museum dedicated to the history of Culpeper County: from the Paleolithic age all the way through to the current age. On the Museum campus, visitors can enjoy both the Burgandine House, a fully restored 18th century log cabin and a working American Indian Village. The grounds are complete with ample green space for picnicking and outdoor programs as well as a spacious parking area.

Orange County Historical Society and Historical Research Center: A research, archival, and educational organization dedicated to the discovery, preservation, and dissemination of the history of Orange County, Virginia, of its people, and the surrounding area. The Society's reference library contains over 2,000 volumes, and there are over 1,300 files with information on families, historic buildings, events and sites, plus a map and photograph collection.

Journey Through Hallowed Ground

The Journey Through Hallowed Ground is a National Register of Historic Places Travel Itinerary designed to explore 65 historic places along the Route 15 corridor. According to the National Park Service, "these sites evoke in vivid detail the soldiers, statesmen, farmers, and slaves who fought, toiled, and governed in the Virginia Piedmont."

Other Historic Architecture

University of Virginia Academical Village

Barboursville Ruins