Operating since 1797 in the Shenandoah Valley, the Wayside Inn served as lodging and hospital to both Union and Confederate forces; guests report a Woman in Blue, cold spots, and disembodied footsteps.
7783 Main Street, Middletown, VA 22645
Research updated June 2026
Age
All Ages
Cost
$$
Room rates for overnight stays; ghost tours and paranormal hunts separately ticketed. Check website for current pricing.
Access
Limited Access
18th-century inn with multiple levels; original construction predates modern accessibility standards.
Equipment
Photos OK
Est. 1797 · Cited as oldest continuously operating inn in the United States, in service since 1797 · Located on the Valley Pike contested during three Civil War Shenandoah Valley campaigns, 1862-1864 · Served as lodging and hospital for Union and Confederate soldiers
The Valley Pike through the Shenandoah Valley carried travelers, armies, and commerce for centuries, and the property at what is now 7783 Main Street in Middletown has offered accommodations along that route since at least the 1740s. The official founding date given by the inn is 1797, though some accounts trace activity on the site to as early as 1742. Virginia historical organizations have recognized the Wayside as the oldest continuously operating inn in the United States.
The inn's Civil War chapter was neither brief nor incidental. The Shenandoah Valley was the subject of three distinct military campaigns between 1862 and 1864. Thomas 'Stonewall' Jackson's Valley Campaign of 1862 moved Confederate forces up and down the Valley turnpike at speed; the Second Shenandoah Campaign in 1864 brought Philip Sheridan's Union forces into the Valley with explicit orders to destroy its agricultural capacity; and fighting at Cedar Creek and Fisher's Hill occurred within miles of Middletown. The inn served soldiers of both armies as they moved through, and parts of the building functioned as a hospital during periods of combat.
The building has been operated as an inn continuously since the 18th century, passing through many proprietors but maintaining its original function. It includes a period-furnished dining room and multiple guest rooms. The surrounding village of Middletown retains significant Civil War-era architecture, and several ghost tour operators from the Shenandoah Valley area include the Wayside on their routing.
Sources
An inn in continuous operation since 1797, serving soldiers and civilians through three Civil War campaigns, produces a long and layered paranormal tradition. The Wayside Inn's accounts run from ambient phenomena — cold spots in specific rooms, footsteps in empty hallways — to the more distinct figure of the Woman in Blue.
The Woman in Blue is the most consistently reported entity. Accounts describe a female figure in period dress, appearing in hallways and occasionally in guest rooms, who retreats or disappears when approached. She lacks a well-documented historical identity; the name is a descriptive handle that emerged from repeated, independent sightings rather than a named historical person.
Paranormal investigators working the property have documented orbs in photographs and anomalous readings in equipment-based investigations. The Virginia Haunted Houses database lists the Wayside among its documented real haunts, citing cold spots and captured paranormal evidence. Ghost tour operators out of Alexandria and the northern Shenandoah area include the inn on their programming.
The inn's 18th-century construction means the building has accumulated history well beyond the Civil War — generations of travelers, illness, and ordinary life unfolded here before the first shot was fired. The reported activity is not clustered exclusively around the war years, which is consistent with a building of this age.
Notable Entities
Book a room at what is widely cited as the oldest continuously operating inn in the United States — in continuous service since at least 1797. The inn sits on a stretch of the Valley Pike (now Main Street) contested repeatedly during the Civil War's Shenandoah Valley campaigns.
The inn offers ghost tours and occasional paranormal hunts featuring the building's history as a Civil War lodging and hospital. The Woman in Blue and other reported entities are covered in guided sessions.
Every HauntBound history is researched from documented sources. We clearly separate verified historical fact from paranormal folklore.
Long Beach, CA
The RMS Queen Mary was constructed at John Brown & Company's Clydebank shipyard beginning in 1930, launched September 26, 1934, and sailed her maiden voyage on May 27, 1936. Requisitioned as a troopship in 1939, she carried 810,000 soldiers under the nickname 'The Grey Ghost.' The ship has been permanently moored in Long Beach, California since December 1967.
Eureka Springs, AR
The 1886 Crescent Hotel was built as a luxury Victorian resort atop the Ozark mountains of Eureka Springs, Arkansas, then briefly operated as a women's college before its most notorious chapter: Norman Baker's fraudulent cancer clinic from 1937 to 1940. Baker charged dying patients for treatments that offered no medical benefit, and the hotel retains his intact basement morgue.
Eureka Springs, AR
The 1905 Basin Park Hotel is a seven-story limestone hotel in downtown Eureka Springs, Arkansas, built on the site of the Perry House, an 1881 hotel that burned in 1890. The Basin Park's distinctive limestone-cut design, with every floor opening at ground level on its hillside, was featured by Ripley's Believe It or Not.