The Wayside Inn

Posted: 05.28.2025 | Updated: 05.28.2025

The Wayside Inn is located in the heart of Middletown, Virginia, nestled in the scenic Shenandoah Valley. This historic inn has welcomed travelers since 1797, making it the oldest continuously operating inn in the United States. Guests come for its charm, hospitality, and rich history. However, the inn’s reputation draws others for its ghostly encounters.

Check out Alexandria Ghosts for chilling tours and stories from Virginia’s most historic towns if you want more haunted adventures.

Is the Wayside Inn Haunted? 

Many guests and staff believe it is. The most talked-about spirits are the woman in blue, the restless presence in Room 14, playful ghostly children, and Civil War soldiers. Visitors often report footsteps, cold spots, flickering lights, and shadowy figures in empty rooms. 

Some guests have experienced emotional changes or felt watched, especially in Room 14. While no scientific proof exists, the sheer number of stories and encounters is hard to ignore. The inn’s long history, dramatic events, and welcoming atmosphere have created a place where the past feels very close. 

History of Wayside Inn

The Wayside Inn began as a waystation and stagecoach stop in the 1740s. It’s original “Old Kitchen” well served early travelers and the hamlet of Middletown.

By 1797, the inn was officially established and became known as Wilkinson’s Tavern. It offered food, lodging, and rest to those journeying through the Shenandoah Valley. As the Valley Pike (now Route 11) was developed, the inn became a busy relay station for stagecoaches, where weary passengers could refresh themselves while horses were changed.

Hospitality at the Wayside Inn continued into the 19th century. The inn’s historic taste is still evident in its 22 individually appointed guest rooms and refurbished public spaces.

During the Civil War, the Wayside Inn played a unique role in providing shelter, food, and fellowship for Union and Confederate forces. The inn was even used as a makeshift hospital for wounded soldiers, but it was untouched, even if the region was at war.

Over the years, the inn experienced various ownership and reconstruction phases. The most important, however, was Leo Bernstein’s acquisition and rebuilding of the property in the mid-20th century.

Today, the Wayside Inn remains the oldest inn in the United States and is still open for business. It welcomes visitors with a combination of historic refinement and legendary hospitality.

The Hauntings at Wayside Inn

With such a history-rich past, the Wayside Inn is a favorite haunt among ghost hunters. Guests and staff members have felt cold spots, flickering lights, and ghostly footfalls along empty corridors. Its Civil War history, tales of tragedy, and tales of previous owners’ legends have all lent the inn its haunted reputation.

A few of the spirits are friendly ones, while others are simply curious. The encounters have become a part of the inn’s special attraction.

The Woman in Blue

The Woman in Blue is one of the Wayside Inn’s most frequently seen spirits. She’s described as wearing a high-collared blue dress, appearing like she stepped out of another era. 

Guests and staff have seen her floating through the lobby or near the fireplace, often leaving behind a sudden chill or cold spot.

Some visitors report glimpsing her reflection in mirrors or catching her out of the corner of their eye. She’s considered gentle and calm, with many believing she’s a former guest or staff member from the 1800s.

Others think that she may be connected with the inn’s history of the Civil War. She is sometimes paired with short whispers or the sensation of someone watching her, especially at night. The Woman in Blue is not considered to be threatening.

Instead, she adds a presence of mystery and history to the inn’s atmosphere.

Her story and frequent sightings have made her one of the most enduring and talked-about spirits at the Wayside Inn.

The Spirits of Room 14

Room 14 is widely considered the most haunted room at the Wayside Inn. Guests have reported a variety of strange experiences in this room, including hearing heavy footsteps moving from the sitting room to the bathroom when no one is present.

Some guests have felt cold touches at night or noticed the room suddenly freezing cold. Others have seen lights flicker, felt watched, or experienced sudden waves of sadness or confusion.

Ghost investigators have focused on Room 14, using EMF detectors and spirit boxes to capture unexplained voices and document sudden temperature drops. 

One visitor placed cat ball lights on the carpet and watched them flash as if touched by unseen hands. Some guests have even blacked out or felt compelled to avoid the bathroom altogether. 

Despite these eerie events, most visitors say the spirits in Room 14 are not harmful. Instead, they contribute to the room’s mysterious and unforgettable reputation, making it a favorite for ghost hunters and thrill-seekers.

Ghostly Children and Civil War Soldiers

The Wayside Inn’s history as a Civil War hospital and stagecoach stop has left a lasting mark. Guests and staff have reported hearing children running and laughing in empty hallways. Some have also seen the ghost of a young boy darting around corners or hiding behind furniture as if playing hide-and-seek.

The inn is also home to the spirit of a Confederate soldier, seen wandering the halls in uniform, especially in the early morning hours. Witnesses have heard the heavy clomp of boots in the corridors and even seen the soldier disappear around corners. 

Servers have reported dishes flying off shelves in the old slave kitchen and feeling something brush their arms while working. These spirits are a mix of playful children and watchful soldiers. Both types of ghosts add to the inn’s haunted legacy.

The echoes of the past are felt throughout the building, from the lobby to the oldest guest rooms. This makes every stay a brush with history and possible ghostly interactions.

Unexplained Activity and Other Spirits

Beyond the main ghost stories, the Wayside Inn is a hotspot for unexplained activity. Guests have found coins rearranged into the letter “L” on their nightstands, a phenomenon reported by several visitors. 

Cold spots are often felt near the lobby fireplace. Some have caught shadowy figures on camera in the old kitchen area. Lights flicker, doors open independently, and strange noises echo through empty rooms.

Staff members report feeling watched or followed, especially while closing up at night. The ballroom is another haunted area, where guests have heard old-fashioned waltz music or seen shadowy dancers vanish when approached. 

Ghost investigators have captured orbs, unexplained voices, and sudden temperature drops throughout the inn. These mysterious happenings make the Wayside Inn a favorite destination for ghost hunters and curious travelers. Its reputation as one of Virginia’s most haunted and intriguing places continues to grow.

Haunted Middletown

The Wayside Inn is not just an old Middletown hotel—it’s a living history museum of Virginia. Its walls have witnessed centuries of visitors, soldiers, bashes, and tragedy. To many who come, those voices of the past haunt it in ghostly apparitions. Visit it for its rich history, comfortable rooms, or reputation as a haunted site, and a visit will be one you’ll not soon forget.

 If you’re eager to explore even more haunted stories and mysterious sites, don’t miss the chance to join an Alexandria Ghost tour. You’ll discover that in Virginia, the past is never far away—and sometimes, it’s closer than you think. Follow us on Facebook, Instagram, and TikTok, and keep reading our blog for more real Middletown hauntings.

Sources:

1. https://www.onlyinyourstate.com/stays/virginia/wayside-inn-most-haunted-va
2. https://www.youtube.com/watch?v=Jq4O7Aw4PCM
3. https://visitwinchesterva.com/locations/wayside-inn/
4. https://reverendvsjohnson.medium.com/the-haunted-wayside-inn-cd0dd81f7281