The Haunted Wayside Inn, Middletown, Virginia: Lord Fairfax's Moan and the Soldiers of the Valley Pike

The Wayside Inn sits on Main Street in Middletown, a small Shenandoah Valley town on what was once the Valley Pike, the main road up and down the valley. Travelers have been stopping here since 1797, when it was a stagecoach stop called Wilkenson’s Tavern, and its oldest part, the Old Kitchen, is said to date to 1742. It has 22 rooms and suites furnished with antiques, Larrick’s Tavern with the town’s old well inside it, and a restaurant, Clem’s Kitchen.

For decades the inn has been called one of the most haunted in Virginia. Former owner Leo Bernstein liked to tell visitors about the moan heard from a small loft above one of the bars, which legend pins on Lord Fairfax. Staff and guests describe objects moving, a dishwasher whose apron kept being untied, Civil War soldiers in the halls and two guest rooms with stories of their own. This guide sets out the stories, the history and how to plan a stay. If you are looking for the Wayside Inn in Ellicott City, Maryland, that is a different inn, with its own guide.

The ghosts of The Wayside Inn, Middletown

The moan in the loft

The Wayside Inn’s signature story is a sound. In the oldest part of the building, above one of the bars, is a low loft, about three feet high, reached by a set of steps. Leo Bernstein, who owned the inn from the 1960s, described it to author Sheila Turnage for her book Haunted Inns of the Southeast: there were steps going up, he said, and the straw was still there.

From that loft, the story goes, comes a moan every night. Turnage reported that people would gather around 11:30 at night to listen for it. Legend blames Lord Fairfax, the colonial landowner who lived nearby and died in Winchester. There is no record linking him to the building, and Bernstein was a famous storyteller, so take the attribution with a smile.

Civil War soldiers

Armies from both sides marched up and down the Valley Pike during the Civil War, and soldiers from the North and the South stayed at the inn. Unlike much of the valley, it came through the war undamaged. Full apparitions of Civil War soldiers have been reported in the halls and the lobby, and the guides who include the Wayside describe them as friendly. Paranormal investigators say they have recorded what sound like horses whinnying, which fits a building that began as a stagecoach stop.

The prankster in the kitchen

Not all the stories are solemn. Staff have told of objects moving by themselves, and one dishwasher kept finding his apron untied by hands nobody could see. Footsteps and voices in empty parts of the inn round out the accounts.

The two haunted rooms

Visit Winchester, the regional tourism office, notes that guests can choose to stay in one of the two guest rooms that are rumored to be haunted. The inn does not publish which two they are, so ask the staff when you book or at check-in. An earlier version of our own guide said the inn served as a Civil War hospital; we have found no source for that, so we have left it out.

The most haunted rooms and places to look

• The two haunted rooms: Not named online. Call the inn and ask which rooms have the stories before you book.
• Grand Entrance rooms: Eleven rooms in the main building, including the Jubal Early and Reeves State Rooms and the Cedar Creek room, named for the 1864 battle fought just outside town.
• South Wing: Eight rooms named for Virginia people and places, among them Lee, Shenandoah, Massanutten and Monroe.
• North Wing suites: The Rhodes Suite, the Bernstein Suite, named for the owner who restored the inn, and the Washington State Room.

History of The Wayside Inn, Middletown

Middletown grew up along the Valley Pike, the road that carried settlers, freight and armies through the Shenandoah Valley. The inn’s oldest section, the Old Kitchen, is said to have been built as a waystation and stagecoach stop in 1742. The first travelers recorded at the inn came in 1797, when it was known as Wilkenson’s Tavern, and the well inside today’s tavern once supplied water to the town.

During the Civil War both armies moved through Middletown again and again, and the Battle of Cedar Creek was fought just south of town in October 1864. Soldiers of the North and the South stayed at the inn, and it came through the war undamaged.

In the 1960s Washington banker and developer Leo Bernstein bought the inn, restored it and filled it with antiques and art. He claimed it was the oldest continuously operating inn in the nation, a claim no one has proven, and he was happy to share its ghost stories with visitors and writers.

George and Becky Reeves bought the Wayside Inn in 2013 for $806,250 and owned it for seven years before selling it for $650,000 to HGH Finnigan Resources around the start of 2021, according to the Northern Virginia Daily. Today it has 22 rooms and suites in three wings, seven dining rooms, reading rooms, Larrick’s Tavern and Clem’s Kitchen, which serves breakfast, lunch, dinner and Sunday brunch. The inn now leans into its reputation, with guest reviews on its website describing ghost tours.

Tips for a haunted stay

• Call before you book and ask which two rooms have the stories; the inn does not list them online.
• Ask whether a ghost tour is running during your stay: the inn’s own website features guest reviews from people who came for one, along with a press feature naming it Virginia’s most haunted hotel.
• Have a late drink in Larrick’s Tavern and look down the old town well. The loft with the moan is above one of the bars.
• If you are bringing a dog, book one of the three pet-friendly rooms early.
• Check the dining days: Clem’s Kitchen is open Thursday to Sunday.
• Walk the Cedar Creek and Belle Grove National Historical Park just south of town, the battlefield behind many of the soldier stories.
• Read the cancellation terms when you book direct: there are fees from 14 days before arrival.

More haunted hotels nearby

• By the Side of the Road, Harrisonburg: a Civil War-era house turned inn, further up the valley
• The Lafayette Inn, Stanardsville: a soldier’s ghost on the far side of the Blue Ridge
• The Wayside Inn, Ellicott City, Maryland: the other haunted Wayside Inn, often confused with this one
• Haunted hotels in Virginia

Sources

Facts on this page are checked against the hotel’s own website, historic records and news coverage. Ghost stories are reported as guests, staff and local historians tell them. Read how we rate haunted hotels.

• The Wayside Inn: official site
• Visit Winchester: Wayside Inn
• Southern Spirit Guide: A spectral tour of the Shenandoah Valley
• Northern Virginia Daily: Middletown's Wayside Inn sold
• OnlyInYourState: Haunted hotels in Virginia

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