Travelers to the Inn started arriving in 1797, pausing for bed and board as they journeyed across the beautiful Shenandoah Valley. Wayside Inn, was then known as Wilkenson's Tavern. Rugged highways were hacked out of the wilderness 20 years later, and the Valley Pike, now Route 11, came through Middletown. The tavern became a stagecoach stop-- a relay station where fresh horses were readied and bounce-weary passengers could rest and refresh themselves.
In coaching days, a servant boy would be sent to the nearby hill to sight an expected stagecoach. When a cloud of dust appeared over the horizon, he waited anxiously, straining to sight the outline of the stagecoach, and then hurried back to the Inn to report its approach. By the time the passengers arrived, delicious hot food would be waiting and they would dine and drink in comfort while the team of horses was being changed.
During the Civil War, soldiers from both the North and South frequented the Inn in search of refuge and friendship. Serving both sides in this devastating conflict, the Inn offered comfort to all and was spared the ravages of the war, even though Stonewall Jackson's famous Valley Campaign swept past only a few miles away.
In the 1960's a Washington financier and antique collector, Leo M. Bernstein, owner the Inn for nearly 50 years. Recently the inn was purchased by HGH Finnigan Resources. Wayside Inn is being leased by RAO Hospitality LLC.
The new innkeepers, Rich & Angie Orndorff hope to bring back the wonderful ambiance of the days of the Bernstein era.
"The Top of Virginia Regional Chamber is an incredibly valuable resource for the Shenandoah Valley..." – Adrienne G. Bloss, PhD, Provost, Shenandoah University.