Wayside Inn – America’s Oldest Continuous Inn – Middletown, VA

The Wayside Inn in Middletown, VA, has the distinction of being known as the oldestWayside Inn, Middletown, VA continuous Inn in the United States (there may be some question about that claim).  When you’re there, you can see why. It still has the flair of an early American Inn.  It opened in 1797 for travelers passing through the Shenandoah Valley, and it is open today for modern day travelers.

A number of years ago, I had five office assistants.  During the Christmas holidays, I gave each one a gift of a night at the Inn along with a wonderful dinner there.  They all raved about the accommodations, and they loved the food.  I also love the food at Wayside.  It’s always very well prepared, unique in its presentation and delicious to the last bite.

The Inn survived the Civil War as both northern and southern troops dropped in for a respite from the stress of battle.  Stonewall Jackson’s valley campaign took place just aWayside Inn, Middletown, VA few miles down Valley Pike from where the Inn is located.

As the Inn entered the age of automobiles, it became known as “America’s First Motor Inn.”  Valley Pike was transformed from a pot-hole pitted dirt road to an asphalt coated highway, and more and more visitors arrived at the Inn.

The Inn is furnished with 100s of antiques throughout, and because of that, it maintains its 18th century charm.  The Inn boasts of several dining areas, and it hosts weddings, receptions and local events.  I often took my fitness studio and church staffs to lunch there.  We all loved it so much that it became a regular stop on our calendar.

If you are passing through the Winchester / Frederick County area, plan to make a stop at the Wayside Inn.  You can feel the history as soon as you walk in the door.  It’s a real piece of Americana.


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