Nestled in the heart of Virginia’s beautiful Shenandoah Valley, we’ve been welcoming travelers to Middletown since 1797. We’re America’s oldest continuously operating inn and the nation’s pioneering motor inn. That’s not marketing language. That’s 225 years of unbroken hospitality, adaptation, and survival.

Chain hotels offer predictability. Clean rooms. Free breakfast. Reliable sameness in every city across America. You know exactly what you’re getting, and you’ll forget you were there by next week.

The Historic Wayside Inn 1797 offers something different: an experience you can’t replicate. When you stay with us, you’re sleeping in a building that predates The Declaration of Independence. You’re walking halls where Civil War generals sought refuge, where presidents rested, where Hollywood stars checked in specifically because this place is unrepeatable. Our 22 individually decorated guest rooms feature authentic 19th-century antiques and period details. No two are alike. Each has its own character, its own story, and yes, its own modern private bathroom because we believe history should be comfortable.

This is a place with a soul. You’ll feel it the moment you walk through the door. Our guests don’t just come once. They come back. They bring their children. Their grandchildren. They celebrate anniversaries here, host weddings here, return year after year because some places become part of your story.

The difference between staying here and staying anywhere else? When you check out of a chain hotel, you leave. When you check out of the Wayside, you take a piece of it with you. And you’ll want to come back.

Experience the Difference

Our historic tours run year-round, revealing stories spanning nearly three centuries. Our event spaces host celebrations that deserve a backdrop with meaning. Our restaurant serves meals in rooms that have welcomed guests since before your great-great-grandparents were born.

This is what authentic feels like. This is what matters.

Ready to experience something real? Call us at (540) 869-1797 or book online.

The Wayside Inn: Where history isn’t preserved behind glass. It’s lived.