The Wayside Inn, is nestled in the beautiful Shenandoah Valley of Virginia in Middletown, Virginia.  Since 1797, it has offered accommodations, dining and entertainment to visitors, and has been a host of weddings, community and special events. Wayside Inn, is a truly unique experience, boasting as the oldest and longest continuously run Inn, in the United States. The oldest part "Old Kitchen" was built as a waystation & stagecoach stop built in 1742 along with the well that watered the town.

Our Rooms

With twenty-one newly refurbished bedrooms and bathrooms, we are sure to have the perfect place to rest your head.  Whether it's for a family vacation, a weekend getaway, a wedding or a family reunion.

Spa Towels with Flower


  • Free Wi-Fi

  • Free Parking

  • Kid Friendly

  • On-Site Dining

  • Smoke-Free

  • No Pets

  • Fresh Towels

  • In-Room TV

  • Air Conditioning

Wedding Cake

Weddings & Events

The Wayside Inn is the perfect place for your outdoor or rustic-style wedding.  The Wayside Inn offers a beautiful historic wedding venue (inside or outside), catering and overnight accommodations for all of your guests.

Main Dining Room.jpg

Dining Rooms

We have a variety of dining room options available, depending on the dining experience you're looking for.  Personal, small gatherings, large reunions, business meetings or weddings.


Larrick's Tavern

Larrick's Tavern offers a wide variety of good ole' comfort food, crafted and prepared by Executive Chef Travis Ross, as well as a full bar.

Currently open Wednesday - Sunday, beginning at 4pm.

Image by Jefferson Santos

Live Music

Join us for Live music and Entertainment.