Weddings & Events

The Wayside Inn in Middletown, Virginia, is a stunning and historic wedding destination, offering a variety of unique spaces for both ceremonies and receptions.


With 22 cozy guest rooms available for overnight accommodations, the Inn provides a perfect gathering place for couples, families, and friends to celebrate together. Its rustic charm and historic ambiance create a timeless backdrop for intimate and traditional weddings.


Our on-site culinary team is celebrated for crafting delicious, locally-inspired cuisine that adds a memorable touch to your special day. From custom menus to flawless service, we’re here to make your celebration seamless and stress-free.

Located in a peaceful, scenic corner of the Shenandoah Valley, the Inn offers both beauty and tranquility—ideal for a relaxed and meaningful experience.


In addition to the Inn’s main offerings, we are excited to introduce O’Proa’s Irish Cantina, now open within our historic property. This warm and festive space is perfect for rehearsal dinners, welcome receptions, or casual gatherings during your wedding weekend.


The O’Proa’s Event Team is now proudly assisting with Wayside-hosted events.


For inquiries related to events or to begin planning your celebration:


We look forward to helping you create an unforgettable celebration!