Live Music & Events

Events at Wayside Inn

The Wayside Inn in Middletown, Virginia is a popular destination for live music and entertainment. Located in the heart of town, the Inn provides an intimate atmosphere that allows guests to enjoy their favorite tunes while relaxing with friends and family.


The venue hosts a variety of musical acts ranging from local bands, to solo and duo artists and much more. With its cozy environment and great selection of music,
the Wayside Inn has become a go-to spot for live music fans throughout the area.

Valentine’s Day at the Wayside Inn

An Evening to Remember

This Valentine’s Day, let romance and history intertwine at the Wayside Inn.


We’re thrilled to announce that Michael Murphy, a renowned classical guitarist and Renaissance lute musician, will be performing live to create an unforgettable evening of music and charm.


✨ A specially curated Valentine’s menu is in the works—stay tuned for details!

Make your reservation today by calling (540) 869-1797. Celebrate love with a night of elegance, music, and delicious cuisine.


Don’t miss this one-of-a-kind Valentine’s experience!

Special Winter Room Rate Discount

Now through February 28th.


Enjoy up to $50 off room rates at Wayside Inn!

Start the new year with a cozy getaway to our historic inn. Whether you're planning a weekend retreat, a romantic escape, or a relaxing solo trip, this is the perfect opportunity to experience the charm of Wayside Inn at a special winter rate.


Don't miss out on this limited-time offer to make your stay even more memorable. Book now and take advantage of these incredible savings!


For reservations and details, contact us at (540) 869-1797 or click the book now button.

Friday, February 7th from 6pm-8pm

Join Us at the Wayside for Our Open Bluegrass Jam!


Are you a bluegrass enthusiast? Come on down to the Wayside Inn for our Open Bluegrass Jam and experience the magic of live music in a welcoming and friendly atmosphere. Local bluegrass artists will be showcasing their talents, and we invite you to bring your instruments and join in on the fun. Whether you're a seasoned player or just picking up an instrument for the first time, everyone is encouraged to participate.


All skill levels are welcome! This is a fantastic opportunity to learn from fellow musicians, share your own tunes, and enjoy the rich tradition of bluegrass music. Don’t play an instrument? No problem! Come and enjoy the music, clap along, and meet new friends.


Also check our Facebook page or call us 540-869-1797 for the latest events at The Wayside Inn!


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