Local Attractions

The Wayside Inn is located in Middletown, Virginia, a small town located in the Shenandoah Valley and is home to a variety of attractions including Civil War sites. Middletown started as one of a series of settlements that sprang up along the Valley Pike within the boundaries of the 17th Century Fairfax Grant. Middletown earned a place in our national history through its association with prominent historical figures in both the colonial and Civil War eras.

The town has several outdoor activities, such as hiking, biking, and fishing. The nearby Shenandoah National Park offers a variety of trails, scenic views, and is a great place to explore the area's rich history; Belle Grove Plantation, Cedar Creek Battle Field and Museum. Local town events include a 4th of July Parade and Christmas Parade,

Close by, you have the historic town of Winchester, Strasburg, Front Royal, and others. All with quaint restaurants, antique store and other local attractions to explore. Talk with our staff, we will help you plan the perfect exploration.

160th Anniversary Reenactment of the Battle of Cedar Creek

October, 19 & 20th, 2024

History comes to life during this special weekend event on the original grounds, the first preserved piece of the Cedar Creek Battlefield (1988), 160 years to the day after the engagement!

During this two day event, the Cedar Creek Battlefield Foundation's largest fundraiser of the year, reenactors recreate the last major battle in the Shenandoah Valley. See cavalry, artillery, and infantry soldiers in action and in camp. Battle scenarios, music, symposia, and medical, military, and civilian demonstrations are scheduled everyday. Fundraising raffles, merchants, and food vendors onsite. Virginia is for History Lovers!

More details for the 160th Anniversary commemorative events will be shared soon!

The Cedar Creek Battlefield Foundation is an entirely private 501c3 nonprofit dedicated to the preservation of the resources and lands related to the 1864 Battle of Cedar Creek. All proceeds from this event support our mission.

Leaf Peeping!!!

All Fall

As autumn is about to cast its golden spell over the landscapes of Middletown, Virginia, there's no better place to experience the enchanting beauty of leaf peeping than the Historic Wayside Inn. Nestled in the heart of this picturesque region, the Inn offers a captivating retreat where you can immerse yourself in the kaleidoscope of colors that paint the countryside. Wake up to crisp mornings, enjoy the Inn's 19th-century decor, and savor a hearty meal in our tavern. With its timeless charm and rich history, the Wayside Inn provides the perfect backdrop for a leaf peeping getaway that will “LEAF” you with memories as vibrant as the foliage itself.