Winchester’s Spring Fling

Home » What's New » Winchester’s Spring Fling
Shenandoah Apple Blossom Festival

The Shenandoah Valley is usually associated with natural scenic beauty, quiet mountain getaways and idyllic trips along a trail or down a river. But every year about this time, the Shenandoah Apple Blossom Festival in Winchester turns the Valley into something else entirely. 

The 94th Shenandoah Apple Blossom Festival will be held April 23 – May 2, is more than 20 events, many of them ideal for family fun. Festival fans need to understand that they are working under a new set of rules with temporary changes in 2021. Current statewide restrictions on indoor and outdoor gatherings limit the Festival’s ability to plan major events like parades and the Midway in Old Town Winchester.  Large scale indoor events will transition outdoors under multiple tents at the Frederick County Fairgrounds.  Events include live music, dances, wine and cider tastings, along with the Apple Blossom Carnival offering a variety of activities for the entire family (Find a more complete schedule here.) Over 90 years, it has earned a variety of awards from Fordor’s Travel, the American Bus Association, USA Today and many other outlets. 

Winchester is located in the northern end of the Valley, about 70 miles northwest of Washington, DC. Even if you can’t make the Apple Blossom Festival, there is still a great deal to see and do.
Some highlights: 

Stroll the walking mall in Historic Old Town and discover specialty retail shops of all kinds, and find almost any type of dining in the many outdoor cafes and restaurants. Violino Ristorante Italiano, on North Loudoun St. is highly recommended.  

Now through October 31, visit the Museum of the Shenandoah Valley to see a  fascinating fiber art exhibition – Rock, Paper, Scissors – which presents contemporary textiles and mixed-media works created by artists from New Image, an all-female group of active studio artists from Virginia, Maryland, and Washington, DC, who work primarily with cloth, paper, and alternative materials. Inspired by the natural landscape of the Shenandoah Valley and the materials used by New Image artists, Rock, Paper, Scissors presents a wide range of art, from standard quilts to three-dimensional works. All works will be on first-time public view at the MSV. On view until October 31, 2021. Rock, Paper, Scissors is organized and curated by Shenandoah Valley resident Trudi Van Dyke. 

Just outside Winchester in Stephens City (the second oldest town in the Valley) you’ll find the Newtown History Center, one of many small Valley museums devoted to a local area. Here you will see displays or Stephens City craftsmen, Civil War history, and town history. Please check their website for current days and hours of operations before your visit. 

The Shenandoah Summer Music Theater announced that they will be featuring one title production this summer.  The production will run an extended period of 37 performances between July l through August 1, 2021. The show title was recently announced so check online for updates. 

In Middletown, a bit south of Winchester, is the historic Belle Grove Plantation. On Saturday, April 10 you can volunteer at the Civil War Trust’s annual hands-on event to help battlefields and historic sites across the country. Volunteers are needed for fence repair and painting. If you are interested, visit here to register.   

Need lodging? The George Washington A Wyndham Grand  Hotel should be high on your list of options. 

Start your visit to Winchester at the Winchester-Frederick County Visitors Center, at 1400 South Pleasant Valley Road. 

Photo courtesy Renee Bayliss, Winchester-Frederick County Convention and Visitor Bureau 

Stay Updated

Get the latest events and things to do through our monthly e-newsletter.

Stay Updated

Get the latest events and things to do through our monthly e-newsletter.

Stay Updated

Get the latest events and things to do through our monthly e-newsletter.




Meetings & Travel Trade


Deals & Specials

Press Room

Film Industry

Contact Us

International Visitors

Stay Updated

Get the latest events and things to do through our monthly e-newsletter.