Winchester, VA: The Shenandoah Valley's Gateway to Family Fun

by Micaela Williamson

Situated in the northern portion of Virginia's Shenandoah Valley, the City of Winchester is a destination for all seasons. Winchester hosts its signature, huge Shenandoah Apple Blossom Festival in the spring and a festive Christmas Parade and Tree Lighting in December.  But, throughout the year the city is rich in history, shopping, dining and plenty of attractions for the whole family. 

What to see:

Shenandoah Valley Discovery Museum
19 W. Cork St.
Winchester, VA 22601

This discovery museum for all children is packed with tons of hands-on exhibits focusing on the arts, science, pretend play, math, engineering, history and more.  The museum also hosts lots of special programs and events for families too. Parents are encouraged to learn, create and explore alongside their children.  Don't miss signature exhibits like creating tracks in Roller Coaster Alley, pretending to be an EMT in the life-sized ambulance, stepping inside a Powhatan home on the Moccasin Trail, getting a bird's eye view of the city from the Observation Deck and much, much more!  

Patsy Cline Historic House
608 S. Kent Street
Winchester, VA 22601

Country music fans can get a glimpse into the life of one of Winchester's most famous residents, Patsy Cline.  From April- October, 45 minute guided tours are offered for a small fee. There is also a gift shop on site with unique Patsy Cline memorabilia. 

Museum of the Shenandoah Valley
901 Amherst Street
Winchester, VA 22601

A great museum with a fantastic art collection, the interesting Glen Burnie Historic House, and breathtaking gardens. Kids will marvel at the R. Lee Taylor Miniatures Collection, and history buffs can learn about the Shenandoah Valley region's rich past through artifacts, artwork and documents. 

Family Drive-In Theatre
5890 Valley Pike (US Rt. 11-South)
Stephens City, VA 22655 

This is the closest drive-in theatre to the Washington DC region and shows a variety of nostalgic films, cult classics and many popular new releases. It is open most of the year,  has many special events and is a great place for old-fashioned family fun!

Winchester-Fredrick Historical Society Museums

Check out Winchester's important contributions to our nations' history at one of the five museums maintained by the Winchester-Fredrick Historical Society: Abram's Delight, George Washington's Office, Stonewall Jackson's Headquarters, an 18th Century Valley Cabin and the Hollingsworth Mill. Those visiting may purchase a block ticket for admission to Abram's Delight, Stonewall Jackson's Headquarters or George Washington's Office.  The 18th Century Valley Cabin is included with Abram's Delight and admission to Hollingsworth Mill is free. 

Where to eat and shop:

The downtown mall or Loudoun Street Mall in Old Town Winchester is packed with many great restaurants and shops.  Its an attraction within itself.  No matter what your taste is, there is cuisine for everyone.  

Where to stay:

The George Washington Hotel
103 East Piccadilly Street
Winchester, VA 

This is hands-down the best place to stay in Old Town Winchester. Is location is walking distance to the downtown area pedestrian mall and many attractions. Plus, the luscious, Roman spa-like indoor pool is a favorite for families. On-site dining includes breakfast, lunch, and dinner at the Dancing Goat restaurant and if you can slip away, the cocktail menu at the gorgeous Half Note Lounge is to die for!  Choose between standard king and queen rooms or posh suites for an unforgettable stay. 


For more suggestions of family-friendly fun in the Shenandoah Valley Region, check out the Shenandoah Valley Kids Trail.



Disclosure: I was invited on a media trip with the Virginia Tourism Corporation and Shenandoah Valley Kids' Trail and experienced many of these attractions for free. No other compensation was given.  All opinions are my own, and I adore Old Town Winchester as a great place for family fun.