Winchester Region

The Heart of the Virginia Kids Trail

Build your travel experience around Winchester, the heart of the Kids Trail. Downtown offers several historical walking tours. For instance, did you know that George Washington had a surveyor’s office in town? Or that Civil War General Stonewall Jackson made his headquarters here? Downtown Winchester also features a pedestrian mall with retail, dining, and entertainment with hotel accommodations steps away. You’ll also find seasonal live theater, with kid friendly performances,  produced by Shenandoah University. And just minutes from downtown, you can visit farmers markets and food artisans.

Continue your trek through the heart of the trail in Stephens City. The Newtown Heritage Festival is an annual family friendly celebration promoting the town’s heritage and civic pride. And if you’re looking for some 20th century history, take in retro drive-in movie experience. 

Farther down the Trail you’ll find Middletown. During the Civil War, Middletown changed hands so many times that opposing armies agreed not to burn down the historic 1797 Wayside Inn after each retreat because they expected to need it again during the next advance.

Middletown’s next door neighbor is Front Royal. The town is known as the Gateway to the Shenandoah National Park. And with two forks of the famous Shenandoah River, Front Royal is also regarded as the “Canoe Capital” of Virginia.

Heading south from Front Royal, you’ll enter scenic Shenandoah County with the towns of Strasburg and Woodstock. Recognized for its grassroots art culture, pottery, antiques, and Civil War history, Strasburg is also home to an eclectic museum with a working railroad model and red caboose you can tour. And while Woodstock may be small in size, it’s big on festivals. Plus, it’s centrally located on the annual Rt. 11 Yard Crawl - a 43 mile bargain trail. 

Enjoy your stay in the Winchester region while spending time with our Kids Trail partners. Below scroll down to see this area’s partners and use the drop down menu to sort them by your child’s interests.

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