Family Fun Activities in Winchester
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Winchester Area

The Heart of the Virginia Kids Trail

The Winchester area is the heart of the Kids Trail. In town, you’ll find walking tours and nature trails along with a terrific children’s museum. Once you’ve covered Winchester, take the family to nearby Clarke County. Or head down the interstate to Stephens City, Middletown, Front Royal, and Shenandoah County. I-81 makes area attractions minutes away.

Stops to Make in Winchester

Downtown Winchester offers several historical walking tours. For instance, did you know George Washington had a surveyor’s office in town? Civil War General Stonewall Jackson also made his headquarters here. The town also has a pedestrian mall. You’ll find shops, restaurants, and entertainment while hotel accommodations are steps away.

Explore at Shenandoah Valley Discovery MuseumStart the morning at Abrams Creek Wetlands Preserve. Over 180 kinds of birds call it home. Afterward, visit Handley Regional Library. The building looks like an open book. And across the street, there’s Shenandoah Valley Discovery Museum. Complete your trip with a stop at West Oaks Farm Market’s community store. Bring home fresh produce as well as goodies from local food artisans.

Other Winchester Area Kids Trail Stops

Next door to Winchester is Clarke County. Pick your own fruits and vegetables at Mackintosh Fruit Farm. The State Arboretum is also nearby. And don’t forget to stop by that Virginia classic Dinosaur Land. Step into the prehistoric past!

Sky Meadows State Park Winchester Area VA Kids TrailBordering Clarke and Fauquier counties are Sky Meadows State Park. Visit the Children’s Discovery Area before walking the Sensory Explorers’ Trail. It’s designed for all park visitors, including visually, hearing, and mobility impaired. And since the park hosts astronomy events, Sky Meadows is an ideal location for stargazing.

After Clarke County, you can continue east to the Kids Trail Leesburg region. Or head south to more Winchester area destinations.

Winchester Area Nearby Neighbors

Family Drive In Winchester Area VA Kids TrailStephens City: Once called Newtown, this is the second oldest Shenandoah Valley town. After touring the historic district, head over to Sherando Park. Play some disc golf and fish at the lake. Enjoy a picnic supper, then make it a night at a drive-in movie.

Middletown: This area was a major backdrop for the Civil War, so Middletown changed hands many times. In fact, the armies agreed not to burn down the local inn because they knew they would need it again during the next advance. The Cedar Creek Junior Ranger Program gets kids interested and involved in history and national parks.

Front Royal: This town is known as the Gateway to Shenandoah National Park. It’s also regarded as Virginia’s “Canoe Capital” because of the famous Shenandoah River. Ten miles south of town, put in at Shenandoah River State Park. 

Shenandoah County Destinations

Family play at Skyline PaintballWhile recognized for its grassroots art culture and Civil War history, Strasburg is also home to Skyline Paintball. Open weekends, even children as young as seven can play with low impact ammo.

Splatting not your style? Then take a 15-minute ride over to Elizabeth Furnace Campground near Woodstock and check out the swinging bridges. Or climb Woodstock Tower and take in the 360-degree view. After the tower, do some hiking at Seven Bends State Park.

Looking for more fun on this part of the Kids Trail? Make a stop at Shenandoah Valley Cultural Museum in Edinburg. Then check out Meems Bottom Covered Bridge in Mt. Jackson. It’s the longest one in Virginia. And before you head into the KT Harrisonburg region, stop by Shenandoah Caverns. See natural wonders and tour a collection of 20 parade floats.

Because you can measure travel by minutes instead of miles, try a Kids Trail tour based on family interests. And don’t forget to include some of this free fun.

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