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Winchester and Frederick County, Virginia at the top of the Shenandoah Valley, was once Shawnee camping grounds to which Pennsylvania Quakers came to settle in 1732.

Winchester has long been known as the “Apple Capital” surrounded as it is by vast orchards and constituting one of the largest apple export markets of the nation and the largest producing area in Virginia. Each spring Winchester plays host for four days to over 250,000 visitors who converge upon the town to witness the famous Shenandoah Apple Blossom Festival, usually held the first few days in May. East of Winchester, you’ll find Loudoun, recognized for its location in the wine country of Washington, DC.

Harpers Ferry, West Virginia is a historic community at the confluence of the Potomac and Shenandoah Rivers where the U.S. states of Maryland, Virginia and West Virginia meet. Best known for abolitionist John Brown’s raid on the Armory in 1859 and its role in the American Civil War, the lower part of town is located within Harpers Ferry National Historical Park. Most of the remainder, which includes the more highly populated area, is included in the separate Harpers Ferry Historic District. The Appalachian Trail Conservancy, the organization tasked with managing and preserving the AT, maintains its headquarters here.

There are numerous sites related to this area’s significance in both the Revolutionary and Civil Wars including George Washington’s headquarters, the headquarters of Stonewall Jackson, houses of the Revolutionary era, the National Cemetery and many more.

Shenandoah County, in northwestern Virginia, is home to six towns: Strasburg, Toms Brook, Woodstock, Edinburg, Mount Jackson, and New Market. The county includes the communities of Fort Valley and Orkney Springs/Bryce. Shenandoah County is 35 miles long, 10 miles wide, and home to the famous seven bends of the Shenandoah River, the Meems Bottom covered bridge, and the George Washington National Forest. Popular attraction Shenandoah Caverns has been welcoming visitors from around the world since it opened in 1922. The Fort Valley and western slopes of the Massanutten Mountain are located within the county.

Stories from Winchester, Harpers Ferry, & Shenandoah

September 16, 2021
Virginia's creative and sometimes whimsical LOVEworks are a wonderful photo opportunity. Why not start a new tradition and make some family memories finding and photographing a few LOVE signs while enjoying the out of doors this year?
February 24, 2021
A drive along the scenic Blue Ridge Parkway is literally a trip through time. Construction on the Parkway began near Cumberland Knob in North Carolina in September 1935. Works Project Administration crews completed some of the early road construction, landscaping and recreation area development. As you travel the Parkway today,…
January 25, 2021
January 26 is National Plan for Vacation Day and I’m including my tips for vacation planning amidst the unpredictability of 2021. My husband and I have sadly been planning back-to-back transatlantic and Mediterranean cruises for more than a year that have just been canceled. But, we’re still healthy and still…
October 14, 2020
Fall color season is upon us and the hillsides are dotted with the reds of maples, sourwoods and sumac and the yellows of birches and yellow poplars. But even after the trees are bare, these routes offer sites worth visiting- they promise to tickle your taste buds, enthrall your eyes…
September 9, 2020
Enjoy waterfalls and cascades throughout Shenandoah National Park, the Blue Ridge Parkway, and the Great Smoky Mountains National Park!
August 26, 2020
The Blue Ridge Mountains are dotted with farms producing everything from Christmas trees to trout. Fruit, flowers, herbs, jams, jellies, pies, wreaths and other crafts are all produced right here in the mountains.
March 22, 2019
As the weather warms, spring fever leads many of us outside and to planning some trips. Whether an impromptu weekend getaway or looking ahead to what's happening later this season, there's no shortage of fun activities in the regions near the Parkway in spring. Read on for our break down of what's going on this season in each region of the Blue Ridge Parkway.
November 18, 2018
Spending the holidays in the Blue Ridge Mountains brings to mind cozy fireside nights under homespun quilts, a brisk family hike to find the perfect Christmas tree on the farm, and the very the best slopes for skiing and sledding. We’ve rounded up all this and more in our guide to festive winter fun in the communities along the Blue Ridge Parkway.

Recommended Itineraries

Region: Virginia
Duration:1 day
Do you remember the choose-your-own adventure books from your childhood? The ones where you got to select the event that happened next in the story and then turn to the corresponding page in the book? Well, here are three options for you to choose your own one-day adventure in Shenandoah…
Region: Virginia
Duration:2 - 3 days
A two-night stay is all it takes to feel rejuvenated. This itinerary in Shenandoah County, VA even takes the stress out of planning the trip.