Discover a Historic Town with Unique Shops and Scenic Trails in the Heart of Virginia’s Shenandoah Valley

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Discover a Historic Town with Unique Shops and Scenic Trails in the Heart of Virginia's Shenandoah Valley

Virginia’s Shenandoah Valley is home to some of the most scenic locations in the state. The Skyline Drive along the Blue Ridge Parkway offers Virginia’s best fall drive with Appalachian Mountain views while Shenandoah National Park features accessible views of Virginia’s green paradise. Hidden in the heart of the valley is a historic town that offers a bevy of unique shopping opportunities and scenic trails. 



Founded in 1761 and named by George Washington, Woodstock, Virginia, is one of the oldest towns in the Shenandoah Valley. It has served as the county seat for over 250 years, was the site of several Civil War battles, and today is a thriving town filled with locally owned restaurants, artisans, mountain views, and plenty of outdoor recreation for all skill levels.

Woodstock is exceptionally easy to get to thanks to its proximity to Washington, D.C., and other Shenandoah Valley travel spots. It’s an hour and 15 minute drive westward from Washington Dulles International Airport and only 40 minutes south from Winchester Regional Airport. For roadtrippers, Woodstock has exits off U.S. Route 81, which is the central highway through the Shenandoah Valley. So, if you’re looking for a wonderfully relaxing place to visit that’s brimming with historic charm and outdoor scenery, Woodstock is the place to be.



Shenandoah Valley scenery makes Woodstock an outdoor paradise

Woodstock sits in the middle of the Shenandoah Valley, which is easily one of the most scenically beautiful locations in the United States. The mighty Shenandoah River winds its way through the landscape like a watery snake, and there is no better place in Woodstock to experience the river and woods than Seven Bends State Park. The spot makes for easy hiking and productive fishing on the North Fork of the Shenandoah.

Experienced mountain bikers will love the Talus Trail, a black diamond ridge that drops nearly 2,800 feet. Hikers looking for a challenge can take the Woodstock Lookout Trail, a 13-mile uphill hike across the Reservoir, Talus, and Massanutten trails. It’s quite a hike (pun intended) but it is more than worth the effort for the stunning views of the gorgeous Shenandoah Valley that await.

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No matter where you go in Shenandoah Valley, whether it’s Lexington with its local flavors and endless outdoor adventures, or the underrated, but charming Fort Royal, you can be guaranteed endless amounts of wonderful adventures that will have you returning again and again.

Woodstock is a town for history buffs

Woodstock offers unique shopping for everyone

While the history buffs are taking in the historic sights of Woodstock, more modern-minded visitors are taking advantage of the unique shopping opportunities offered by the town. Woodstock is a prime location to sample the abundance of Shenandoah Valley farmers. The South Street Barn Market houses a year-round Saturday farmers market that brings together farmers and craftsmen from around the region. Sample local apples, fresh baked goods, chocolates, all-natural beauty products, artwork, and other local crafts. Mowery Orchard Farm Market on Route 42 is another great spot to sample the local flavor, especially if you’re looking for provisions before a day of adventuring. 

A quick stroll down Main Street provides ample chances to shop at local boutiques. Shop Three French Hens for unique jewelry, antiques, and furniture; The Butter Cup for women’s clothing, pottery, and candles; and Traveler’s Treasures for Virginia souvenirs, apparel, and local arts and crafts. Art lovers will enjoy The Shenandoah Museum of Contemporary Art for its display of local painters and sculptors. A stop at the Art Spot for paint-your-own pottery classes makes for a great date or family night.

Dave Pennells

By Dave Pennells

Dave Pennells, MS, has contributed his expertise as a career consultant and training specialist across various fields for over 15 years. At City University of Seattle, he offers personal career counseling and conducts workshops focused on practical job search techniques, resume creation, and interview skills. With a Master of Science in Counseling, Pennells specializes in career consulting, conducting career assessments, guiding career transitions, and providing outplacement services. Her professional experience spans multiple sectors, including banking, retail, airlines, non-profit organizations, and the aerospace industry. Additionally, since 2001, he has been actively involved with the Career Development Association of Australia.