All photos by Bryan Dearsley / LuxuryVirginia
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As anyone who has had the good fortune to travel through the Shenandoah Valley will tell you, there’s something so very special about this beautiful part of Virginia. For me, it’s the fact that this magnificent 140-mile stretch of my new favorite state made for one of the best road trips I’d ever undertaken (and I’ve been on a lot!).
Stretching from Winchester at the north end of “The Big Valley” all the way south to Waynesboro, there’s certainly no shortage of scenic eye candy along the way. That said, for me the highlight was having the chance to get to know these and a few of the region’s other wonderful small towns.
Find out more with these tips and tactics for a memorable getaway to some of the very best small towns in Shenandoah Valley.
The Best Small Towns in Shenandoah Valley
Lovely Lexington
The lovely town of Lexington brings together history, scenic surroundings, and a long-standing appreciation for all things equestrian. Park your car near the Visitor Center of Lexington (metered street parking as well as a parking concourse are close by) and pop in for some local tips from the helpful staff there. If you’re planning on a carriage ride (heck, you should!), it’s here you’ll be picked up from the Lexington carriage Company.
Downtown Lexington is a great place to shop, but be sure to allocate time to walk just a little beyond Main Street to the grounds of Washington and Lee University (W&L). A campus highlight is the University Chapel and Galleries, situated in the heart of the W&A Historic District and home to an interesting museum. This beautiful college green space stretches to the neighboring Virginia Military Institute (VMI), a 19th century military college with an excellent museum. Another must-see historic site is Stonewall Jackson House, which gives insight into the life of the famous Civil War general who once lived in town.
Take a short drive south of Lexington and you’ll arrive at the spectacular Natural Bridge State Park. This massive limestone arch has been a point of fascination for generations, and a riverside trail will have you standing directly beneath this spectacular natural phenomenon. And just to the north of town, the Virginia Horse Center regularly hosts equestrian events and can be toured.
If you fancy a boutique-style stay in the core of Lexington, check out The Georges. Named in honor of two famous Georges that were integral to local history (Washington and Marshall), this charming 4-star inn blends old-world ambience with modern touches. For dinner, Haywood’s Restaurant offers dishes informed by Southern tradition, frequently accompanied by live music. If you prefer a casual night out, Heliotrope Brewery is the spot to kick back with a pizza and a craft beer.
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Bryan Dearsley is Editor of LuxuryVirginia, and a huge fan of the “Old Dominion.” He’s also Co-Founder of Riley and its luxury lifestyle websites, leading sources of news and reviews relating to luxury lifetyles and travel around the world, including the UK, Europe, and the United States.
