5 Things To Know And Love About Shepherdstown, West Virginia's Oldest Town

Artist Deb Dickinson at Dickinson and Wait Craft Gallery creates artsy-fun clocks from old vinyl records—and that's about the only moment you'll think about time in Shepherdstown, West Virginia. Except to wish you had more of it. 

So jump in. Shepherdstown, the state's oldest town, trades more on active experiences than long-ago history (though the Colonel Revival and Federal style architecture is a heritage reminder at every glance). It's a college town—Shepherd University has been around since 1861—and the energy translates. The marathon option in October's Freedom Run, for instance, starts in neighboring Harpers Ferry, follows the Potomac River, touches on Antietam Battlefield, and lands on campus in time to cheer on the Rams, Shepherdstown University's powerhouse football team. 

Stay Outdoors

Shepherdstown is a C&O Canal town which means the towpath founded in 1831 to transport coal considers Lock 38, Mile Marker 72 a fitting place to stop—or start—your part of the 185-mile journey.  If you're ambitious, begin up in Georgetown (Washington, D.C., is under an hour away by car). Or work backward from the trail's other end in Cumberland, Maryland. Better still, launch your fun in Shepherdstown by turning to Eddie at Shepherdstown Pedal & Paddle—he'll outfit you with a kayak, canoe, boat, bike, or maps to go it by foot. 

On the water, lushly bordered by greenery, travel at a simple meander. The entire towpath takes about 5 days but your Shepherdstown portion is a worthy sliver. After all, there's more to do here.

With seven parks, Shepherdstown offers hikes both difficult and deliriously easy. A favorite is the one-mile loop around Morgan's Grove Park with its 20 acres of trees, meadows, and children's playground. Slightly harder is nearby Northern Peaks Trail Loop at a challenging 6.1 miles. 

Do Some Local Shopping

For more exercise you could simply walk around town, especially if you consider shopping a major sport (we do). Deb the clockmaker at Dickinson and Wait, in business now for about 30 years, specializes in all things American-made—from jewelry to woodworking and beyond (an added bonus comes with the many West Virginia artists featured). Four Seasons is one of those bookshops where warm advice comes with the visit—just tell owner Kendra your favorite titles, and she'll take you to your next read. 

At German Street Coffee-Candlery sip and ponder the scents of tantalizing candles. Or which DeFluri's Fine Chocolate you'll choose (hint: the wine truffles are award winners and made in nearby Martinsburg). And whether to try J.Q. Dickinson's ramp salt, applewood smoked or heirloom, all mined from an ancient ocean lying beneath Malden, West Virginia.  

Poke your head in any art gallery—Shepherdstown has a bounty—to feel the creative vibe that pervades the town. 

Note That July Is Theater Month

The Contemporary American Theater Festival returns to Shepherd University in July with its 32nd season of introducing new works and starting topical conversations. Theater devotees from Washington, D.C., place this on their radar as do New Yorkers. A rotation of three to five plays—pushing boundaries, surging the medium forward—are meant to celebrate theater's possibilities. Some have leapt to New York stages while others have garnered awards; the festival itself has been regarded by the New York Times as "one of 50 essential festivals."

Dine Around Town

The sons of Erwin and Carol Asam, founders of the much-lauded Bavarian Inn, have done what next generations do. They've take a great thing and made it better. The part German (strudel and sauerbraten), part Appalachian (local fish and wild game) menu has added such delights as the German sausage sampler. The added onsite brewery features Erwin's Angry Ale as a nod to dad. And an infinity pool sweeps your eye toward the Potomac River as you sit (or dine) at the accompanying bar. Several dining rooms take you from sit-down to casual; fire pits glow into Bavarian Inn nights. Stop by to eat or check in to sleep—73 rooms await. 

Other food opps include The Press Room for its martinis and oyster stew and Lilah's, a dog friendly spot for farm to table fare under pressed tin ceilings. If it's a mere nibble you're after, Mountaineer Popcorn's flavors range from birthday cake to dill pickle, caramel cashew to sriracha and honey mustard—a sealed bag lasts two weeks but good luck keeping it sealed. 

Book Your Stay

Shepherdstown offers true local stays with bed and breakfasts like The Thomas Shepherd Inn and Sun Dogs Bed & Breakfast. There's also Knott Cabin.

You'll go to sleep a visitor and awake feeling quite at home. That's the West Virginia way.