Between Greensboro And Richmond Is A Small Town With Historic Charm, Sporty Appeal, And A Walkable Downtown

Virginia is a state with profound historical significance, and spots like Williamsburg, one of America's first planned cities, and Yorktown are among its most relevant spots. However, there are also a number of smaller places across The Old Dominion that are rife with archaic charm. One such locale is a town between Richmond, Virginia, and Greensboro, North Carolina, with the somewhat surprising name of South Boston. Visitors to this memorably named town will find it has a walkable downtown that's home to a variety of shops and restaurants, as well as sporty appeal that juxtaposes its old-world feel.

Naturally, the name "Boston" calls to mind the Massachusetts city that was integral to the colonies' success during the Revolutionary War. When the leaders of a relatively young community in Southern Virginia applied to get a post office for their town in the late 1800s, they, too, wished to be called Boston. However, that request was denied — not because Boston already existed in Massachusetts, but because there was already a city named Boston in Virginia. South Boston thus became the town's official name.

Today, a number of buildings remain from the original townsite; having stood for well over a century, they lend significance to the city's landscape. You can take a walking tour of the late Victorian Italianate and Neoclassical-style architecture, including locales like the old Glasscock Hardware building and the former Planters and Merchants Bank building, the latter of which is now occupied by a used furniture store. The majority of the buildings downtown are still in use. The tour also brings attendees to the doorsteps of over a dozen historic homes in varying architectural styles, including Carpenter Gothic, Queen Anne, Greek Revival, and more.

Many of the town's historic buildings are located downtown. With dozens of businesses on the strip, including a variety of shops, boutiques, restaurants, and breweries, South Boston's downtown core is highly walkable. It's little surprise that antique and vintage shopping can be found here — much like in the nearby town of Altavista, which offers vintage charm and prime antiquing alike. One hotspot in South Boston is Sullivan's Antiques, which occupies one of the buildings on the walking tour. At Sullivan's you can find goods ranging from antique furniture to salvage architectural components. Walking us a couple blocks up the street brings you to The Mercantile and Vintage Market. There you'll find an array of both new and vintage furnishings, accessories, and decor. 

There are also ample dining options located along historic Main Street and Downtown District. Among those are the quaint bistro Southern Plenty and Main Street Bar & Grill. The Downtown South Boston Farmers Market is another attraction that's popular with locals and visitors alike. This weekly market features locally grown produce, plus a variety of homemade products produced by area artisans. You can catch the Farmers Market on Saturdays from April to October and on Wednesdays from May to August.

While there are several modern hotels in town, visitors can also enjoy South Boston's historic charm at their overnight accommodations. One such option is the Charles Bass House Bed & Breakfast, which is among the stops made on the walking tour of the South Boston Historic District. If you're comfortable staying a little ways west of downtown, you could try booking a room at the popular Berry Hill Resort, which has been accommodating guests for nearly 300 years.

Although South Boston is rich in history, it also has quite the sporty side. You can get your adrenaline up by watching a race at the South Boston Speedway, which lies just east of town. Over the past seven decades, the speedway has held a variety of events, including NASCAR races. During a typical season, the South Boston Speedway hosts over a dozen races from spring through fall. Visitors can even do a bit of driving themselves at World of Sports, an entertainment center that offers go-karting and bumper car driving, alongside bowling, axe throwing, and laser tag.

Outdoor sporting enthusiasts can hike along the South Boston section of the Tobacco Heritage Trail, which begins just a few minutes away from the downtown core. This path covers a little over 5 miles of terrain out and back. Along the way, it winds through a variety of historic sites and landmarks, as well as wooded areas filled with wildlife — notably, well over a dozen bird species have been spotted along this trail.

Whether you're heading to South Boston to enjoy historic charm, downtown shopping, or sports-based excitement, getting there from nearby cities is simple enough. Although South Boston is in Virginia, it's closer to Durham, North Carolina — aka "America's Drinking Capital" — than it is to any major city in its own state. Consequently, North Carolina's Raleigh-Durham Airport (RDU) is also the closest major airport. If you're headed to South Boston from Durham, simply drive straight up the US-501 for a little over 50 miles.