11 Most Charming Town Squares In Virginia
Winchester traded goods on its square for more than 250 years before anyone paved it. Middleburg still gathers on the block where the Red Fox Inn opened in 1728. Abingdon fills its square with theatergoers the way it has since 1933. These eleven Virginia squares still run the markets and stages they were built to hold.
Wytheville
In Southwest Virginia, Wytheville grew up along Main Street, part of the old Great Road that once carried settlers toward the western frontier. The historic downtown is easy to walk, lined with aging brick storefronts and historical markers, and a walking-tour brochure from the visitor center maps the older buildings. A few blocks hold much of the town's story. The Edith Bolling Wilson Birthplace Museum honors the Wytheville-born First Lady and second wife of President Woodrow Wilson. Just off Main Street, a 100-foot mural along the downtown Heritage Walk depicts scenes from her life, including her time in the White House.
The downtown mixes history with a little quirk. Snap a photo of the Big Pencil, a 30-foot yellow pencil that has hung above the Wytheville Office Supply store since the 1960s, then step into Skeeter's, a hot dog counter serving customers since 1925. For a closer look at the past, tour the Haller-Gibboney Rock House, an 1823 home built for the town's first resident physician. Come evening, catch live music or a movie at The Millwald, a theater dating to 1928 that also houses the Ghost Light Bourbon Bar.
Fredericksburg
On the banks of the Rappahannock River, just south of Washington, DC, Fredericksburg is a favorite for history buffs. With a history that stretches back to the eighteenth century, Fredericksburg was a key site in both the American Revolution and the United States Civil War. Today, visitors can learn about both at the Fredericksburg and Spotsylvania National Military Park, which offers "history at sunset" talks, self-guided tours, and visits to historic buildings that played roles in the Civil War.
Back in town, the town square is part of a National Historic District with hundreds of 18th- and 19th-century buildings, many of which now house shops and restaurants. Pop into Riverby Books for unique used and rare books, plus locally-made ceramics and gifts. Be sure to check out the Town Hall and Market Square, which was built in 1816 as a spot for municipal events and a farmer's market, and today houses a local history museum and hosts regular events, including concerts and artisan markets.
Middleburg
At the center of Virginia's horse country, Middleburg keeps a small, old-fashioned downtown, though it's far from frozen in time. The town square of "The Nation's Horse and Hunt Capital" is lined with historic buildings. One major landmark is the Red Fox Inn, established in 1728, whose twenty-two boutique rooms span multiple historic properties in the center of town, and which also has a pub, dining room, and wedding venue.
For something to take home, head to the nearby Middleburg Antique Gallery, where 45 traders sell antique furniture, art, and accessories under one historic roof. Afterward, grab a cone at Piedmont Drip and Dip, which serves ice cream and coffee in a town square spot once occupied by Scruffy's Ice Cream Parlor.
Culpeper
A short drive southwest of Washington, DC, Culpeper is a favorite among antique hunters. Its downtown sets historic architecture alongside a run of antique shops. Check out Vintage Vibes of Virginia, where a small shopfront holds solid wood antique furniture, sparkly vintage jewelry, and other treasures.
The Culpeper History Museum covers the area's history back to prehistoric times, and has also hosted family-friendly Wizard Weekend mini escape rooms. Afterward, enjoy a classic American meal at the Piedmont Steakhouse, which is housed in a historic building dating back to the 1890s, complete with pressed-tin ceilings.
Williamsburg
Famous for the living history attractions at Colonial Williamsburg, the town of Williamsburg wears its eighteenth-century history with pride, especially in the town square. Williamsburg's town square is Merchants Square, which features shops and restaurants in an 18th-century-style setting with limited car access.
Merchants Square is a typical first stop for anyone who's purchased tickets to Colonial Williamsburg, which include access to tours and demonstrations by costumed reenactors in the 18th-century recreated town. In the square itself, though, no tickets are necessary. Shop for sweet and salty snacks at the famous Peanut Shop of Williamsburg, which sells dozens of variations on roasted Virginia peanuts. Or, grab a locally-brewed beer at the DoG Street Pub, which, despite the fluffy friend on the sign, is actually named for its address on Duke of Gloucester Street.
Winchester
Although it underwent major renovations in 2013, the town square in Winchester has been a marketplace and town gathering spot for over 250 years. The heart of Winchester's historic Old Town, the town square is also part of a National Historic District. Visiting families can explore the Shenandoah Valley Discovery Museum, which features interactive, play-focused exhibits on the Valley's history and ecology, as well as a musical rooftop garden.
Have something to eat at the Village Square Restaurant, which hosts regular happy hours and Sunday brunch in a historic former auto shop. Or, try the Piccadilly Public House, where there's free live music every weekend to go with your food and drinks in this converted historic warehouse space.
Charlottesville
Home of the Cavaliers, Charlottesville is famous for the University of Virginia, founded by Thomas Jefferson, who lived nearby. His former home, Monticello, is now one of Charlottesville's most popular tourist attractions, where visitors can tour the house and grounds and learn about the lives of those, both free and enslaved, who lived there.
In the heart of Charlottesville, the town square, known as the Historic Charlottesville Downtown Mall, features over 100 shops and restaurants along a single brick-paved stretch. Catch a concert at the Jefferson Theater, which opened in 1912 and now showcases local bands and major acts. Grab a traditional Southern meal like fried chicken and greens or blackened catfish at The Whiskey Jar, which also hosts the Whiskey Society of Central Virginia and stocks a large whiskey selection.
Abingdon
In the Blue Ridge Mountains of southwest Virginia, Abingdon centers on a walkable 20-square-block historic district along Main Street. Brick sidewalks connect Federal and antebellum buildings, and much of the downtown is listed on the National Register of Historic Places. Two of its best-known landmarks face each other across Main Street: the Martha Washington Inn and Spa, a 19th-century former women's college that now runs as a hotel and spa, and the Barter Theatre, which has staged shows since 1933 and takes its name from a Depression-era policy that let patrons trade produce for tickets.
Beyond the inn and the theater, the district rewards a slow walk. Stop by the Arts Depot, a restored 1870 railroad station where artists work in open studios, or the William King Museum of Art, set in a former 1913 school. The 1868 Washington County Courthouse still presides over the town center, and a self-guided walking tour map from the visitor center highlights the oldest buildings, including The Tavern, Abingdon's oldest structure. When you want to trade the streets for the trees, the Virginia Creeper Trail begins nearby and runs 34 miles through the surrounding mountains.
Onancock
Founded in 1680, Onancock is one of the oldest towns on Virginia's Eastern Shore and served as Accomack County's first seat. Its downtown follows Market Street, where brick and clapboard storefronts hold shops, galleries, and restaurants within a few walkable blocks of Onancock Creek. Many of the buildings went up after a 1900 fire, giving the street a consistent turn-of-the-century look. On the second Friday of each month, the galleries stay open late for an art stroll, and on Saturday mornings in season, the Onancock Market draws local farmers, watermen, and makers into the town center.
Market Street also sets up the rest of the visit. Browse folk and landscape work at galleries like Crockett Gallery and the Danny Doughty Gallery, then catch a film at the historic Roseland Theater, which has shown movies since the 1950s. The town's public murals pay tribute to its long history, and the Foggy Place Cafe serves breakfast, lunch, and specialty drinks surrounded by work from local artists. From the harbor a few blocks away, the seasonal Tangier Island Ferry carries visitors out onto the Chesapeake Bay, and the Colonial Manor Inn offers rooms in a former private home close to the water.
Occoquan
On the banks of the Occoquan River just south of Washington, DC, Occoquan is a small riverside town built around its old town square. Visitors should head to the nineteenth-century Historic District and town center, which are home to the Occoquan Historical Society and the Mill House Museum. The museum displays over 400 items related to Occoquan's history, all within a well-preserved eighteenth-century mill.
Continue the culture fix at The Loft Gallery. This waterfront fine arts gallery houses works from 22 local artists. After enjoying the art, try a meal at Madigan's Waterfront. This riverside restaurant specializes in fresh seafood, but also offers steaks and a weekend-only brunch menu.
The Plains
The Great Plains lie far to the west of Virginia, but the town of The Plains sits just an hour's drive from Washington, DC. A highly affluent small town in Fauquier County, The Plains has a town square lined with shops and restaurants. Pop into Youngblood Art Studio to see work by local artists or commission a piece of your own. The studio also offers art therapy.
Browse Baileywyck Antiques, a large gallery of upscale antique furniture and homewares. Grab a meal at the Railstop Restaurant, which has been offering eclectic New American cuisine for three decades, and be sure to catch a look at the toy train running through the restaurant.
The Squares That Keep Virginia's Small Towns Moving
Virginia lives up to its "Virginia is for Lovers" slogan, and its small-town squares are a big part of the draw. You can browse antiques in Culpeper, catch free live music in Winchester, or grab a bag of roasted peanuts in Williamsburg's Merchants Square. Fredericksburg's Market Square has hosted municipal events and farmers since 1816, and it still does today.
