10 Prettiest Downtown Strips In Virginia
Main Street Culpeper is set against the Blue Ridge Mountains and lined with colorful murals. Staunton's Beverley Historic District sits in the Shenandoah Valley, where you can catch a performance at the iconic Blackfriars Playhouse. On the Chesapeake Bay, Cape Charles offers a day at the beach and waterfront dining to toast the sunset. Each of these fetching downtown strips showcases a different side of Virginia.
Staunton
Located in the lush lowlands of the Shenandoah Valley sits the town of Staunton. Staunton's main drag, the Beverley Historic District, boasts alluring Victorian architecture, as well as a myriad of locally owned shops and restaurants such as Staunton Books & Tea and farm-to-table eatery Zynodoa. Set between the Blue Ridge and Allegheny Mountains, Staunton is a small town rich in scenic beauty. Downtown hosts popular events such as the Staunton Music Festival, where classical music lovers rejoice, and it also offers historic attractions such as the Woodrow Wilson Presidential Library and Museum, and the captivating American Shakespeare Center's Blackfriars Playhouse, the world's only recreation of Shakespeare's original indoor theater.
Culpeper
Just an hour from D.C. and set in the foothills of the Blue Ridge Mountains, Culpeper's beautiful downtown strip revolves around the historic district, where preserved 19th-century storefronts line the street. Main Street is home to several alluring boutiques, cafes, and antique shops, as well as the beautifully restored State Theatre. Capture memories on the photo-worthy Culpeper Mural Tour featuring one-of-a-kind works by local artists that adorn downtown with color. Or take in the natural splendor at Wine Street Memorial Park and Lake Culpeper, where locals enjoy boating and fishing.
Downtown is also home to the Museum of Culpeper History, located at the historic train depot. This small facility houses a vast number of historical artifacts, ranging across dinosaur bones, modern art and more. At the heart of Culpeper stands East Davis Street, a colorful strip lined with revitalized shops and restaurants. Explore independently owned boutiques such as Eye of the Beholder, which features a selection of local artisan products, and the apparel and print shop Le Monkey House.
Abingdon
Brick sidewalks decorate the 20-square-block Historic District in downtown Abingdon, along with an assortment of enticing eateries and cultural landmarks. Witness the well-preserved beauty of the Barter Theater. Established during the Great Depression, it continues to host a bevy of stage productions year-round, as well as the annual Appalachian Festival of Plays & Playwrights.
Downtown Abingdon is also home to the Arts Depot, a historic railroad station that has been transformed into art galleries and studios, and the William King Museum of Art is a few blocks away. Community members head downtown for the Abingdon Farmers Market to shop from a colorful assortment of local vendors. Additionally, the Virginia Creeper Trail begins near the historic district and offers miles of mountain views along expansive hiking and biking trails.
Lexington
Just two hours west of Richmond and set in the Shenandoah Valley, downtown Lexington is a fine day-trip destination. Lined with red brick sidewalks, Main and Washington Street are noted for their walkability. Admire the historic architecture at sites like the Jackson House Museum, the preserved home of Thomas "Stonewall" Jackson. Or visit the Virginia Military Institute, which features well-kept grounds and roughly 20,000 military artifacts on display.
Those interested in a guided tour can take a horse-drawn journey through town with the Lexington Carriage Company, and anyone looking to enjoy Lexington's natural scenery is welcome to explore one of the many hiking and biking trails accessible from downtown, such as the Woods Creek Trail and the Back Campus Trail located on the Washington & Lee University campus.
Middleburg
Established in 1787 and set against the Blue Ridge Mountains, Middleburg's downtown strip reflects Virginia's horse and hunt country. With well-maintained stone buildings, acres of surrounding horse farms, and hillside vineyards, it's no wonder this small town attracted the likes of Jackie Kennedy Onassis and Elizabeth Taylor, both of whom once called Middleburg home. Downtown Middleburg's walkable historic district holds an assortment of well-preserved storefronts that now accommodate one-of-a-kind boutiques such as Brick and Mortar Mercantile and Kade.
Those looking to wet their whistle can head to the historic Red Fox Inn & Tavern to savor a selection of local game and seafood at one of America's oldest inns. Locals venture to sunny Glenwood Park every year to partake in equestrian competitions such as the Middleburg Spring Races, Virginia's oldest steeplechase event. Others prefer to visit the five-star resort, Salamander Middleburg, to enjoy the many amenities, as well as annual festivities such as the Middleburg Film Festival.
Leesburg
Stroll historic downtown Leesburg, and you may feel as though you've taken a step back in time. Explore King Street, where colonial-era buildings house everything from artisanal coffee shops to art galleries. The Tally Ho Theater is a music venue notable for its old-world character, while the arts and cultural district offers numerous public murals, statues, and even a sculpture garden, all explorable with Loudoun Art Tours. Downtown Leesburg is also home to several breweries and eateries, such as the family-owned Black Hoof Brewing Company and the longstanding Lightfoot Restaurant. Formerly a People's National Bank, this historic building was transformed into a fine-dining establishment, now complete with fireplaces, chandeliers, and a piano bar.
The recently renovated Loudoun Museum features several permanent and changing exhibits that showcase the county's history, while Dodona Manor, a National Historic Landmark formerly owned by General George C. Marshall and situated on nearly 4 acres of gardens, can be toured by admirers of bucolic beauty. Those desiring even more natural splendor should visit during the spring, when downtown Leesburg is transformed with vivid displays of flowers, plants, and landscaping exhibits for the annual Leesburg Flower and Garden Festival.
Warrenton
In the heart of Virginia's Horse and Wine Country, Old Town Warrenton exudes historic character. Dating back to 1808, the old jail is now home to the Fauquier History Museum, which houses artifacts from the Civil War, the Revolutionary era, and Native American peoples. Old Town also features several boutiques, art studios, and galleries, such as Berkley Gallery and Studio 81, ideal for art lovers who wish to take a class or immerse themselves in the town's creative spirit.
Nearby, the Warrenton Horse Show Grounds host some of the longest-running equestrian events, such as the annual Warrenton Horse Show, where you can watch thoroughbreds compete in a variety of competitions. Located at the foot of the Blue Ridge Mountains, Old Town offers wide nature views at locales like Rady Park with its woodland walking trails. Those who prefer a scenic drive can take a trek to one of the many surrounding vineyards or to Shenandoah National Park, where wildlife abounds and there are trails aplenty.
Winchester
Old Town Winchester is most notable for its historic architecture and active open-air marketplace, The Loudoun Street Pedestrian Mall. Listed on the National Register of Historic Places, the area is abundant in cafes, retail shops, historic landmarks, and fun year-round events. The historic district also offers attractions such as the Shenandoah Valley Civil War Museum, located within the Frederick County courthouse. Built in 1840, this Grecian-inspired courthouse was used as a hospital, prison, and barracks during the Civil War. Today, it showcases artifacts and captivating imagery from that tumultuous period in American history.
Old Town is also where locals gather for seasonal events such as the spirited Shenandoah Apple Blossom Festival and the Winchester Winter Village. Several of the neighboring farms and orchards also offer seasonal fun such as berry picking, farmers' markets, hayrides, and haunted houses. Meanwhile, Jim Barnett Park provides scenic views and lots of outdoor recreation with walking trails, a fishing lake, an outdoor swimming pool, and multiple athletic fields and courts.
Cape Charles
Known for its proximity to the Chesapeake Bay, this small beach town features turn-of-the-century architecture and a city center bordered by pastel storefronts. Explore the shops and galleries along Mason Avenue, or enjoy waterfront dining at restaurants like Sunset Beach Bar and Grille. Visitors looking to spend a relaxing day by the water don't have to look far, with Cape Charles Beach being just a short walk from downtown. Furthermore, Tidewater Charters offers fishing expeditions so you can spend a day on the water with friends.
The nearby Eastern Shore of Virginia National Wildlife Refuge is a great place to immerse yourself in nature, with hiking trails and a butterfly garden. Moreover, the Cape Charles Museum & Welcome Center offers a variety of exhibits for those keen to learn more about the local history.
Smithfield
Affectionately known as the "Ham Capital of the World" due to its renowned centuries-old dry-curing process, Smithfield's main strip is equally well known for its abiding seaport character, with beautifully preserved 18th-century architecture, boutique shopping, and waterfront views of the Pagan River. Located along Main and Church Streets, Downtown Smithfield is bursting with history and culinary delights. Visit the Historic District and delve into the county's lore at the Isle of Wight County Museum, with exhibits showcasing Native American and colonial artifacts and Smithfield's ham industry.
As expected, Downtown Smithfield offers much more than just cured meats, with a wide array of delicious cafes and restaurants, such as Wharf Hill Brewing Company and the classic Smithfield Ice Cream Parlor, complete with 1950s decor. Smithfield Station Waterfront Inn sits beside the Pagan River and offers visitors spacious rooms, exquisite vistas, and fresh seafood at the restaurant overlooking the marina.
Main Streets, Not Plain Streets
Each of these downtown strips offers arts and entertainment while still preserving the history and nature that surround them. The Culpeper Mural Tour and the Loudoun Street Pedestrian Mall in Old Town Winchester both reward a long walk and a slow look. Whether you prefer the enduring colonial-era architecture of Leesburg, the mountain vistas around Middleburg, or the marina setting of Cape Charles, these sweet spots show a different side of Virginia at every stop.
