9 Prettiest Main Streetscapes In Virginia
Main Street is the soul of any town. It is where to go, especially if you want to feel the pulse of the community and have the all-important first impression. Virginia is defined by its jaw-dropping outdoor beauty, and you only need 10 minutes at the Shenandoah National Park to appreciate the state's surreal landscapes. However, studding the entire breadth of the state are small, beautiful towns with photo-worthy Main Streets. Some are known for their kitschy souvenir shops and bold, catchy murals, while others boast spectacular waterfronts and dreamy backdrops. So, which are the finest? Starting with Staunton, discover the 9 prettiest streetscapes in Virginia.
Staunton
The Shenandoah Valley town of Staunton has been a hot travel destination known for a walkable historic downtown area with awesome museums, eclectic boutiques and cafes, and outstanding restaurants serving delicious dishes, such as Mill Street Grill , an iconic eatery located in a converted 1890s flour mill. Six historic districts teem with beautifully restored buildings and Victorian-style architecture. Beverley Street, which runs through Staunton’s National Historic District, is widely regarded as one of Virginia’s finest preserved Victorian main streets.
Notable attractions along Beverley Street include The Split Banana, Co., a scoop shop doling out a rotating selection of ice cream in retro-style digs, and The Camera Heritage Museum, which is right next door, and which displays cameras from all historical periods and brands. Meanwhile, 17 E Beverley Antiques offers a diverse selection, ranging from clothing to kitschy vintage figurines and some cool, quirky finds. Be sure to check if there's a show at the American Shakespeare Center & Blackfriars Playhouse.
Abingdon
A far-flung highlands town with a popular rail-trail zipping down a mountainside, Abingdon always seems like a huge discovery. There's the claim that Abingdon has more restaurants per capita than New York City, and this means you should expect a fantastic dining scene with chef-driven restaurants. Abingdon’s Main Street is a tree-lined historic corridor featuring Federal, Greek Revival, and Victorian architecture, forming the cultural and civic heart of the town.
You can start with a delicious meal on the rooftop patio of Summers Roof and Cellar, amid awesome views and an intriguing atmosphere. The historic Barter Theatre, a legendary venue that has served as the town's cultural centrepiece since the 1930s, offers amazing plays and productions that are hallmarks of human creativity. You will want to explore bits of the scenic Virginia Creeper Trail, a well-maintained beauty suitable for both biking and walking, before enjoying a well-deserved massage at The Martha Washington Inn & Spa.
Old Town Winchester
Old Town Winchester, with its vibrant downtown, small business community, and walkable charm, is often named among the most unforgettable Main Streets in the United States, not just in Virginia. Loudoun Street Pedestrian Mall, listed on the National Register of Historic Places Travel Itinerary, is a quaint pedestrian walking mall bursting with outdoor cafes, fun & specialty retail shops to browse, historic attractions carrying echoes of a bygone era, and family-oriented activities throughout the year. George Washington A Wyndham Grand Hotel, a cozy property set in a stately building dating back to the 1920s, is loved for its historic charm and sense of old-world character, as well as its nice hot tub area.
Spend some time at the Shenandoah Valley Civil War Museum, a remarkable Civil War museum housed in the historic Frederick County Courthouse. It's often evocative to see some of the soldiers' names and the pictures they drew on the walls. After working up a healthy appetite, sit down to a nicely done sandwich at Water Street Kitchen, preferably at the outdoor patio, so you can soak in the views and people-watch.
Cape Charles
A Victorian-era planned community near the mouth of the Chesapeake Bay with stunning beaches that provide the perfect backdrop for relaxation, Cape Charles features brick storefronts, sandy beach, fresh seafood, and nationally ranked golf courses such as the immaculately maintained Bay Creek Golf Course, which features two signature championship courses designed by golf legends Arnold Palmer and Jack Nicklaus. Mason Avenue, the town's nerve centre, is notable for its seaside setting, preserved early-20th-century storefronts, and proximity to the Chesapeake Bay.
Cape Charles Museum has interesting local history exhibits and can serve as your first port of call. Afterward, Chase’s Soft Serve, located right on Mason Avenue, is the go-to spot for delicious ice cream that is truly creamy. Just a step away, Cape Charles Candy Company offers fudge, unique sodas, candy, Taffy, and truffles. Lemon Tree Gallery and Studio is located just across the street and features a gift shop, a fine art gallery, and live artist studios, all in one space.
Smithfield
Smithfield is Virginia’s Ham Capital. People travel from every corner to see the world’s oldest ham at the Isle of Wight County Museum, a neat space with informative exhibits providing a comprehensive look into Smithfield’s famous ham industry. Smithfield’s Main Street runs through a riverfront historic district with Colonial-era roots, catchy boutique storefronts, and a direct connection to the Pagan River. The Fiddlin’ Pig, just across the street from the museum, is a Main Street gem known for whipping up delicious fish and chips in an authentic British pub atmosphere. They also serve yummy pies with tender and flaky crusts.
Those with a sweet tooth aren't left out, either. Smithfield Ice Cream Parlor, a few blocks ahead, is an old-fashioned counter serving traditional ice cream and deli-style sandwiches. If you want a curated list of attractions to explore, the Smithfield & Isle of Wight Convention & Visitors Bureau has friendly and knowledgeable staff who go out of their way to enrich itineraries.
Culpeper
A picturesque town set in the Piedmont River Valley with nice, peaceful views that set the heart aglow, Culpeper is an adorable town to explore. You will find handsomely maintained Civil War battlefields, Colonial-era churches, and a fine exhibit of a Great American Main Street. Grand oak trees, including outside the Visitors Center, frame Davis Street, a Main Street designee since 1988. Thanks to historic district guidelines and grants, Culpeper has improved building facades, planted trees and flower boxes, and installed benches and historic street lamps. You will enjoy traipsing through wide sidewalks that provide elbow room for pedestrians and sampling the family-owned eateries that serve home-style dishes in cozy environments.
The Cameleer is a charming gift shop offering a variety of items, including candles, kitchenware, clothing, jewelry, accessories, and more. Steps away, The Frenchman's Corner of Culpeper is a world-class chocolatier that offers the finest treats from around the world. For a hearty breakfast along the stretch, Frost Cafe is a down-home joint that offers an old-timey feel and killer sandwiches. Away from the main drag, PlayDate: A Children's Museum offers a variety of interactive activities for toddlers and older kids, and is certainly one of the best children’s play places in the area.
Farmville
Farmville is an artsy and vibrant college town with funky boutiques, a historic hotel, and a nice rail-trail with views across the scenic Appomattox River Valley. Home to Longwood University, one of the oldest institutions of higher education in the United States (it was founded in 1839), Farmville has a thriving arts and culture scene. The charm-soaked Main Street has funky restaurants such as one19 - Tastefully Off-Center, a culinary rock star that boasts one of the largest assortments of Bourbons, Tequila, and Mezcal in the region. Service here is usually spot-on, and the background music is perfect.
At the Longwood Center for the Visual Arts, you will admire a collection that spans contemporary and Chinese art, folk art, African art, and local Virginia works, complemented by rotating temporary exhibitions. Keep in mind that High Bridge is less than five miles east of downtown Farmville on the rail trail. So, if you are looking for a perfect two-wheeled adventure from Main Street, this is a popular recommendation. History nerds have the Robert Russa Moton Museum, a historic landmark that tells the story of a 1951 student strike that helped usher in the Civil Rights era.
Leesburg
Named after the prominent Lee family, which included Confederate General Robert E. Lee, Leesburg boasts significant Civil War sites and historic homes, as well as cozy restaurants (especially on King Street) serving oysters, tacos, and a diverse array of farm-to-table fare. Federal-era buildings dot the stretch and transport the mind to America’s foundational years. Tally Ho Theater, which has a smash burger place connected to it, is a cozy Depression-era movie place with beautiful decor, and there are lots of places nearby to meet up for a drink, whether before or after a show.
If craving a bite, King Street Oyster Bar serves creative fish dishes and cocktails in a stylish space with a covered back patio. From here, stroll next door to the Very Virginia Shop, where you will find souvenirs like t-shirts, pens, key chains, magnets, cups, and best of all, peanuts. Just be warned that Virginia peanuts are hopelessly addictive. Birch Tree Books & Plants, a cozy space in the heart of downtown Leesburg, offers a rare combination of books and plants.
Blacksburg
With a bustling, pedestrian-friendly Main Street and a downtown area that offers a perfect blend of college-town energy and historic charm, Blacksburg rightfully rounds out the list of Virginia's most beautiful streetscapes. You will find restaurants serving delicious Southern fare, many of which regularly offer live music as well. Talking of music, weekly jam sessions at Market Square Park are especially popular. The Lyric Theatre, originally constructed in 1929, wows patrons with its original 1930 tapestries, not to mention the best-tasting popcorn in Southwestern Virginia.
G2’S All American Grill, steps from the theatre, serves flavourful dishes, notably chicken tenders and fish sandwiches, in a fun, casual atmosphere. You will want to check out the Blacksburg Museum and Cultural Foundation, which tells the foundational history of the area through evocative exhibits. If local history doesn't float your boat, you may want to opt for Miller Off Main St Galleries, a great place to discover talented local artists, and whose in-house photographer has an unmatched eye for framing all types of art.
So, Main Streets are not just places where you dash to catch a train or grab a quick bite during a 10-minute lunch break. Main Streets are essentially living front porches; places where history, creativity, and daily life meet. From heart-stirring Victorian architecture to colorful flower planters and Civil War-era storefronts, some of Virginia's main thoroughfares deserve a whole day of leisurely exploration.
