9 Picture-Perfect Main Streets In Virginia
As one of the original 13 colonies of the United States, historic Virginia is a beautiful place to visit. Travel back in time with a stroll down historic downtown areas and gaze upon uniquely charming architecture from decades past. There are numerous things to do in Virginia, from museums to delectable restaurants. Virginia is a place with diverse small towns where you can truly relax and take your time exploring.
Out of Virginia’s many small towns, these nine offer some of the most picture-perfect main streets. Each town is full of fun things to do in and around the heart of the city, so there is no need to travel far once you get to your destination.
Fredericksburg
The well-preserved historic town of Fredericksburg is located in northeastern Virginia, in Spotsylvania County. Originally settled in 1671, Fredericksburg showcases its history in its old buildings, many of which date back to the 18th and 19th centuries, located in the downtown area. Fredericksburg offers an array of historical sites to visit, natural beauty, and delicious food.
On Charles Street, visitors can find one of the town’s most notable historic landmarks, the Mary Washington House. In 1772, George Washington purchased the house for his mother, Mary Ball Washington, who lived in it for 17 years. The white frame house is within walking distance of another must-see historical site, the Kenmore, on Washington Avenue. The stunning 1770s Georgian-style brick mansion was home to George Washington’s sister, Betty Washington Lewis, and her husband and features 18th-century artifacts throughout the rooms.
Right in the downtown area, on Sophia Street, lies Riverfront Park, a 4-acre property offering picturesque views of the Rappahannock River. The open space hosts events throughout the year, and in the hillside area between the Rappahannock River and the park’s promenade, you can find a meadow. An assortment of plants, like Mountain Mint and Virginia Wild Rye, can be seen here. In downtown Fredericksburg, you have your pick when it comes to delectable dining. The Colonial Tavern, located in the former depot of the Virginia Central Railway, serves a mix of Irish and American cuisine.
Staunton
Staunton, Virginia, settled in 1736, is known for its well-preserved architecture throughout the town. The deeply historic city lies along the Shenandoah River in north-central Virginia, between George Washington National Forest and Shenandoah National Park. Staunton's downtown is home to unique historical buildings and a Shakespearean playhouse. Some of Staunton's oldest buildings are dedicated museums, while others blend history with modern amenities. One such place is the Blackburn Inn. The 1828 property functions as a boutique inn and conference center, but visitors can also take guided tours to view the behind-the-scenes of the facilities and learn about how the property was once a 19th-century mental health facility.
When creating an itinerary for Staunton, be sure to add the Woodrow Wilson Presidential Library and Museum to your list. The house is the very home where the former U.S. president was born. It features exhibits such as a World War I trench exhibit to aid guests on their journey through time. Afterward, enjoy local entertainment at the BlackFriar Playhouse on Market Street, an American Shakespeare Center. Open year-round, the playhouse puts on performances of Shakespeare's plays and contemporary works.
Cape Charles
The friendly small town of Cape Charles welcomes visitors with views of Victorian-era buildings and quaint storefronts. It sits at the mouth of the Chesapeake Bay on the state’s eastern shore and is home to a beautiful beach, rustic fine dining, and loads of history. In the downtown historic district, visitors can find the Cape Charles Beachfront. The free public beach boasts waveless shallow waters of the Chesapeake Bay, making it the perfect place to relax and safe for families with small children. Pursue additional seaside fun with a meal at The Shanty. The seafood restaurant, situated on Marina Road overlooking the Chesapeake Bay, serves fresh oysters, lobster rolls, and fried baskets alongside waterfront views.
Much like many of Virginia’s towns, Cape Charles is full of historical buildings. Take a stroll throughout the town’s neighborhoods, and you will be sure to find beautiful historic homes lining the streets. Past the town’s water tower is an impressive red brick building housing the Cape Charles Museum and Welcome Center. Owned by the Cape Charles Historical Society, the museum showcases the town’s heritage from the 1880s through the mid-20th century, including an exhibit on a 35-million-year-old crater found beneath the Chesapeake Bay.
Bristol
Bristol is a fun place to visit and live. The city rests in an extension of the Shenandoah Valley on the border between Virginia and Tennessee. Bristol’s historic Main Street, named State Street, is a unique location because the state line between Virginia and Tennessee runs right through the middle of State Street, making it entirely possible to put one foot in Virginia and one foot in Tennessee at the same time. Bristol offers a lot of charm and entertainment in the form of historical sites and local arts.
The Bristol Train Station is one of the main reasons the town was founded. Built in 1902, the train station boasts a timeless design, featuring cathedral ceilings, chandeliers, and Gothic-style architecture in the waiting room, known as Kegley Hall. The train station is worth checking out simply to see a piece of Bristol’s heritage. One can also enjoy local performances at the Paramount Center for the Arts. The 1930s center presents dance, comedy acts, films, theater, music, and family-friendly entertainment in an Art Deco setting. Also in the downtown area is the Country Music Mural, which depicts early country artists such as Jimmie Rodgers and The Stoneman Family.
Farmville
Centrally located in Virginia is Farmville, a small town established in 1798 with a welcoming atmosphere, loads of history, and outdoor appeal. Farmville sits 65 miles west of Richmond, Virginia, offering a quaint retreat from the big city. Farmville’s downtown features quintessential old historic buildings with charming brick facades, and going right through this area is the High Bridge Trail. Over 2,400 feet long, rising 125 feet above the Appomattox River, the High Bridge welcomes hikers and bikers to explore the 31-mile trail. Erected in 1853, the High Bridge is one of Virginia’s most famous historical landmarks.
Engage with more of Farmville’s heritage at the Longwood Center for the Visual Arts. Owned by Longwood University, the museum contains over 100,000 works of art and design, spanning from ancient times to contemporary art, as well as folk art and works by Virginia artists. Dine where the locals go for breakfast and lunch at Uptown Coffee Cake. This establishment on Main Street offers locally roasted coffee, salads, sandwiches, pastries, and live music to its patrons.
Winchester
Offering an array of opportunities to transport you straight into the past, Winchester is a small town with a lot of heart and historic charm. Winchester is in northern Virginia, at the northern end of the Shenandoah Valley, northwest of Washington, D.C. The small town was settled in 1732 and named after Winchester, England, in 1752. Winchester is home to the springtime Shenandoah Apple Blossom Festival and Shenandoah University.
Old Town Winchester, a marketplace with over 250 years of history, is located in the center of the 45-block National Register Historic District. It is a quaint pedestrian walking mall equipped with outdoor cafes, retail spots, and historic attractions. Tourists and residents of Winchester can enjoy local favorites like 50/50 Taphouse, a beer hall offering 50 different beers and 50 different burgers. Nearby, the Museum of the Shenandoah Valley is a must-see attraction, located on land claimed initially by Winchester's founder, James Wood. The museum includes seven-acre gardens bursting with roses, perennial blooms, various vegetables, and four gallery spaces highlighting different works. Another notable historical attraction is the Abram's Delight Museum. Built in 1754, the house is the town's oldest home and served as the area's first Quaker meeting house. Guests can find a mix of period art and antiques throughout the museum.
Lexington
Part of Rockbridge County, Lexington lies in the west-central portion of the state, on the Maury River. History fanatics will love the Lee Chapel and Museum. Located on West Washington Street, the chapel sits on the grounds of Washington and Lee University. Completed in 1868, the building, constructed of brick and native limestone, features a Victorian-era design. Nearby on East Washington Street, you can tour the Stonewall Jackson House. Previously owned by the Confederate General Thomas “Stonewall” Jackson, the house has been a museum since 1954, featuring period-appropriate historic pieces and some of Jackson’s personal belongings.
Enjoy a craft beer on tap and a fresh wafflewich at Brew Ridge Taps on East Nelson Street in the downtown area of Lexington. The tap house and restaurant offer the largest selection of craft beer in Rockbridge County, along with a menu of tasty options, including sandwiches with waffles in place of bread. Just under 15 miles southwest of Brew Ridge Taps, people looking for an outdoor adventure can find the Natural Bridge State Park. The Virginia Historical Landmark is a 215-foot-tall natural bridge, a limestone gorge carved out by Cedar Creek. Surrounding the bridge are lush forests, rolling meadows, and ten miles of hiking trails.
Charlottesville
No matter the season, there is always something fun to do in Charlottesville, Virginia. Nestled in central Virginia in Albemarle County, Charlottesville rests at the foothills of the Blue Ridge Mountains. The small town lies on the Rivanna River, approximately 70 miles northwest of Richmond, Virginia. Planning a trip to Charlottesville is not complete without checking out the Historic Downtown Mall. Over 120 shops and restaurants housed inside historic buildings dotting Main Street make up this charming outdoor mall. Here you can enjoy entertainment such as live music at the Jefferson Theater. Constructed in 1912, the theater originally showcased silent movies and vaudeville acts; however, it now hosts different music genres, including bluegrass, rock, country, hip-hop, and reggae.
Take the little ones for a ride on the Downtown Express, an electric trackless train. The free train rides provide a fun way for children to experience the mall with their families. Learn more about Charlottesville’s history through the Albemarle Charlottesville Historical Society. Open from Monday through Friday, free of charge, the historical group features changing, vibrant exhibits that preserve and reveal the history of Central Virginia.
Williamsburg
Williamsburg is a historic city known for its well-preserved buildings and vibrant, walkable downtown. It was settled in 1632 on the southeast side of the state on a tidewater peninsula positioned between the York and James rivers. Tourists can discover Colonial-era architecture in Williamsburg, which is an attractive option for history buffs.
Explore Colonial Williamsburg by touring historical sites like the Governor’s Palace and Gardens. The palace has been home to seven royal governors, serving as a reflection of the colony’s power and wealth. Its grounds include a remarkable maze and manicured gardens with 18th-century features, such as the canal and ice mount. Close by, you can tour the George Wythe House, the original home of one of the signers of the Declaration of Independence. Inside the home, you can see rooms depicted in period-appropriate style.
Williamsburg’s downtown presents an array of shopping and dining options, such as The Peanut Shop. Browse delectable Virginia peanuts, chocolates, seasoned nuts, and snack mixes to take back home or snack on throughout your vacation. Grab a bite at the Blue Talon Bistro for a taste of French Bistro tradition and American fare. Options like the classic Steak Frites and truffle fries are crowd pleasers among locals.
Main Street Charm In Virginia
People say Virginia is for lovers, but it could also be noted that Virginia is especially for history lovers. These nine small towns in Virginia are rich in history, with their various historic sites, including Colonial Williamsburg, the over 250-year-old marketplace in Old Town Winchester, the 1828 Blackburn Inn in Staunton, and the Mary Washington House in Fredericksburg. The state also flaunts endless natural beauty, offering a picture-perfect beach in Cape Charles and a High Bridge in Farmville. The food scene throughout Virginia’s small towns is incredible, with restaurants like Brew Ridge Taps in Lexington. You cannot go wrong with choosing one of Virginia’s small towns for your next adventure.
