10 Virginia Towns With Unforgettable Main Streets
Most tourist traffic in Virginia leads to famous destinations like Virginia Beach and Richmond. Given their vibrant downtown districts and lively shopping and dining scenes, it is no surprise they are at the top of many visitor itineraries. However, the Old Dominion is too vast to confine yourself to the cities. Beyond the hustle and bustle, multiple small towns expose holidayers to the overlooked side of the state.
Some of these hidden gems harbor the true heart and soul of the state, which is reflected in their rich histories and cultures. Furthermore, they have vibrant Main Streets where the true character of the community manifests in the form of stunning architecture, notable landmarks, and eclectic local businesses. From Winchester's historic charm to Wystheville's artistic allure, these are Virginia towns with unforgettable Main Streets.
Lexington
Lexington is a historic community in Rockbridge County, whose long standing heritage is reflected in the chain of vintage structures lining its downtown district. A walk down Main Street, Lexington reveals several landmarks that offer a glimpse into the past, including the six-story Gin Hotel, which was constructed in 1926. The Jackson House Museum is another notable building not far from the major thoroughfare that transports you back to the mid-19th century. It preserves the former home of General Thomas Jackson from the Civil War and depicts his life before the conflict.
The corridor also reveals a lively farm-to-table dining scene and craft brewery culture, which visitors can sample at Heliotrope Brewery. This quaint establishment serves delicious brick-oven pizzas with freshly produced ales and lagers.
Marion
Like any other college town, Marion has an active downtown district that is always bustling with activity. Main Street is a charming mix of the town's art scene, historical heritage, restaurant landscape, and all-round entertainment. Highlights along the avenue include the Lincoln Theatre, a Mayan Revival-style theater from 1929 that connects the community to the arts through stage performances, live cinema, and education programs. Multiple eateries dot the street, serving various flavors from different cultures.
Travelers can stop by Yummy Yummy Japanese Restaurant to sample scrumptious Japanese dishes or stick to American comfort foods at Pizza Perfect On Main. When you need a nice night spot, Main Street offers the General Francis Marion Hotel, which boasts unmatched ambiance and luxurious amenities.
Warrenton
Warrenton has a rich heritage dating back to the early 1800s when it was founded. However, its downtown district perfectly merges the new with the old, as a collection of vintage structures houses modern boutiques, restaurants, and other businesses. The main avenue cuts through the heart of Old Town Warrenton and boasts multiple restaurants, inviting vacationers to enjoy tasty pizzas at Licorice Pizza. You can also take the kids for family-friendly fun at Arcade Underground, which treats them to the ultimate gaming paradise.
A short walk will bring you to the Fauquier History Museum at the Old Jail. This vital landmark offers a vivid glimpse of the formative years. It contains two historic buildings, an 1808 brick and an 1823 stone building, with curious artifacts dating back to the early 19th century.
Staunton
This Augusta County community, 42 minutes west of Charlottesville, boasts an award-winning Main Street with a dense cluster of businesses, antique stores, boutiques, and restaurants. It is one of Virginia towns with unforgettable Main Streets and hosts several performance art venues, including the American Shakespeare Center's Blackfriars Playhouse. Furthermore, visual art lovers can browse intricate pieces by local and regional artists and learn some history at the R.R. Smith Center for History and Art.
Not too far away, the Woodrow Wilson Presidential Library and Museum explores the life and times of the United States' 28th president while preserving and interpreting his rich legacy to visitors. Finally, those who fancy a casual shopping experience can sample local produce at the Staunton Farmers' Market.
Winchester
Winchester's charm is embedded in its Old Town district, where antique architecture and historic treasures accord visitors a remarkable sightseeing experience at every turn. Main Street forms the heart of Old Town Winchester, dotted with notable landmarks, sites, and local businesses. Highlights include the Shenandoah Valley Civil War Museum, which exhibits rare Civil War artifacts and archives in an authentic 19th-century courthouse. The Bright Box Theater stages dozens of exciting theater shows in an upbeat atmosphere throughout the year.
Shoppers will relish sorting through an assortment of merchandise at the Loudon Street Pedestrian Mall. Meanwhile, those visiting with family can have classic fun at Worlds Away Escape. This remarkable facility features interactive challenges requiring critical thinking and problem-solving skills.
Berryville
This unassuming little town in Clarke County has a pedestrian-friendly downtown area that offers a glimpse of the yesteryears with its historic architecture while embracing modern trends with chic boutiques and restaurants. The main thoroughfare is home to the Clarke County Historical Association Museum, whose library of exhibits chronicles the community's past and that of surrounding regions. It is also a nice spot for casual shoppers to explore, offering a chance to sort through a curated collection of gifts, jewelry, accessories, and other cute items at Modern Mercantile.
The same is true for Berryville treasures, where you can find unique souvenirs produced by local crafters and artisans. When tired from all the walking, there is a cool, grassy nature spot at Rose Hill Park where you can relax and catch your breath during an easygoing picnic.
Leesburg
Leesburg impressively merges the new with the old in a vibrant historic district boasting a display of Greek Revival, Georgian, and Classical architecture on vintage structures listed on the NRHP. Strolling through the main streets feels like a trip down memory lane, thanks to preserved treasures like George C. Marshall's Dodona Manor, a National Historic Landmark dating back to the 19th century. The Tally Ho Theater is an excellent example of how the present interacts with the past. This popular event venue in the heart of the historic district stages live music concerts and theatrical productions featuring touring acts and homegrown talent.
Guests also have a chance to unwind with a pint of beer at Spanky's Shenanigans while listening to live music. Alternatively, Ida Lee provides a quiet outdoor space for an array of nonchalant recreation activities, from water slides and a lazy river to an obstacle course.
Williamsburg
Williamsburg is a living history museum that captures the early years of colonialism in Virginia. It maintains a vast collection of sites and markers offering a vivid glimpse of life at the time and takes visitors on a riveting journey through time. Walking down Duke of Gloucester Street, you will notice the lovely mix of colonial-era structures housing pubs, coffee shops, galleries, and other businesses. The Cheese Shop is a beautiful spot to enjoy a delicious sandwich and beverage in a romantic atmosphere. You can also pause to admire the rustic yet intricate architecture of the Bruton Parish Episcopal Church, established in 1674.
The church is a walking distance from the Art Museums of Colonial Williamsburg, which harbors a complex of galleries showcasing colonial and modern folk art. It boasts thousands of exhibits created by amateur and seasoned craftsmen, ranging from fine and mechanical to decorative pieces.
Middleburg
Middleburg was nicknamed "Nation's Horse and Hunt Capital" to allude to its rich equestrian and sports-hunting heritage. For years, it has drawn visitors from across the country with its steeplechase and foxhunting events. This historic community has a busy main street that serves as the entertainment and commerce epicenter, hosting attractions like the Red Fox Inn & Tavern. The historic establishment dates back to 1728 and offers guests rustic accommodation. Meanwhile, Mt. Defiance Cidery and Distillery welcome newcomers to sample Middleburg's artisanal spirits and cocktails.
Mains Street Middleburg is also home to the Middleburg Community Center, an important gathering spot for the townspeople, which runs educational, cultural, and social programs to enrich the people's lives. When you need something to eat, consider trying delicious American fare with a traditional twist at Harrimans Grill.
Wytheville
Wytheville's beautiful downtown area showcases an impressive blend of the arts, history, and entertainment, culminating in a vibrant atmosphere that is always teeming with tourists and locals alike. Its main street is lined with major points of interest, and history lovers will fancy touring the Edith Bolling Wilson Birthplace Museum to explore the rich legacy of the former first lady. Also, the Millwald Theatre is the local cultural hub, providing a 500-seater auditorium with state-of-the-art acoustics where townsfolk gather to watch the latest movies and exciting theatrical performances.
At Seven Sisters Brewery, tourists have an opportunity to taste locally crafted beer from southwest Virginia, while Jo Jo's Attic invites souvenir lovers to sort through an assortment of vintage treasures, including home decor items, crafts, furniture, antiques, jewelry, and other primitives.
Final Thought
Each of these Virginia towns with unforgettable Main Streets demonstrates distinct charm and character that alludes to the rich diversity of the Old Dominion. Their peaceful and walkable downtown districts allow visitors to explore the different offerings at a comfortable pace while learning something about local culture. Whether delving into the enduring history of Winchester or enjoying a retail therapy session in Warrenton, each destination is as fulfilling as the next or the one before.
