9 Small Towns in Virginia With the Best Downtowns

Virginia was once the birthplace of the nation, boasting Civil War battlefields and colonial landmarks that still shape places like Staunton’s Beverley Historic District. Independently owned businesses are favored in small towns like Lexington, where red-brick sidewalks, specialty shops, and landmark sites like the Stonewall Jackson House keep downtown rooted in the past. And in Abingdon, a 20-block historic district, the long-running Barter Theatre, and easy access to the Virginia Creeper Trail create a downtown that blends culture with outdoor adventure. Below are 9 cozy small towns with some of the best downtowns in the state.

Culpeper

In addition to Main Street, Davis Street is another popular downtown street in Culpeper, where you will find 19th- and 20th-century brick buildings. Nearby is the grand historic Culpeper County Courthouse and an active Amtrak depot. George Washington was once the land surveyor of that region back in 1749, while the area now functions as a modern retail and dining hub with cafes like Raven's Nest Coffee House and unique shops like Pepperberries. Visitors will also find sites like the Museum of Culpeper History and nearby Civil War battlefields. Just down the road from the main strip is the Library of Congress Packard Campus Theater, a gorgeous Art Deco building housing a massive audio-visual archive and a former Cold War bunker, known for screening free films.

Middleburg

Downtown Middleburg is located in the foothills of the Blue Ridge Mountains, with more than 160 structures listed on the National Register of Historic Places, many dating back to the late 18th to mid-19th centuries, along Washington Street. The town is known as “Nation’s Horse and Hunt Capital,” due to its prominence in fox hunting and equestrian activities, with institutions like the National Sporting Library & Museum that document equestrian sport and history. The walkable village includes locally owned boutiques such as Brick and Mortar Mercantile and historic dining at The Red Fox Inn & Tavern, one of the oldest continuously operating inns in the United States. The perfect place to end the day is at one of the nearby wineries, like Boxwood Estate Winery, where you can explore the grounds and do a bit of wine tasting.

Lexington

The charming downtown of Lexington remains remarkably intact, with a mix of Federal, Greek Revival, and Victorian-era buildings, alongside red-brick sidewalks that evoke an 1860s appearance. Landmarks like the Stonewall Jackson House, a museum showcasing many of Jackson’s personal possessions, and the historic Lee Chapel are deeply rooted in their legacies.

Main Street is compact and lined with independent specialty shops such as Cheese to You and The Bookery, a cozy bookstore packed with rare books. Seasonal events, including the annual Candlelight Processional & Community Tree Lighting, mark the start of the holiday season with a procession led by a horse-drawn carriage, while nearby destinations like Natural Bridge State Park and the Blue Ridge Parkway draw visitors beyond downtown.

Staunton

Spanning six historic districts with 18th-20th century architecture largely untouched by the American Civil War, is the remarkable village of Staunton. The Beverley Historic District is considered the heart of downtown for its walkable Main Street charm, with independent shops, limited chain stores, and Victorian buildings. Curated boutiques like Made, a general store selling handmade goods, and cafes like The By & By add to the area’s inviting character. The Queen City Mischief & Magic is an annual Harry Potter event that energizes the city center. There is also the American Shakespeare Center, housed in the Blackfriars Playhouse, the world’s only re-creation of Shakespeare’s indoor theater, which continues to draw visitors and support a thriving tourism economy.

Winchester

Downtown Winchester, affectionately known as Old Town Winchester, is centered on the Loudoun Street Walking Mall, a pedestrian-only brick corridor with retail and dining. The surrounding 45-block historic district features a mix of Georgian and Greek Revival architecture and Civil War-era sites, including notable landmarks like the George Washington's Office museum. Regular events bring constant foot traffic, such as the local farmers market held every Saturday from June to October, and the Shenandoah Apple Blossom Festival held in the spring, featuring parades, a carnival, and luncheons. Additionally, just south of downtown, you will find time-honored sites like the Patsy Cline Historic House, a non-profit organization open for guided tours.

Cape Charles

Mason Avenue is the main commercial thoroughfare in Cape Charles, within a historic district of numerous well-preserved Victorian and Colonial Revival buildings. The absence of national chains keeps the mix of commerce more independently driven, with stores like the cozy Brown Dog Ice Cream shop, which uses only local ingredients, and Cape Charles Coffee House, serving up its signature drink, “Cafe Cape Charles.” Its location on the Chesapeake Bay connects the downtown area to a public beach and harbor. The nostalgic LoveFest, held in late summer, is a 1960s-themed celebration in which locals compete for best costume and participate in tie-dying and dancing.

Smithfield

Known as the "Ham Capital of the World" for its historically significant and legally protected salt-cured ham industry, Smithfield is a charming town with much to offer. Notable landmarks, such as St. Luke’s Church & Museum, the oldest intact Gothic brick church in Virginia, feature an ancient cemetery. Independent businesses such as the Christmas Store and When Pigs Fly Magic Happens are concentrated on Main Street near the Pagan River waterfront. The Smithfield Farmers Market is also on Main Street, while nearby Windsor Castle Park offers opportunities for outdoor recreation. Nearby institutions such as the Isle of Wight County Museum document the area’s heritage, dating back from 1619 to the present.

Abingdon

The heart of Abingdon features a 20-block historic district listed on the National Register of Historic Places, with idyllic brick storefronts. It is home to 18th-century buildings, The Tavern (built in 1779), and well-preserved homes along Valley Street. As a regional arts hub, downtown you will find the Barter Theatre, the nation’s oldest professional theater, and supported by additional venues such as the William King Museum of Art. Additionally, downtown serves as the gateway to the 35-mile Virginia Creeper Trail and is just 12 miles from the Appalachian Trail, ensuring outdoor recreation is never far away.

Farmville

Founded in 1798, Farmville has a historic Main Street. At its center is Green Front Furniture, a landmark retailer operating out of multiple restored 1840s tobacco warehouses, creating one of the area’s most unique shopping experiences. The presence of Longwood University, a historic public arts institution, brings steady energy to the district with the Longwood Center for the Visual Arts. Outdoor recreation is easily accessible, with direct connections to High Bridge Trail State Park, a 31-mile route for hiking and biking that includes the nearby High Bridge.

Visiting Virginia could never be complete without exploring the small towns that shaped early America, offering a depth of history tied to the nation’s founding. From courthouse squares and preserved main streets to longstanding cultural institutions, these dynamic downtowns reflect centuries of continuity and change. On your next tour through the state, don't miss downtowns like Cape Charles, Farmville, and Staunton.