The Best Small Towns in Virginia for a Weekend Retreat

Blending beautiful natural landscapes, captivating colonial history, and unique cultural heritage with trademark Southern hospitality, Virginia's charm resonates with travelers on an East Coast itinerary. Amidst the state's diverse geography and backdrop lie picturesque small towns harboring the heart and soul of the Old Dominion. From beautiful villages on the Blue Ridge Mountains and relaxed communities on the banks of the Shenandoah River to tranquil towns along the Atlantic coastline, these quintessential Virginian hamlets are perfect for a restorative weekend escape from city life.

Their slow pace of life and richly rural atmosphere invite city dwellers to escape the rigors of urban life and embrace the perks of small-town living during a rejuvenating weekend escape. Whether you want to stroll through historic Main Streets, explore unique traditions, sample delicious local cuisine, or immerse in the great outdoors, these delightful towns in Virginia are worth consideration.

Cape Charles

A wonderful escape to Virginia's cozy Eastern Shore awaits in this tiny Northampton County village. Home to about 1,200 residents, Cape Charles welcomes tourists to relax and unwind in its secluded open spaces. The Cape Charles Natural Area Preserve is tailored for meditation, presenting a serene setting with a lengthy boardwalk traversing a wooded section into the open coast. The town also oozes rustic charm with its impressive cluster of over 500 historical structures hinting at its storied legacy.

Walking through the downtown area reveals a bustling art scene featuring a couple of quaint art galleries. You can stop by the Ellen Moore Gallery to browse a variety of fine art pieces by local, regional, and international artists. Meanwhile, the town has a buzzing bar and restaurant culture that caters to all taste buds. When peckish, remember to pop into The Shanty for scrumptious seafood, with options like fried oysters, tuna, and shrimp on the menu. And for your nightly stays, Hotel Cape Charles provides cozy accommodation in the town.

Williamsburg

Step back into the bygone eras in a living history museum in this city bordering James City County. Teeming with historical sites, Williamsburg is a rich tapestry of state and national history, offering an immersive journey into the American Revolution era. Tourists can start their itinerary at the Colonial Williamsburg Visitor Center to discover life as it was in 18th-century America. The site features a mix of historical landmarks and experiences taking visitors back to Colonial Virginia. The Peyton Randolph House is arguably the most interesting site in the historic district. Dating back to around 1715, it is one of the oldest structures in the museum and among America's most haunted buildings.

But there is more to Williamsburg than its unparalleled history. At Busch Gardens Williamsburg, families are invited for ageless, unadulterated fun featuring roller coaster rides, live shows, kid games, and other fun activities on a 422-acre amusement park. Finally, tourists can spend the night at Comfort Suites Williamsburg Historic Area to be close to all the action.

Charlottesville

Home to the University of Virginia, Charlottesville is a bustling college town teeming with attractions, from cultural and historical to natural. It presents the ultimate gateway to Shenandoah National Park, which harbors endless recreation opportunities across its 200,000-acre expanse, including hiking, mountaineering, hunting, camping, and fishing. Thanks to the University of Virginia, Charlottesville has become a regional arts and culture hub, hosting an impressive selection of art centers. Guests and locals alike constantly gather inside The Paramount Theater to catch an array of stage performances at this rustic venue.

Several historical landmarks in the town bear witness to Charlottesville's colorful past, none more prominent than Monticello. This historic home and plantation housed America's third president and author of the Declaration of Independence, Thomas Jefferson, between 1743 and 1826. There is no shortage of accommodation options in the town, from Hilton Garden Inn to Hampton Inn.

Middleburg

Despite a modest population of less than 1,000 people, Middleburg attracts travelers with its renowned fox hunting and steeplechases. It boasts a charming historic district listed on the National Register of Historic Places and harbors antique treasures like The Red Fox Inn and Tavern. Established in 1728, this rustic inn not only offers guests a cozy space to spend the night but also a rare look into the bygone eras and an intimate dining experience. Middleburg hosts the National Sporting Library & Museum, which preserves the culture of field and equestrian sports through a sheer collection of books, some dating back to the 16th century.

A bustling winery and brewery scene in Middleburg welcomes visitors to sample some of the region's best crafts at establishments like Greenhill Vineyards. One of the oldest wineries in the county, this lovely site impresses with its rustic elegance and remarkable wine-tasting opportunities.

Staunton

Famously renowned for being the birthplace of President Woodrow Wilson, Staunton allows travelers to explore the rich legacy of America's 28th president at the Woodrow Wilson Presidential Library & Museum. Apart from witnessing his birthplace, guests can browse several artifacts associated with the former president, including his typed and handwritten letters. Staunton hosts a vibrant arts community, with the popular American Shakespeare Center's Blackfriars Playhouse treating audiences to a slew of captivating stage performances.

Recreational opportunities are readily available at Gypsy Hill Park when in Staunton. Stretching more than 200 acres, it offers diverse facilities for the public's amusement, including picnic tables, a pool, a mini train, and multiple sports facilities. Meanwhile, those looking for a place to lay their head can check into the Blackburn Inn and Conference Center.

Bristol

Steeped in musical heritage, this tiny twin city straddles the Virginia-Tennessee border. It played a vital role in the growth of the country music scene, a legacy that is well documented at the Birthplace of Country Music Museum in the form of stories, recordings, exhibits, and other memorabilia. Bristol provides a wealth of opportunities for the outdoor inclined, with multiple parks dotting its territory. These include the sprawling Sugar Hollow Park, which covers 400 acres and features different amenities, such as 100 picnic sites, 75 campsites, and multiple soccer and softball fields, among others.

Visitors can also take advantage of awesome golfing sessions at the beautiful setting of Clear Creek Golf Club or try indoor golf at The Traveling Bear Indoor Mini Golf. After a tedious day of non-stop exploration, the Bristol Hotel blends convenience with luxury for remarkable accommodation in the heart of the town.

Abingdon

Small-town charm naturally blends with Southern hospitality to make Abingdon one of the most welcoming towns in Virginia. A quick weekend escape to this hidden gem in Washington County promises tourists a once-in-a-lifetime experience. The town's hospitable reputation shines through the Abingdon Farmers Market, an excellent venue to mingle with the townsfolk while shopping for local produce and wares. Elsewhere, Barter Theatre offers an opportunity to join the locals for an immersive cultural experience, comprising a variety of performances staged inside the country's longest-tenured professional theater.

For some bit of Abingon's background, you can locate the Historical Society of Washington County downtown and scope out a sheer collection of artifacts, old photos, and archives chronicling its rich past. If you need a place to rest for the night, you will find a cozy place to sleep at the Hampton Inn.

Lexington

Lexington presents a nostalgic charm that seeps through the red brick architecture decorating its historic downtown corridor. The town harbors a fair share of historical markers that indulge visitors in a quiet journey back to the eras gone by. The Jackson House Museum is a great example, representing the former residence of Confederate General Thomas Jackson. It was constructed in the mid-1800s and still maintains a number of period artifacts. Lexington is home to the Virginia Military Institute, which houses the VMI Museum. Inside, A collection of over 15,000 military-related artifacts promises to interest visitors.

Stepping outside, adventurers can explore Lexington's historic district on a laidback, narrated tour courtesy of the Lexington Carriage Company. The neighborhood also offers plenty of accommodation options strategically positioned in the middle of the town, including the Hampton Inn Lexington.

Chincoteague

Weekend escapes in Virginia do not get more soothing and relaxing than Chincoteague. This dreamy island destination on the state's Eastern Shore promises idyllic open spaces that allow you to get away from the crowds for some alone time. The Chincoteague National Wildlife Refuge is perfectly suited for this, offering 14,000 acres of secluded coastal wilderness with a mix of natural habitats. The area is more famous for the herds of wild horses often spotted grazing along the coast. Chincoteague also offers an opportunity to get into the open sea and discover the town from the water, and guests can rent a vessel from Chincoteague Island Outfitters to do this.

Away from the water, touring the Museum of Chincoteague Island provides an interesting glimpse into the region's history and culture. Its impressive collection of artifacts chronicles the various aspects of the communities that have inhabited the town, including oystering and seafood culture. When you need a spot to accommodate you for the night, try booking a room at the Chincoteague Inn.

The Old Dominion truly has no shortage of picture-perfect getaways offering a deserved break from everyday life. The diverse selection of communities highlighted uniquely takes on the charm and hospitality synonymous with Virginia. Whether seeking colonial ambiance, scenic natural beauty, or coastal tranquility, these easygoing towns in Virginia guarantee a restorative weekend experience. From leisurely strolls along historic main streets and riverfronts to outdoor recreation in the neighboring scenery, visitors are sure to leave feeling well-rested and fully re-energized.