9 Picturesque Towns in Virginia for a Weekend Retreat in 2024
Virginia, known for its rolling hills, natural beauty and historic landmarks, is home to some of the most picturesque towns in the country. From the lush landscapes of the Shenandoah Valley to the waterfront towns of Chesapeake Bay, these towns are steeped in post-card-like views and make excellent options for a weekend getaway. Travel to one of these quaint small towns from nearby cities like Washington D.C. or Baltimore to find a quiet escape full of beauty and charm.
Lexington
Tucked away in the Shenandoah Valley, Lexington is a small town with big charm. Known for its historic landmarks, including Washington and Lee University and the Virginia Military Institute, Lexington combines the feel of a college town with stunning mountain views. Nature lovers will enjoy hiking along the nearby Appalachian Trail, or strolling the Buena Vista River Walk. The region is particularly popular for spotting the vibrant colors of fall foliage, but is equally beautiful all year round.
History enthusiasts can explore the Stonewall Jackson House. This historical building was the home of Confederate general Thomas "Stonewall" Jackson from 1858 to 1861. Don’t miss the 200 year old Georges Inn which offers 33 unique guest rooms in upscale accommodations across three 200 year old historical buildings. Its location right in the center of town makes it an ideal choice for those visiting for a short stay.
Staunton
Another small town with lots of historic charm is Staunton. It is located in the Shenandoah Valley, and is a vibrant town known for its well-preserved historic architecture and thriving arts scene. Visit the Blackfriar’s Playhouse for live performances of Shakespeare’s plays, or browse the galleries at R.R. Smith Center for History and Art.
The town’s beauty really shines in the surrounding landscape. Nature lovers can explore the nearby Blue Ridge Parkway, The parkway is the longest linear park in the US and runs for some 470 miles through Virginia and North Carolina. Visitors can take a relaxing drive along the parkway, taking in gorgeous vistas, mountains, and the Appalachian Highlands. Another great option for viewing the scenery is biking. Staunton has a variety of bike paths in and around the valley and Montgomery Hall Park including paved paths, gravel roads, and mountain biking trails. Ambitious bikers or hikers can also enjoy stunning views at Betsy Bell Wilderness Park. The park includes a nearly 2,000 foot observation tower with views of the Shenandoah Valley and Blue Ridge Mountains.
Make the most of the picturesque landscape by camping in one of the local campsites like Walnut Hills Campground. For something a bit more luxurious, try the 1900s mansion The Historic Berkeley Place, the castle-like Historic Inn at Oakdene, or Montclair Bed and Breakfast.
Luray
Another picturesque small town in the Shenandoah Valley is the town of Luray. It is most famous for the Luray Caverns, a breathtaking underground wonder that is the largest cavern in the eastern United States. The charming town also offers scenic views of the nearby Shenandoah National Park, where hiking, camping, and wildlife viewing opportunities abound. For water sports and boating, visit Lake Arrowhead at the base of the Blueridge Mountains.
Luray also has a lot of charm in its downtown. For a tranquil stay, The Mimslyn Inn offers comfortable accommodations with beautiful mountain views. Whether you’re exploring the caverns or enjoying the natural beauty of the surrounding countryside, Luray makes for an unforgettable weekend retreat.
Middleburg
In the heart of Virginia’s wine and horse country, Middleburg offers a charming countryside escape. Known for its lush vineyards and equestrian culture, this historic town is a dream destination for wine lovers and outdoor enthusiasts. Visitors can tour local wineries such as Boxwood Estate Winery. Boxwood Winery has links to Revolutionary, Civil War American history, and is also an award-winning horse farm. The property occupies 26.5 acres of the historic landmark farmland and vineyards.
Many of the buildings in the area are former historical landmarks, and there are over 160 buildings in town that are listed on the National Register of Historic Places. Check out the Aldie Gristmill, built between 1807 and 1809, and witness a demonstration of live mill grinding. Other historical buildings include the Red Fox Inn & tavern, built in 1728. This historic fieldstone inn was once a staple of hunting culture in the area, but has since been converted into a gorgeous stately inn and popular wedding venue. Also on the hunting vibe is the National Sporting Library & Museum. Founded in 1954, the museum hosts exhibits and art pieces dedicated to telling the region's rich hunting history, including angling, horsemanship, shooting, foxhunting and more.
Like much of Virginia, all of the town’s gorgeous architecture and history is overlooked by the majesty of Blue Ridge and Bull Run Mountains. Visitors can take in the scenery from town, or venture into the wilderness for hiking, biking, fishing and boating opportunities.
Cape Charles
Bay Creek in Cape Charles, VA.
Cape Charles is a small beach town located on Virginia’s Eastern Shore. It offers a slower pace of life with a charming coastal vibe. Its sandy shores, pastel-colored homes, and inviting marinas make it perfect for a relaxing waterfront getaway. Visitors can kayak along the Chesapeake Bay or explore Kiptopeke State Park for hiking and birdwatching.
History enthusiasts can also take advantage of the various historical buildings in town like Cape Charles Memorial Library, or the Historic Palace Theatre. For accommodation, The Hotel Cape Charles, a boutique property, offers modern accommodations just steps from the beach or try one of the various B&Bs like Fig Street Inn. With its relaxed atmosphere and stunning sunsets, Cape Charles is the perfect spot for a peaceful seaside retreat.
Chincoteague
Chincoteague National Wildlife Refuge Showing Wild Horse Eating Grass, Virginia.
Like Cape Charles, the town of Chincoteague is another gorgeous Virgina beach town. The area is best known for its wild ponies and pristine beaches, and is a wildlife lover’s paradise. The town sits on Virginia’s Eastern Shore, adjacent to the Chincoteague National Wildlife Refuge. The Refuge offers opportunities for hiking, birdwatching, and of course, viewing the famous wild ponies. Take in the stunning coastal views and white sand beaches, and enjoy birdwatching, hiking, and kayaking along Assateague Island. Don’t miss the Assateague Lighthouse, a scenic landmark along the coast.
In town, stop in to one of the local restaurants like Don’s Seafood Restraunt or Bills Prime Seafood and Steak to taste some of the fresh-caught local seafare the region is so famous for. For accommodation, The Chincoteague Island Boutique Hotel offers cozy waterfront accommodations with easy access to the beach and town. With its mix of natural beauty and seaside charm, Chincoteague is a perfect retreat for those looking to escape into nature.
Irvington
The coastline of the Rappahannock River.
Irvington is yet another charming town in the Chesapeake Bay area. Tucked in the Northern Neck region along the Rappahannock River, Irvington is a quiet yet sophisticated town known for its waterfront views and refined charm. It is a great place for a weekend retreat, being close to Washington D.C., Northern Virginia, Baltimore, Richmond, and Hampton Roads. Visitors can tour the Steamboat Era Museum to learn more about the town’s history.
The scenery is one of the biggest draws in the area. Stroll the harbor, venture out on the bay, or take advantage of some of the delicious local fare. Irvington has an award-winning Farmers Market that serves up a range of fresh fish, local Rappahannock River oysters, and the delicious Chesapeake Bay blue crabs. Visitors can also check out the microvineyard The Dog and Oyster Vineyard, which is tucked inside the Hope and Glory Inn. Other options for accomodation in town include the luxurious Tides Inn which offers beautiful waterfront views and a full-service spa, or the impressive Tides Inn that sits on the peninsula. Tides Inn has one of the most beautiufl views of Carter's Creek and Chesapeake Bay, making it an ideal place for those looking for a picturesque weekend retreat.
Smithfield
St Lukes Church and Cemetery in Smithfield Virginia.
Like Irvington, Smithfield, Virginia is a charming riverside town known for its historic homes and Southern hospitality. The town dates back to 1752, and has a number of historic buildings and sites. Take a historical walking tour through town to hit all the local stops. Don’t miss the Isle of Wight County Museum, Schoolhouse Museum, and the Nelms House. Explore the beautiful Windsor Castle Park, a riverside park complete with over 4 miles of trails like the Virginia Birding and Wildlife Trail. There are also picnic areas, and a kayak and canoe launch area for those who want to venture out onto the water. The park also includes the Windsor Castle Historic Site.
Don't miss the Historic Fort Huger which sits about 8 miles from downtown Smithfield. The fort was once a strategic Civil War fort, and it overlooks the scenic James River. Visitors can take a self-guided tour and see attractions such as the ghost fleet, mounted cannons, and informational plaques. Smithfield is also home to various farms and vineyards where visitors can enjoy local food and wine among pictueresque scenery. See the beautiful lavender fields at Dream Weavers Farm, shop for produce or pick from a pumpkin path at Goerger Farms Produce and Pumpkins, or try some local wine at SummerWind Vineyard and Tasting Room.
Abingdon
Wooden bridge in autumn forest, The Virginia Creeper National Recreation Trail, Abingdon, VA.
Steeped in history and surrounded by natural beauty, Abingdon is one of the oldest towns in Virginia. Walk the town’s Main Street and explore the 20-block historic district. Notable buildings include The Tavern, The Martha Washington Inn, and the Barter Theatre, the longest-running professional theater in the country. Abingdon is also known for its natural beauty. One of the town’s biggest draws is the scenic Virginia Creeper Trail, a 34-mile bike trail offering breathtaking views of the Appalachian Mountains. Also check out South Holston Lake for paddling, swimming and boating, or the Hidden Valley cliffs, popular with rock climbers. Abingdon’s rich arts scene and its proximity to outdoor adventures make it a perfect blend of culture and nature for a weekend escape.
Virginia’s picturesque towns each offer something unique for a weekend retreat in 2024. From the scenic valleys of Lexington and Staunton to the coastal charm of Cape Charles and Chincoteague, there is no shortage of beautiful spots to relax and recharge. Whether you're seeking history, outdoor adventure, or a quiet place to enjoy fine wine and food, these nine towns promise memorable getaways. So, plan your trip and discover the perfect retreat in the charming small towns of Virginia, where relaxation, history, and nature await.
