13 Weekend Getaways in Virginia for Every Type of Traveler

Middleburg

Northern Virginia is known for its horse farms and vineyards, and there is perhaps no place more charming to experience them both than Middleburg. Explore the town's main street, and pop into shops like Crème de la Crème, where you can find hand-selected French and Italian home goods, and Highcliffe Clothier, which sells custom and tailored clothing that works equally as well in Virginia or the English countryside. Grab artisan pizza and chocolate chip-and-Virginia peanut cookies at Knead Wine before exploring the National Sporting Library & Museum's collection of equine paintings and sculptures.

Sample the area’s viticulture at wineries like Boxwood and Greenhill Vineyards, or stop for a taste of the local cider at Mt. Defiance. Middleburg’s hotels are reason enough to visit, and gems like the Salamander, Goodstone Inn, and the Red Fox Inn, a favorite of Jackie Kennedy Onassis, will make you want to extend your stay.

Richmond

Richmond is many things at once: a modern state capital, a college town, and a history-rich city. The best part about Richmond is that it embraces its multifaceted persona and provides a kaleidoscope of choose-your-own adventures for visitors. Start at the Virginia Museum of Fine Arts before continuing your exhibition adventure at The Poe Museum, which offers a fascinating look into the life and death of Edgar Allan Poe.

After a tour of the city’s rich collection of museums, head outside to Lewis Ginter Botanical Garden, a 50-plus-acre site with a butterfly-filled conservatory, children’s garden, and Victorian restoration garden. Richmond’s hip, art-filled hotel, the Quirk, is a welcome place to lay your head after a day of exploring.

Sperryville

While many people arrive in Sperryville on their way in or out of Shenandoah National Park and Skyline Drive, the tiny, blink-and-you-miss-it town packs a punch for those who choose to stay. Sperryville is a jumping-off point for several fantastic hikes, like the Hazel River Trailhead, which offers a challenging 12.7-mile out-and-back trail, and the 7.5-mile Little Devils Stairs Loop, which rewards climbers with several waterfalls and sweeping vistas. Right off one of Sperryville’s main streets, Sperryville Pike, the Rappahannock Walking Trail offers a stroll rather than a sweat.

After your hike, relax at Pen Druid Fermentation, which makes native beers and natural ciders, or Copper Fox Distillery, which concocts bourbons, brandies, and ryes. Stop into Sperryville’s compact Corner Store for local produce, fresh bread, pies, and quiches, plus an expertly curated selection of wines from Virginia and beyond. Further up the road, you’ll find galleries, potters, and a great place to refuel with a cup of coffee: Before & After. Don’t leave without trying the pizza at Rappahannock Pizza Kitchen, a cocktail at Francis, or an intimate, candlelit dinner at the renowned 20-seat restaurant The Blacksmiths. The historic inn—and ale house—Hopkin’s Ordinary makes for a fantastic place to stay the night.

Bristol

Half in Virginia, half in Tennessee, Bristol is known as the town quite literally cut in two by the state line. This corner of the South has also been putting country music on the map since the early 20th century when talent scout and music producer Ralph Peer traveled to Bristol from New York City to record the songs coming out of the area’s hills and hollers. The most famous of those 1920s recordings, called the 1927 Bristol Sessions, were those of A.P. Carter and his family, of whom the legend, and reality, still loom large around Bristol today.

Start at the Smithsonian-affiliated The Birthplace of Country to immerse yourself in music history. Stroll Bristol’s State Street, divided by the Virginia-Tennessee state line, and explore a vibrant tableau of storefronts, lunch counters, and restaurants. Stop at gems like Willow Creek Antiques and Cheap Thrills Records, and grab a bite at mid-century-styled Burger Bar or Blackbird Baker for dessert. 

Return to music in the evening at local venues like The Paramount. Make the 35-minute drive to the Carter Family Fold in Hiltons, Virginia. Part museum, part concert venue, and part dancehall, it doesn’t get more country, local, or authentic. Members of the Carter family introduce the evening, rock their grandchildren to sleep on the stage, and encourage the audience to join in the dancing. Stay at the in-town Bristol Hotel or at the luxurious country inn, Nicewonder Farm and Vineyards.

Charlottesville

Charlottesville is known as the home of the University of Virginia, which has one of the most beautiful campuses in the South, but the town also stands on its own, thanks to its charming downtown and surrounding countryside. Start your weekend on campus exploring the interior of the Rotunda and walking the grounds. Remember to look into the dorm that once housed a young Edgar Allen Poe and visit the university’s cemetery, which dates back to 1828. From the campus, make your way to Monticello, Thomas Jefferson’s sprawling estate, to learn about the Renaissance man and his complicated legacy.

When you’ve had your fill of history, shift to filling your glass and sample the local terroir at vineyards like Pippin Hill Farm and King Family, which are noteworthy both for their grapes and their views. For a casual lunch, stop at student-favorite Bodo's Bagels or head to Dairy Market, the sprawling food hall in town with local options galore. Opt for dinner at 1799, the restaurant at The Clifton, once the home of Jefferson’s daughter and now one of the area’s best places to stay. If you’re looking to stay closer to the university, it doesn’t get better than Oakhurst Inn, a boutique hotel located right next to the UVA campus.

Meadows of Dan

In the heart of the Blue Ridge Mountains, Meadows of Dan stuns with natural beauty at all times of the year. Most know of this countryside—just 30 minutes north of the North Carolina state line—thanks to Primland, a mountaintop report that stretches across 12,00 acres. Arriving at Primland feels like arriving at a private grand estate that has been around for generations, even though it was only built in 2009. Explore the wilderness on the many hiking trails and ATV paths or during an afternoon of clay shooting. The highlight of a visit here is Primland’s observatory. The state-of-the-art facility allows for inspiring views of the night sky and includes lessons from a resident astronomer.

While soaking in the Blue Ridge views and grounds makes it hard to leave Primland, outside the resort’s gates you’ll find the town of Meadows of Dan with its can't-miss sweet shop, Nancy’s Candy Co., and nearby market and lunch counter, Poor Farmer’s Country Store.

Orange

Escape to Orange for award-winning wineries, abundant history, and a rich food scene. Make your home base the Inn at Willow Grove, a tried-and-true historic inn with gorgeous views of the Blue Ridge Mountains. The hotel was one of the leaders in establishing the county’s Edna Lewis Menu Trail, which honors one of the greats of Southern cooking, Edna Lewis. One of the first African-American women to write a cookbook that didn’t conceal her race or gender, Lewis is celebrated throughout the area. Sample your way through her cuisine at restaurants including the BBQ Exchange, Spoon & Spindle, and Gordonsville Ice House.

When you’ve eaten your weight in barbecue, spend a few hours at James Madison’s Montpelier. As the home of one of both the United States and Virginia's founding fathers, Montpelier offers a view into Madison's life, legacy, and role in shaping the country. The house's powerful exhibit Mere Distinction of Colour shines a light on the story of the enslaved workers at Montpelier. Stop by the Orange County African American Historical Society, too.

Later, make time to sample the award-winning wines at Barboursville Vineyards and Horton Vineyards. Shop the best of the area’s vintage clothing and quilts at Folkling in the charming town of Gordonsville and garden and home goods at the beautiful and expansive The Market at Grelen.

Alexandria

Just across the Potomac River from the nation’s capital, Alexandria feels distinctly unique from Washington, D.C. As one of the oldest cities in America, the town is brimming with 18th-century history and charm. Soak it in with trips to historic house museums like the Lee-Fendall House and Carlyle House. No visit to the town is complete without a stroll on King Street, the pedestrian thoroughfare that leads down to the water. Stop in at the Torpedo Factory Art Center, a former torpedo factory-turned-lively space for working artists’ studios and shops, and Old Town Books, a small, but well-stocked bookstore housed in a former bank (complete with an existing bank vault).

If you’re lucky enough to have good weather during your visit, head out to the river for a sunset tour aboard the tall ship Providence. Grab lunch at local favorite Virtue Feed & Grain and dinner at Josephine, which brings the romance of a French bistro to a former firehouse in Alexandria’s Old Town. End the evening upstairs at Bar Jo with a nightcap.

Make time to venture out to George Washington’s Mount Vernon, which is just 20 minutes away—a visit to the former home of America’s first president is something to add to your bucket list. For the weekend, base yourself at the centrally located, historic Morrison House Hotel or the design-focused Hotel AKA Alexandria.

Bath County

West of the Shenandoah Valley and deep in the Allegheny Mountains, Bath County has been a four-season destination for generations, thanks to its natural mineral springs, rural vistas, historic retreats, and fly fishing. Back in the 18th century—1761 to be exact—an octagonal bathhouse was erected for locals and visitors to bathe in the mineral springs, making it America’s very first spa structure.

Since then, different iterations of the bathhouse have been built, and today you can enjoy the waters from the comfort of the historic Omni Homestead Resort. The hotel has been in operation for over 250 years and has welcomed an impressive 24 American presidents. Through the years (and a recent $140 million renovation), it has remained one of the country’s most beloved resorts. It’s far from the only place to stay in Bath County, however. The Fort Lewis Lodge & Farm mixes luxury and rustic charm on its 3,300-acre property. Base yourself here for a weekend of quiet swimming, stargazing, and country walks.

Whether you’re a seasoned fisher or eager to take your first lesson, it would be a shame to come here without indulging in the county’s pastime. For some guidance, local experts like Matt Miles or Wesley Hodges will show you the ropes. Don’t leave without stopping by Troddenvale at Oakley Farm, a National Register of Historic Places site renowned for its cider made with homegrown apples. 

Front Royal and Shenandoah National Park

Front Royal is known to many as one of the main routes into Shenandoah National Park, but it's a destination in its own right, too. The town is full of mid-century nostalgia. Its main street and roadside motels and attractions harken back to the tourism boom of the late 1930s when Skyline Drive was first extended into town. One spot, The Catamount Lounge, which opened in 2023, is embracing that throwback feeling. The cocktail lounge is an intimate space with retro decor and classic American cocktails and light bites. It’s a good place to spend an evening after spending the day hiking Shenandoah, cruising Skyline Drive, or visiting nearby Luray Caverns. Skyland and Big Meadows Lodge, the comfortably rustic lodges within Shenandoah National Park, can’t be beat for overnight stays in the area.

Rocky Mount

Less than an hour south of Roanoke, Rocky Mount never disappoints for a weekend trip. The small town offers it all: a walkable downtown, great restaurants and breweries, and a lively music scene. That’s a lot, especially considering the year-round population hovers around only 5,000. Rocky Mount might be best known as the gateway to The Crooked Road, the state’s heritage music trail. The Crooked Road guides you through the area’s rich bluegrass music heritage with information panels along the route that provide instructions on how to listen to audio recordings about each stop’s musical history.

Rocky Mount is also known for its current local music scene. Grab a ticket to a show at the Harvester Performance Arts Center, or opt for something more casual at bars that double as music venues, like The Alley Cat. Rocky Mount’s county, Franklin, is known as the Moonshine Capital of the World, so no visit is complete without sampling the local libations. Twin Creeks Distillery is a great place to wet your whistle. While Rocky Mount has some big hotel options, opt for a stay at one of the area’s historic inns, like The Claiborne Bed and Breakfast or the Early Inn at the Grove.

Williamsburg

Named one of the friendliest cities in the South, with a delightfully festive holiday season, Williamsburg has lots on offer. Step back through time to the days of the American Revolution at Colonial Williamsburg. The 301-acre living history museum has historic gardens, art museums, and dozens of historic sites and activities that tell the story of the country’s earliest days. You can tour an actual palace or fire a flintlock musket on the range. Be sure to also drive 30 minutes southeast to see where the Continental Army won the Revolution at the Yorktown Battlefield. After dark, test your mettle on a colonial ghost tour, or, if you’re feeling particularly brave, a ghost hunt. 

Of course, there’s plenty to do in Williamsburg for the more modern-minded visitors. Grab a sandwich for lunch at The Cheese Shop. Kick back at one of the wineries, breweries, and distilleries on the Williamsburg Tasting Trail. Enjoy live music and a Sauvignon Blanc at Saudé Creek Vineyards, mull over a classic lager at Billsburg Brewery, or learn how mead has been made from honey for millennia—and sample a flight—at Silver Hand Meadery. Or, avoid the Loch Ness Monster and ride a rollercoaster through Europe at the Busch Gardens theme park. Stay near both the park and Colonial Williamsburg at the Westgate Historic Williamsburg Resort or book a room at the charming Williamsburg White House Inn.

Chincoteague Island

On the tip of the Eastern Shore, Chincoteague Island easily earns its title as one of the prettiest beach towns in the South. Base yourself at the Anchor Inn on the waterfront or at the Island Resort Inn. Hop on the 50-cent Pony Express trolley throughout the summer and fall, and explore local parks and the historic downtown. For literary folks, enjoy afternoon tea at Miss Molly’s Inn, where Misty of Chincoteague was written. Order clam chowder, oysters, or the seafood boat at Captain Zack’s Seafood, or chow down on a shrimp taco from Pico Taqueria. 

Plan to spend time at the Chincoteague National Wildlife Refuge. The refuge’s dunes and salt marshes are a birder’s paradise with species like bald eagles, terns, songbirds, and various waterfowl migrating in and out throughout the year. The refuge is also a home for monarch butterflies and famed wild Chincoteague ponies. In addition to bird-watching, you can also hike, bike, fish, paddleboard, comb the beach for shells, and more at the refuge.  

Also, sail around Chincoteague and nearby Assateague Island on a wildlife boat cruise, where you can spot many of the creatures that call this patch of paradise home, including dolphins and wild ponies. For an extra-special trip, visit in July when local firefighters, known as the “Saltwater Cowboys,” round up a wild herd of Chincoteague ponies on Assateague Island and guide them across the watery channel to Chincoteague during the annual Pony Swim.