Just a half an hour outside Washington, D.C. — driving through one of many small towns in Virginia — the terrain was already beginning to feel like home. Through my window I caught views of green rolling hills, wooden-fence remnants from the Civil War battlefields, the faint scent of honeysuckle, and horses — one rolling joyously on its back soaking up the first rays of summer.
I grew up in these parts, not far from the Mason-Dixon line, and intimately understand why Virginia is a great place to visit. My driver, naturally, has no idea (his assumption, I learn later, is that I’m from California), and so I revel in his tales of the area.
“Jackie Kennedy had a horse farm (Glen Ora) here, and used to leave the White House to come out here and ride. Of course, some of Virginia’s best wineries are here too. [Former] First Lady Michelle Obama loved this one,” he slows to point out Greenhills Vineyards. “Be sure to try the sparkling wines.”
As reference to the dialogue, “here” is Middleburg, Virginia, America’s horse and hunt country capital. It’s home to chic boutiques, a leafy main street, scores of wineries and craft breweries, and (my primary reason for returning) the Salamander Resort & Spa.
Middleburg is just one of many best small towns in Virginia that remain under-the-radar but are worthy of a visit. From the Blue Ridge and Allegheny mountains to Shenandoah Valley to natural hot springs and tranquil coastline, here are a few of the Virginia towns we love.
Meadows of Dan
The Vibe: Untouched Wilderness
The 469-mile Blue Ridge Parkway connects Virginia’s Shenandoah National Park to North Carolina’s Great Smoky Mountains — two dazzling East Coast National Parks worthy of exploration. It is a glorious drive of mountains, meadows, fly-fishing streams, and untouched wilderness. It is only at milepost 178 where, seemingly out of the heavens, there comes a tiny Virginia mountain town: Meadows of Dan, population 72.
Visitors are greeted by a sign, aptly stating, “A simpler place in time.” This small town in Virginia is named for the waving meadows near the banks of the Dan River which flows through the area, and is known for its hiking trails, historic Mabry Mill, Nancy’s Candy Co. (try the artisan truffles), and in recent years, Primland Resort.
- Things to Do: Hiking, Mabry Mill, Poor Farmers’ Market, Nancy’s Candy Co.
- Places to Eat: Chateau Morrisette Restaurant, Longfin Grill, Jane’s Country Cafe
- Getting There: Meadows of Dan is a 90-minute drive from Roanoke, Virginia, and Winston-Salem, North Carolina.
The Stay: Primland Resort ($700+/night)
There is only one hotel in town, and it is stellar: five-star Primland Resort. Set on 12,000 private acres, the resort — hidden among towering trees — features romantic treehouses, log cabins, and an exquisite lodge. Fish the freshwater streams, hike or mountain bike the rugged trails, and slip into the dreamy Auberge Spa. Primland became part of the Auberge Collection in 2021, so expect a top spa experience. End the day with dinner at Elements, featuring fresh, seasonal dishes like North Carolina grouper over heirloom grits, followed by stargazing at the property’s onsite observatory.
The Vibe: Serious Horse Country
Although it occupies only six blocks, Middleburg (population under 1,000) is home to chic boutiques (Chloe’s, Zest), raffish men’s stores (Highcliffe), art galleries (Byrne Gallery), and superb cafes and restaurants. Try the new Tremolo, and classic tavern at the Red Fox Inn, one of the oldest continuously operating inns in the U.S.
Listed on the National Register of Historic Places, this very old and very small town in Virginia (established in 1728), is most known for its beautiful thoroughbred horse farms and noteworthy boutique wineries including the aforementioned Greenhill Vineyards, and Boxwood, focusing on Bordeaux-style blends. The town’s Film Festival has also become a major stop on the Oscar trail.
- Things to Do: Wine tasting, shopping, gallery hopping, annual film festival
- Places to Eat: Tremolo, Red Fox Inn, King Street Oyster Bar
- Getting There: Middleburg is a 40-minute drive from Washington DC; a one-and-a-half-hour drive from Baltimore; and three hours from Philadelphia.
The Stay: Salamander Resort & Spa ($600+/night)
The brainchild of BET-founder Sheila Johnson, Salamander Hotels & Resorts opened in 2005. It extends Johnson’s portfolio, which now includes properties in Charleston (Hotel Bennett), Tampa Bay (Innisbrook), Jamaica (Half Moon), Anguilla (Aurora), and Aspen (Aspen Meadows).
It was Johnson’s daughter, an accomplished equestrian, who led her to Middleburg, but it was her own deep passion for healing that led to the creation of Salamander Resort & Spa. The resort is a stylish three-core spa, equine, and culinary experience. Spend time with the horses, experience the rasul, a private translation of the traditional hammam, followed by a massage and dine on fresh meals, locally sourced with a glass of sparkly white Virginia wine.
The Vibe: Laid-Back Virginia Coastal Town
One of Virginia’s earliest settlements, white-picket-fenced Irvington (population 398) lies on the shore of Carter’s Creek and the Rappahannock River. This Virginia coastal town is located in the state’s Northern Neck peninsula, bringing centuries of history and watermen traditions. Observe osprey, eagles, and herons along Carter’s Creek; watch sailboats racing; savor Rappahannock River oysters and Chesapeake Bay blue crabs; and tour the Steamboat Era Museum — preserving Irvington’s history as a steamboat town during the late 1800s.
- Things To Do: Steamboat Era Museum, Historic Christ Church, water sports, beach lounging
- Places to Eat: Dredge, The Local, Fish Hawk Oyster Bar
- Getting There: Irvington is a one-hour drive from Richmond, and a two-and-one-half-hour drive from Washington DC.
The Stay: The Tides Inn ($425+/night)
Located on a private peninsula leading to the Chesapeake Bay, the Tides Inn (originally established in the 1940s) fosters connections to the people, history, land, water, and wildlife of the Northern Neck region. Explore the role Eastern oysters play in the ecosystem with the resort’s resident ecologist, relax in tranquil, recently refreshed rooms and suites overlooking the water, and join one of the chefs to learn how to clean and shuck freshly caught oysters.
The Vibe: Historic Village with Michelin Stars
With a population of less than 150, Little Washington is a small town in Virginia that verges more on village. Located in the eastern foothills of the Blue Ridge Mountains near Shenandoah National Park — a haven for hiking — this teeny Virginia mountain town is listed on the National Register of Historic Places. The Main Street of this movie-set village comes with sophisticated shops and cafes, but the shining (Michelin) star is worn by the Inn at Little Washington, which is easily one of the best hotels with good restaurants in Virginia (and arguably in the United States).
Established in 1978 by chef-owner Patrick O’Connell, the inn became the first and only 3 star Michelin restaurant in the Washington D.C. metropolitan area. Chef — who describes his classical French technique and style as a “romantic dinner party in a private country house from another era.” There’s a fully vegetarian version of the tasting menu, however, and the wine cellar, some 14,000 bottles deep, routinely wins the Wine Spectator Grand Award.
- Things to Do: Hiking, winery tours, shopping, gallery hopping
- Places to Eat: Inn at Little Washington, Clyde’s Willow Creek Farm, Magnolias at the Mill
- Getting There: Little Washington is a half-hour drive from Luray, and an hour-and-a-half drive from Washington D.C.
The Stay: The Inn at Little Washington ($800+/night)
Chef brings his artistry not only to the dinner plate but to the guest side of the property. With his own background in theater, O’Connell enlisted London stage and set designer Joyce Evans to spin magic to the hotel’s 23 guest rooms and suites, each sumptuous and dramatic, with Bulgari bath products and 24-hour room service — an exquisite art piece.
The Vibe: Restorative Healing Waters
Years ago, I bathed in the Warm Springs Pools (aka Jefferson Pools) in Hot Springs (population 738), a resort town in the Allegheny Mountains near the West Virginia border. My attire — historical and hysterical — was a one-piece white “bathing costume” given to me at check in. Hair spilling out of a makeshift bun, the white pantaloon-like suit baggy to mid thigh, I resembled a baby in an oversized diaper; I could not stop laughing. But once my body melted into the steamy, magnesium-rich hot springs, all hilarity was forgotten and I concluded this had to be one of the best small towns in Virginia.
Floating in the healing waters — four springs flow into the timbered octagonal bathhouse from the Allegheny Mountains, already heated — this Virginia vacation spot transported me back centuries. The Pools recently reopened following a major (14-month, $4 million) restoration by The Omni Homestead Resort (the historic bathing costumes retired, so bring your own for coed and family soaks). The baths remain one of the region’s most sought-after experiences, along with hiking, fly fishing, skiing, and perusing the ‘downtown’ shops for local art and treasures.
- Things to Do: Hot springs and bathhouses, hiking, skiing, fishing, shopping,
- Places to Eat: Sam Snead Tavern, Martha’s Market, Jefferson’s Restaurant
- Getting There: Hot Springs is an hour-and-a-half drive from Roanoke and Charlottesville, Virginia.
The Stay: Omni Homestead Resort ($350+/night)
Opened as an inn in 1766, the landmark Omni Homestead Resort, set on more than 2,000 acres, has hosted 23 US Presidents. Today’s visitors come for the golf, fly fishing, horseback riding, fine dining, fresh mountain air, and the spa of course, including the recently renovated mineral pools. Relax in the Serenity Garden, an exclusive outdoor, adult oasis which includes a geothermal rich in magnesium, potassium, and calcium.
Dine on fresh local ingredients at Jefferson’s Restaurant, featuring a farm-to-table approach with a selection of hand-picked prime and regional meats from Virginia; spend time learning about the state’s buzzing wine industry — select from distinct wine flights or wines by the glass at the tasting bar, and purchase a bottle to take home.
The Vibe: An Island Frozen in Time
Tangier Island (population 728) is a sliver of mud and marsh grass, but don’t let that fool you into thinking this isn’t one of the best small towns in Virginia. This U.S. coastal town is located approximately 12 miles from mainland Virginia smack dab in the middle of the Chesapeake Bay. There are no cars — residents make their way around the narrow streets in golf carts, bicycles, or on foot; there is only one school — kindergarten through 12th grade; and access to and from the island is solely by boat (or small plane). Considered one of the most isolated communities in America, Tangier Island is renowned for its soft shell crabs, and hard-to-pinpoint dialect.
Some contend the islanders’ accent — passed through generations — is Elizabethan English, others say Cornish, and still others say it is simply the residual of isolation. Reportedly, when the Civil War broke out, the island’s residents (mostly Methodists) chose not to join Virginia as members of the Confederacy and have remained separate since. Arrive by ferry, explore the history museum, watch the watermen at work, and enjoy the island’s famed crabs, and local ice cream.
- Things to Do: Tangier History Museum, watermen’s tour, bicycling, kayaking
- Places to Eat: Lorraine’s Seafood Restaurant, Fisherman’s Corner, Sandy’s Place
- Getting There: Onancock is an hour drive from Norfolk and Virginia Beach, and about three hours from Wilmington, Delaware, and Baltimore, Maryland. The ferry from Onancock to Tangier Island takes one hour each way.
The Stay: The Charlotte Hotel, Onancock ($150+/night)
With limited accommodations on Tangier Island, we recommend taking the 25-passenger ferry boat from Onancock, Virginia (runs May through September), and staying at the intimate Charlotte Hotel. Although constructed in 1907 as the ‘White Hotel, the building currently housing The Charlotte had not operated as a hotel for more than 60 years when it was purchased by Charlotte and Gary Cochran.
Today, the boutique property features eight guest rooms, a highly regarded restaurant, full-service bar, and loads of artistic touches, starting with its green exterior and French doors flanked by chic little topiaries, and interior original artworks by Charlotte, also an artist.
The Vibe: Oysters and Wild Horses
Also close to Onancock (just 30 minutes away) is the town and island of the same name, Chincoteague (population 2,900). Originally settled in the 1700s, the town became a household name thanks to the 1940s publication of Misty of Chincoteague, a story about one of the island’s now-famous wild ponies.
Stroll the quaint downtown, dine on the island’s famous oysters, and enjoy the pristine beaches. The major highlight is, by far, the wild horses. Chincoteague is the gateway to the Chincoteague National Wildlife Refuge on Assateague Island — one-third of which resides in Virginia; the other two thirds in Maryland. Assateague Island is literally home to hundreds of wild horses and ponies. Move about quietly and observe.
- Things to Do: Beach lounging, shopping, wild horse spotting, sunset cruises, water activities
- Places to Eat: Bill’s Prime Seafood & Steaks, Ropewalk Restaurant, The Village Restaurant
- Getting There: Chincoteague is an hour’s drive from Ocean City, Maryland; and three hours from Philadelphia, Baltimore, and Washington.
The Stay: A Private Waterfront Home ($425+/night)
Enjoy the magic of the sea horses from this stunning Waterfront Airbnb, a four-bedroom, three-bathroom home overlooking the bay and marshes. We especially love the light and airy interiors, oversized windows with water views, indoor fireplace, and new this season, a hot tub.