I had never visited Virginia before our daughter went to college there, but over the past four years, I’ve completely fallen in love with it. There’s something special about Virginia’s landscapes—its rolling hills, charming small towns, and rich history. As her time in college comes to an end, we finally took the road trip we had always talked about to explore more of the state beyond our usual visits. With inspiration from an article about cozy Virginia inns, our trip took us through Lexington, Charlottesville, Middleburg, and Washington, VA, blending historic stays, beautiful countryside, memorable meals, and a new appreciation for Virginia’s wine scene.
Lexington
We began in Lexington, where our daughter attends school—a town that never fails to charm me with its brick-paved sidewalks, welcoming residents, and the breathtaking Shenandoah Valley. Over the years, I’ve stayed in several inns here and highly recommend the following:
Stonegate – Stonegate is a historic five-bedroom guest house dating back to 1832, just a short walk from downtown. Guests can unwind in tastefully decorated rooms, enjoy shared spaces like the library and screened porch, and start the day with a fresh breakfast prepared by co-owner Margaret Hutton. Fly-fishing enthusiasts will appreciate that her husband, Derek, is a skilled guide who knows Virginia’s most scenic fishing spots.
Thorn Hill Inn – Established in 1792 and listed on the National Register of Historic Places, this bed and breakfast has two houses on the property where guest rooms are located. Owners Bennett and Alyson Ross provide a warm, welcoming stay, with Alyson preparing a fresh breakfast each morning. I noticed that the link to their website was not working, so I am hoping they are still open for business. If not, I have included this link here to several inns in the general area.
The Georges – For our most recent stay, we chose The Georges for its proximity to the natatorium for the swim meet, and I truly enjoyed it. Heated towel racks, heated bathroom floors, luxurious beds, and a delicious complimentary breakfast made this stay a standout.
Where to eat in Lexington? The town is small, and I have eaten everywhere at this point. I recommend the following: Taps, Haywoods, Legendary Eats, Hardens, Zun Zun, and Heliotrope Brewery. The nearby hiking is amazing. Our daughter swears by the Devil’s Marbleyard, but it is not for the faint of heart (like me). She and Hubby also hiked House Mountain, which they loved.
WW2 Memorial and Virginia’s Wine Country
An hour southwest of Lexington is the small town of Bedford, VA, where a visit to the National D-Day Memorial was deeply moving, especially thinking about my father’s connection to WWII and fighting in the European theater. In the winter, the main water feature of the memorial was out of service, so Hubby and I made a mental note to come back in warmer weather. Nonetheless, it is at the top of our list of must visit places in VA.
Next, we made our way to Charlottesville and one of the prime areas for Virginia wine. Even in January, the scenery was stunning—the rolling hills and bare vines against the winter sky created a quiet beauty. Virginia’s wine heritage dates back to 1609, when Jamestown settlers planted vines, making it one of the oldest wine-producing regions in the U.S. Thomas Jefferson famously attempted to cultivate European grape varieties at Monticello (located near Charlottesville) but struggled with Virginia’s climate. Today, the state boasts over 300 wineries, carrying on a tradition that has thrived for centuries.
Wineries we visited included:
King Family Vineyards (Charlottesville) – Known for its Meritage blends and polo fields, where horses graze between matches.
Veritas Winery (Charlottesville) – A family-run estate producing elegant, old-world-style wines.
Trump Winery (Charlottesville) – Notable for sparkling wines and a tasting room with vineyard views.
Pippin Hill Farm & Vineyards (Charlottesville) – A picturesque estate where food and wine pair beautifully.
Greenhill Winery & Vineyards (Middleburg) – A boutique winery in horse country, specializing in Bordeaux-style wines.
Before I dive into my over-the-top birthday dinner, I would love to quickly cover some of the meals we enjoyed, plus some we hope to enjoy when we return. In Charlottesville, we had an incredible dinner at Public Fish & Oyster, the best sandwich (grilled portabella mushrooms with pimento cheese) at the Greenwood Grocery, and a lovely lunch at Marigold by Jean-Georges at Keswick Hall. I also hear that Tavola and Smyrna are local favorites. In Middleburg, we dined at the Night Fox Pub of the Red Fox Inn and indulged in more oysters at King Street Oyster Bar, both of which I highly recommend. If you are feeling naughty, order the Mile High Pie for dessert at King Street…and thank me later.
Memorable Inns, Meals, and Moments
Beyond the wineries, our trip was as much about the journey as the destination—including exceptional meals and some of the most charming small inns I’ve ever visited.
The Clifton (Charlottesville) – A boutique hotel set on 100 acres, with luxurious accommodations in late 18th- and early 19th-century buildings. Guests can enjoy walking trails, a private lake, an infinity pool, and farm-to-table dining at 1799, featuring ingredients from the property’s garden.
The Red Fox Inn & Tavern (Middleburg) – Established in 1728, this is one of America’s oldest continuously operating inns, known for its Virginia Hunt Country charm. It offers 22 uniquely decorated rooms, suites, and cottages, plus seasonal dining experiences in its tavern and Night Fox Pub.
The Inn at Little Washington (Washington, VA) – A visit to this Michelin three-star luxury country inn established in 1978 by Chef Patrick O’Connell has been on my bucket list for a while, and it did not disappoint. Originally a converted garage, it has since become one of the most celebrated restaurants in the country, earning the AAA Five Diamond Award for both its dining and accommodations.
A Birthday Dinner at The Inn at Little Washington
Before settling in to our room, we grabbed a quick lunch at Patty O’s Cafe, the smaller, more casual sister restaurant at the Inn. It was beautifully decorated, and the food delicious. I understand it is a big draw with locals, especially if you want to dine in a more relaxed (and less expensive) environment.
To celebrate a milestone birthday (DM me and I might divulge my age!), we splurged on a once-in-a-lifetime meal at The Inn at Little Washington—Virginia’s only Michelin three-star restaurant, an experience that exceeded every expectation. First, we lingered in the stunning Monkey Lounge, admiring the murals by artist Dana Westring, before sitting down and having an aperitif.
Once seated at our table, I chose The Good Earth menu, a beautifully crafted vegetable-forward tasting with exquisite wine pairings:
Chilled Borscht with Sour Cream Espuma and Dill with a Markus Molitor Riesling, Spätlese
Turnip & Black Truffle Tartare with Parmesan Croutons with a Domaine Pichot Vouvray
Fricassée of Potato Gnocchi with Chanterelles with Domaine Servin Chablis
Vegetable Tian on a Potato Rösti with Ratatouille Sacchettoni & Beurre Blanc With G.D. Vajra, Dolcetto d’Alba
Despite the abundance of courses, we had to order the cheese cart—not just for the cheese but also for the pure entertainment of meeting Cameron Smith, the Inn’s Cheese Whiz, a cheese aficionado who rolls in with a cow-shaped cart that moos. I thought I knew a lot about cheese until I met this guy. And much of his cheese was local Virginia cheese, so it was certainly an experience I had never had before.
Some beautiful desserts followed, along with a little history lesson about George Washington’s favorite fruit, the pawpaw.
Shenandoah National Park
Some of you might be curious if we visited Shenandoah National Park, conveniently located just a short drive from Charlottesville. Although the park’s lodges are closed in winter, we had the chance to explore it two years ago. The park boasts a beautiful section of the Blue Ridge Mountains, highlighted by the winding Skyline Drive, lush forests, and stunning waterfalls. We stayed at Big Meadows Lodge, a rustic retreat offering spectacular valley views, and hiked the Old Rag Circuit, one of the park’s most popular and challenging trails, featuring rock scrambles and expansive summit views. It was an unforgettable experience of Virginia’s natural beauty, and I would go back in a heartbeat. I dream of driving the Blue Ridge Parkway from Smoky Mountain National Park to Shenandoah National Park.
Fun Bit of Trivia Before I Sign Off: Why is Virginia called the Old Dominion
This very question came up at our daughter’s first conference meet, called the Old Dominion Athletic Conference Swimming Championships. It turns out that the nickname, Old Dominion, dates back to colonial times. King Charles II of England granted the title in recognition of Virginia’s loyalty to the English Crown during the English Civil War. Today, it reflects Virginia’s incredible history as home to Jamestown, the first English colony, and four of the first five U.S. presidents. There you have it…if you are in the “Virginia is for Lovers” camp, drop me a line below and tell me why! xoM
