Country roads embroider Virginia’s rolling landscape, lacing together charming inns, beautiful wineries, and orchards in bloom.
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Pippin Hill Farm & Vineyards in Charlottesville, VA
Pippin Hill Farm & Vineyards is a culinary destination on the Monticello Wine Trail.
| Credit: Gabriela Herman

From its inviting spot in the Blue Ridge foothills, Charlottesville, Virginia, summons visitors every spring. When the days grow longer, the landscape explodes with color and the lemony scent of magnolias perfumes the air.

Around 100 miles southwest of Washington, D.C., and 70 miles northwest of Richmond, the state's capital, Charlottesville is perhaps best known as a thriving college town because it's home to the University of Virginia (UVA). While the Downtown Mall bustles year-round, the more pastoral scenery extending from the city's nucleus into rural Albemarle County is the big attraction when the earth warms enough to make way for a fresh carpet of butter yellow daffodils and delicate purple crocus.

"Charlottesville has a wonderful balance of urban and rural, to the point where you are never more than a 10-minute drive from rolling pastures or the foothills of the Blue Ridge," says Dan FitzHenry, COO of local favorite Grit Coffee. "In the spring, you can watch blossoms crawling up the mountains. Flowering redbuds and dogwoods in the tree-lined neighborhoods give the city a vibrancy that's hard to describe."

From farm-to-table culinary experiences and in-the-garden wine tastings to long strolls through picturesque fruit orchards, Charlottesville is rich with opportunities to revel in the natural beauty of the season. Here's our play-by-play guide to making the most of them.

The Clifton in Charlottesville, VA
The Clifton Hotel in Charlottesville, VA
Left: The Clifton is a boutique hotel with easy access to outdoor escapes in the Virginia countryside. | Credit: Gabriela Herman
Right: Credit: Gabriela Herman

Where to Stay

On the outskirts of Charlottesville, The Clifton occupies a manor house built in 1799 for Thomas Jefferson's daughter Martha and her husband, Thomas Mann Randolph. Now one of the area's most beloved inns, the house is ringed with lovely gardens and filled with gorgeous interiors. Guests are encouraged to wander around the grounds, preferably with an aperitif in hand—we suggest Memoirs of a Grapefruit, one of the inn's signature cocktails that features grapefruit, orange, and lime flavors.

Paths meander from the main house to the Garden Cottages and the Livery Stables, and each of them is hemmed with delicate flowers that spill over layered stones while pink dogwoods and tulip trees create colorful canopies around the property. The most stunning show of all is the peony garden. Some guests try to time their stays to catch it in bloom. A long breakfast (get the Farm to Fork Omelet) on the extensive veranda is a must here—as is enjoying dinner at on-site restaurant 1799. An infinity pool can also be found in the gardens overlooking the property.

One of Charlottesville's most prized resorts recently reopened after a long, meticulous renovation that took two years to complete. Built as a private estate in 1912, Keswick Hall is set on 600 acres and is tucked between bucolic horse farms and the Blue Ridge Mountains. Once owned by Bernard Ashley, widower of designer Laura Ashley, this destination was formerly known for its distinctive English Country aesthetic. New owners Molly and Robert Hardie set out to refresh the entire property while honoring its history, and the resort has been transformed with a more contemporary riff on traditional design. Rooms are all arrayed in soft creams and serene blues with Frette linens and toiletries by Red Flower, which are inspired by the scents of local grasses and blooms. Photographs displayed around Keswick Hall feature the hotel's beautiful setting as well as the Hardies' nearby farm, a nod to their desire to connect visitors with the landscape they love.

There's no better way to take in the views than to relax by the Horizon Pool overlooking the renowned Full Cry golf course. Or grab a seat at Marigold, the first Virginia outpost of famed chef Jean-Georges Vongerichten, where the dining concept revolves around seasonal offerings from the owners' farm. A patio just outside is lush with the restaurant's namesake flower. Guests are encouraged to linger over a craft cocktail and play a game of pétanque.

The Wool Factory in Charlottesville, VA
Public Fish and Oyster in Charlottesville, VA
Left: You'll find distinctive dishes at The Wool Factory, located in a historic neighborhood. | Credit: Gabriela Herman
Right: Public Fish & Oyster serves up plenty of fresh oysters. | Credit: Gabriela Herman

Where to Eat

Charlottesville is a town devoted to supporting area farmers, sourcing the finest ingredients, and eating very well. The Wool Factory may stand out as the best all-around example of this. Housed in the historic Woolen Mills area along Moores Creek is an enclave of exciting eateries. The Workshop serves Grit Coffee, which is revered in Charlottesville, and pastries from Cou Cou Rachou, the newest bakery helmed by Rachel De Jong (who was formerly the pastry chef at The Inn at Little Washington). Locals will warn you that their delicious ham-and-cheese croissants sell out early. Across the courtyard is Selvedge Brewing, a craft brewery with a full menu that takes bar food to the next level. Enjoy a Herringbone IPA, and be sure to try the slow-cooked Peruvian Chicken. Finally, Broadcloth stands out as an upscale (and weekends-only) haven for foodies. Chef Tucker Yoder changes the menu here often, showcasing what regional farmers are harvesting.

C&O Restaurant in Charlottesville, VA
Enjoy a meal on the patio at C and O Restaurant.
| Credit: Gabriela Herman

Over at Public Fish & Oyster, the lobster roll is a can't-miss meal, and the patio at C&O Restaurant is a prime spot for a romantic dinner out. Little Star also draws in diners with their unforgettable appetizers and entrées such as coal-roasted chicken with mint, basil, and parsley.

The Monticello Wine Trail in Charlottesville, VA
Pippin Hill Farm & Vineyards in Charlottesville, VA
Left: The Monticello Wine Trail includes 40 scenic stops. | Credit: Gabriela Herman
Right: Credit: Gabriela Herman

Don't Miss the Wine Trail

The topography of Albemarle County is ideal for grape growing, and the Monticello Wine Trail has 40 wineries in a 25-mile radius of Charlottesville. Pippin Hill Farm & Vineyards is known for its landscape, food, and wines and has verdant grounds, including a Kitchen Garden tended by certified horticulturist and head gardener Diane Burns. To take in the area's natural beauty, schedule enough time to wander the property, including the wildflower meadow, and then savor the food and wine. Although walk-ins are usually welcome on the lawn, reservations are highly recommended for table service.

King Family Vineyards in Crozet, VA
King Family Vineyards in Crozet, VA
Left: Take in the mountain views and wine at King Family Vineyards. | Credit: Gabriela Herman
Right: Credit: Gabriela Herman

King Family Vineyards is a destination winery too. Guests flock to the property for its signature Viognier and its gorgeous setting. Tucked into the Blue Ridge foothills in Crozet—a tiny town just outside Charlottesville—the winery has its own polo fields. Sunday matches begin in late May and run through mid-October. The lawn is ideal for picnics, and the market offers charcuterie and other bites to pair with your wine. Feel free to bring your own snacks, or come on Wednesdays, Saturdays, and Sundays when the estate hosts local food trucks.

Down the road in Keswick, Elizabeth and Guy Pelly recently moved across the pond from London to reinvent a storied farm as their new family home, tasting room, and vineyard. "We had come to the area for a wedding weekend and were excited by the idea of owning a piece of land here and turning it into something special," says Guy. The "something special" turned out to be Merrie Mill Farm & Vineyard. While Guy learned viticulture from the ground up, Elizabeth oversaw the restoration of the property's house and created its indoor-outdoor tasting room. She worked closely with Kemble Interiors to design a gathering space like no other in the region. "I filled it with curiosities, antiques, beautiful wallpapers, and one-of-a-kind pieces," notes Elizabeth, who recently procured an antique carousel with 10 cast-iron ponies. The expansive upper veranda with an unforgettable view of the grounds and surrounding mountains lures visitors to relax on a wicker love seat and unwind with a glass of wine.

A trip to Charlottesville wouldn't be complete without a front-porch bourbon sampling at Ragged Branch Distillery. Visit the tasting room—a picturesque farmhouse on a knoll—on a spring afternoon to have a sip of the handcrafted Virginia straight bourbon.

UVA Spring Blooms
Monticello in Spring, Charlottesville, VA
Left: Experience the UVA gardens in bloom. | Credit: Gabriela Herman
Right: Book a tour to learn about the history, house, and grounds of Monticello. | Credit: Gabriela Herman

What To Do In Town and Nearby

The grounds of the University of Virginia are as photogenic as its oldest buildings, famously designed by Thomas Jefferson. A stroll around the Academical Village is the perfect way to take in the campus. Marvel at the incredible yulan magnolia while it's in bloom on the northeast corner of the Rotunda.

Another stop is Thomas Jefferson's Monticello, where the grounds and historic gardens glow every spring with tulips in bloom. "From early April into late May, the colors here are simply extraordinary, featuring a dramatic succession of flowers," says Peggy Cornett, Monticello's curator of plants, who has 39 years of experience at the estate. "The 20 oval flower beds around the house are filled with hyacinths, tulips, lilies, crocus, and daffodils along with annuals such as larkspurs and poppies." Cornett suggests the Saunders-Monticello Trail, a beautiful, mostly shaded walk that shows off redbuds and a sea of native flowering dogwood trees. During your visit, guided experiences—including the Gardens & Grounds Tour, the Slavery at Monticello Tour, and the Hemings Family Tour—invite you to learn the stories of the free and enslaved people who lived and worked at the property more than 250 years ago.

Chiles Peach Orchard in Charlottesville, VA
Pick your own fruit during harvest season at Chiles Peach Orchard.
| Credit: Gabriela Herman

Then head to Chiles Peach Orchard, where rows of trees form tunnels of pink blooms. Five generations of the Chiles family have been harvesting fruit in Albemarle County for the past century. When the farm opens in April, visitors come to see the blossoming trees. They return throughout the growing season to pick produce and to try the famous peach ice cream and fresh cider doughnuts.

The Market at Grelen in Somerset, VA
Grelen Nursery in Somerset, VA
Left: Stop by The Market at Grelen for a cup of tea and a garden-themed browse. | Credit: Gabriela Herman
Right: Credit: Gabriela Herman

One of the area's other gems is Grelen Nursery in nearby Somerset. Set on 1,000 acres, this is one of the East Coast's premier suppliers of plants, shrubs, and trees, but it's also a hub for great food and outdoor experiences. In the spring, when the orchards are beginning to burst with color, you can walk the property's trails before browsing The Market at Grelen, a European-inspired shop and cafe. Enjoy dishes made with local ingredients (like the Oakland Chicken Salad Wrap or the Bloomfield Fig Sandwich) alongside Virginia wines and brews. The sunny patio is the ideal place to take in a view of the flowering trees, which are thoughtfully planted along the contours of the land. Be sure to save room for the market's ice creams, especially the flavors made with the property's own fruits, which you can pick yourself during the summer and fall.