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Grapes on a vine.

Spend V-Day Weekend at the Monticello Wine Trail


With 33 wineries sprinkled about the countryside just outside Charlottesville, VA, the Monticello Wine Trail has all the ingredients for a fun-filled Valentine’s Day weekend. The roughly two-hour drive from Alta Citizen transports you and your significant other to the relaxing, romantic weekend of your dreams.

Dubbed the “birthplace of American wine,” the Monticello Wine Trail is the realization of Thomas Jefferson’s dream of vineyards lining the rolling hills surrounding his famed Monticello home. More than 200 years later, that vision is very much a reality – and it’s yours to enjoy this Valentine’s Day weekend. Here are some of Alta Citizen’s favorite spots along and around the trail.

Wineries to Visit

Barboursville Vineyards

Barboursville is a staple on all the best-of lists. Rich in history, this winery is set on the estate of James Barbour, Virginia’s governor in the early 1800s. Visit the tasting room, tour the winery, indulge in rare vintages in the Library 1821 tasting room, or dine at the onsite Palladio Restaurant. You can even book a suite at the estate’s historic inn or in one of its cottages. Barboursville’s flagship wines include the Octagon, a Bordeaux blend, cabernet franc, and nebbiolo.

Jefferson Vineyards

Jefferson Vineyards is another winery deeply rooted in history. Set on land Thomas Jefferson and close friend Philip Mazzei, an Italian physician, grew grapes on more than two centuries ago, this charming estate is known for its variety. Its offerings include viognier, merlot, cabernet franc, petit verdo, and petit manseng. Bring a lunch and make an afternoon out of it. Or book a room at Colle, a six-bedroom historic home on the property, and stay the weekend.

Blenheim Vineyards

You’ve heard his music. Now try his wine. Iconic rocker Dave Matthews built Blenheim Vineyards with sustainability in mind. Its elegant tasting room was crafted with reclaimed wood and requires no electricity to light in the summertime. Oh, and the wine isn’t bad, either. Choose from viognier, chardonnay, cabernet franc, cabernet sauvignon, and petit verdot.

Where to Stay

The Inn at Monticello

Set on wooded farmland, this bed and breakfast is brimming with Victorian charm. Enjoy breakfast around the dining table every morning at this stunning country retreat. You’ll be close to all the stops on the Monticello Wine Trail as well as to Charlottesville’s many attractions.

200 South Street Inn

This Victorian-era bed and breakfast puts you close to the best of the Monticello wine country and Charlottesville. Its elegantly appointed rooms and delicious continental breakfast spread will help you rest and fuel up for a busy day on the trail.

The Inn at 400 West High

This eccentrically decorated boutique bed and breakfast is bright and modern. Although the house dates back to 1900, it’s been renovated twice in the past 20 years. You’re a short drive from both the Monticello Wine Trail and downtown Charlottesville, giving you the best of both worlds. And the full breakfast and always-available tasty baked treats are to die for.

Where to Dine After (or Before) the Wine

Fleurie Restaurant

The romantic Fleurie Restaurant was named one of Wine Enthusiast’s 100 Best Wine Restaurants in 2018 and features an inventive menu with upscale cuisine, including the ever-popular butter poached lobster.

C&O Restaurant

C&O Restaurant is another choice that’s big on romance. Across from the old Chesapeake & Ohio train station, this elegantly appointed restaurant offers standout entrees crafted with locally sourced ingredients. Highlights include the glazed duck breast and New York strip steak with bordelaise sauce.

Michie Tavern

Just down the street from the Inn at Monticello, the highly rated Michie Tavern serves up hearty Southern food in a rustic setting. Southern fried chicken, smoked pulled pork barbecue, and baked chicken are a few of the menu highlights at this popular lunch spot. 

Choose Your Own Adventure

When it comes to the Monticello Wine Trail, there are no bad options. To plan your own wine country adventure, visit the trail’s website and plan your route.

See the Alta Citizen blog for life hacks and fun things to do in the Newport News, VA, area.

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