Sip Your Way Along the Monticello Wine Trail in Charlottesville & Albemarle County, Virginia, USA

The Monticello Wine Trail, the trail that connects the Charlottesville area’s 40-plus wineries, continues to become more established and well-known each year — and it’s producing wines that are making oenophiles from all around the country and the world take note. In fact, the region was named 2023’s “Wine Region of the Year” by one of the world’s leading wine publications, Wine Enthusiast.

The Charlottesville area is situated at the foothills of the scenic Blue Ridge Mountains, a 2.5-hour drive from Washington, DC and conveniently connected to the greater Capital Region by Amtrak train service. Though Jefferson himself attempted to grow his own grapes here hundreds of years ago, it wasn’t until more modern times that these efforts were successful. The terroir in the Charlottesville area is well suited to growing a variety of grapes and the wines have been racking up the accolades regionally, nationally and even internationally, making now the perfect time to visit the Birthplace of American Wine.

Discover a more intimate setting at one of the many boutique wineries that dot the landscape or enjoy a glass at one the larger vineyards like Pippin Hill Farm & Vineyards or King Family Vineyards — and soak in epic views of the surrounding mountains while you sip. Transport to a warmer place while pairing wine with fine chocolate in a tropical conservatory at Glass House Winery. Or discover your new favourite chardonnay at Blenheim Vineyards — owned and operated by none other than world-renowned musician Dave Matthews of the Dave Matthews Band.

Ride in style on four wheels and let one of our many transportation companies do the work. They’ll plan the perfect itinerary for you and transport you to multiple wineries, meaning all you have to do is sit back, relax and decide which wine you’re going to order at the next location. And if wine isn’t your leisure beverage of choice, the Charlottesville area is also home to a variety of craft breweries, artisanal cideries and even a few distilleries.

After savouring award-winning wines at beautiful wineries, enjoy Albemarle County’s abundant outdoor recreation options. Take a hike and explore the broad, even paths that make up the Saunders-Monticello Trail, meandering up to the visitor centre at Monticello. The scenic Highland Rustic Trails can be easily accessed from James Monroe’s Highland, the historical property of the fifth president of the United States. Thomas Jefferson’s Monticello and James Monroe’s Highland are no more than a 5-minute drive apart. Then enjoy a scrumptious lunch at nearby Michie Tavern, a Colonial eatery dating back to the 1780s serving American Southern classics like fried chicken, stewed tomatoes and black-eyed peas. Don’t leave without trying the peach cobbler.

For more outdoor adventures, walk alongside one of the region’s local rivers or jump in on a kayak. The Rivanna River is lined with gently rolling trails and is a popular kayaking and tubing destination in the summer months and now in the winter months, you can sweat in the sauna and take a cold-water plunge in the river afterwards. In southern Albemarle County you’ll find the town of Scottsville, a lovely historical town situated on the bank of the James River. While kayaking and tubing are popular, you can let James River Batteau Company do the work for you while you enjoy a relaxing float on the river in a batteau, a historical flat-bottomed boat.

Staying in Charlottesville and Albemarle County is also a convenient way to explore Shenandoah National Park, famous throughout the world for its gorgeous, forested slopes and long scenic hikes, just a 25-minute drive from Charlottesville’s city centre.

After enjoying the countryside, be sure to allow enough time to visit The Rotunda and Academical Village at the University of Virginia, as they are a UNESCO World Heritage Site in conjunction with Monticello.  Walk along the Lawn and stop by the room formerly inhabited by Edgar Allan Poe, a legendary American writer. Near the Rotunda and Academical Village is the new Memorial to Enslaved Laborers, which honours the work and individual lives of the African Americans who laboured at the university.

When it’s time for dinner, you’ll find out why the Charlottesville area was recognised as one of America's next great food cities by Food & Wine. The historical pedestrian Downtown Mall in Charlottesville's city centre boasts farm-to-table restaurants at every turn and features many eateries with outdoor dining. Enjoy live music while you eat, or experience performances in a historical venue like the 90-year-old, architecturally stunning Paramount Theater.  Wrap up the night at one of many places to stay, from resorts, inns, bed and breakfasts, chain hotels, winery stays and holiday rental homes and gear up for another day of exploring Charlottesville and Albemarle County.

Start planning your stay today at visitcharlottesville.org or request your free visitor guide.