Guide to Charlottesville's Route 29 Wine Trail

Explore Wineries Near Charlottesville, Virginia

The Monticello Wine Trail, nestled along VA Route 29, boasts 33 outstanding wineries, each offering its own unique charm. While it's impossible to enjoy all 33 in one day, I’ll spotlight two of my favorites along with a fabulous brunch spot.

Loving Cup Winery

Loving Cup Vineyard & Winery is a rare find as one of only three certified organic wineries on the East Coast! We enjoyed a warm and engaging conversation with Karl, the owner, who shared his passion for organic viticulture. It’s a small operation, with Karl and his father managing all aspects of the vineyard and winery themselves. Their dedication to organic practices means choosing disease-resistant grape varietals, as they don’t use common pesticides. Tastings are only $5, and you’ll sample five unique wines. My personal favorites? The Loving Cup White, Dudley Nose Rosé, and their delightful house-made Sangria! Loving Cup's dedication to organic farming makes it a standout experience on the Monticello Wine Trail.

Mountain and Vine

Previously known as Delfosse Vineyard and Winery, Mountain and Vine offers a sprawling property with breathtaking views and a collection of award-winning wines. Owners Adrienne and Mike were gracious hosts, even taking us on a charming tour around the vineyard in a "safari" vehicle. Beyond the wines, Mountain and Vine is a stunning venue for weddings and events, and there's even a cozy cabin on the property available for rental. My top picks from Mountain and Vine’s lineup include their 2022 Chardonnay, 2013 Merlot, and the award-winning Grand Cru Olivier, a blend of Cabernet Franc, Merlot, Petit Verdot, and Malbec. Tastings are $10, and with so many fantastic options, you’ll likely want a bottle to take home as a memento of your visit.

Brunch at Basic Necessities

This cozy spot is a hidden gem with a French-inspired twist. Basic Necessities' unassuming café vibe, paired with its delectable menu, makes it the ideal start to a wine getaway. Their Sunday brunch is a must; I enjoyed the French Toast with fresh fruit and a refreshing mimosa—perfect for the wine adventure ahead. While we didn’t sample the wines available, owner Kay’s expertise in French wines is evident, as is the café's charming gourmet wine and food shop inside.

Closing Thoughts

If you’re ready to dive deeper into the Monticello Wine Trail and the area’s other amazing wineries, visit Monticello Wine Trail

This particular article originally appeared in Katie Church’s WineandWeekends.com blog and has been updated to reflect the name change from Delfosse Vineyards to Mountaint and Vine. Read her full-length VA Wine Blog for a full 2-3 day itinerary!