5 Must-Visit Wineries on the Monticello Wine Trail

The sun is setting over the Blue Ridge Mountains; you’re holding onto a glass of some of the best American-made Viognier, and there’s relaxing live music serenading the chill atmosphere. This is every wine aficionado’s ideal moment. And it’s possible by taking a trip down the famed Monticello Wine Trail in Charlottesville, Virginia – aka., “The Birthplace of American Wine.”

The Monticello Wine Trail is a network of over 35 wineries around Charlottesville. The trail pays homage to the vision of one of America’s Founding Fathers, Thomas Jefferson. While living in Monticello, he dreamed of positioning Virginia as a hub for the best American wine—a dream realized after his lifetime thanks to the Monticello Wine Trail.

Whether you’re passing by C-Ville (dubbed the “Hook” for its ability to, well…hook you to its offerings) or you plan to relocate to the beautiful city, make sure you pay a visit to the following wineries on the Monticello Wine Trail.

Cunningham Creek Winery (CCW)

Located 10 minutes from Charlottesville, the Cunningham Creek Winery is arguably one of the best places to hang out with friends and family over a great selection of wine. As a family-owned business, CCW focuses on the nitty-gritty—from the finely crafted French wine varietals, friendly hosts, lovely setting to safety measures.

Cunningham Creek Winery is a relatively new winery, having opened its doors to enthusiastic tasters in 2016. But even in its infancy, oenophiles will appreciate the winery’s vinification expertise. (PS: Their 2017 Meritage & 2017 Estate Petit Verdot won the 2020 Virginia Governor’s Cup Gold Medals!)
Based on online reviews by users, CCW is an ideal place for the family—including you’re four-legged friends (i.e., it’s a dog-friendly winery). 

They also host live music events in their expansive outdoor seating place, which offers good social distancing.

Tasting Price: Private tasting at $22 per person, including a private tour.

Address: 3304 Ruritan Lake Road, Palmyra, VA 22963 (Tel: 434-207-3907).

Jefferson Vineyards

If you’re a sucker for rich history like us, a visit to the Jefferson Vineyard is a must—and we bet you can already guess the reason why from the name of the estate! This is the exact location that Thomas Jefferson and Philip Mazzei (Italian winemaker) laid the groundwork to making Virginia the birthplace of American wine.

Jefferson Vineyards is owned and run by the Woodward family, which does an admirable job of honoring the Founding Father’s vision. It boasts a diverse portfolio of award-winning hand-crafted wines to excite your palate.

The estate is complimented by an awe-inspiring setting characterized by rolling hills and lush green forests. Pop up at the Jefferson Vineyards and sample some of their highly awarded Viognier. Chardonnay, Riesling, Rose, Cabernet Franc, or Petit Verdot.

Tasting Price: $12 per person for a classic tasting or $25 per person for a private tasting.

Address: 1353 Thomas Jefferson Parkway, Charlottesville, VA 22902 (Tel: 434-977-3042).

Veritas Vineyard and Winery

Veritas is arguably the most charming establishment on the Monticello Wine Trail. The family-owned estate’s seating areas are as cozy and homey as they get. There’s a relatively expansive lawn for the whole family (pups included), a huge picturesque tasting room, picnic table-style porch, a fireplace, and cozy couches, among other amenities that make the atmosphere welcoming.

Veritas offers a wide variety of wines—including an award-winning 2017 Petit Verdot, Viognier, Merlot, and Rose, to name a few. You can also sign up for site tours to experience every step of the captivating vinification process.

Tasting Price: $10 per person.

Address: 151 Veritas Lane, Afton, VA 22920 (Tel: 540-456-8000).

Pippin Hill Farm & Vineyard

Farm-to-table dining, anyone? Pippin Hill Farm and Vineyard is big on sustainable viticulture. The winery pairs their award-winning wines with ‘elevated cuisine’ – sourced from local farmers and their own Chef’s Garden. The Tasting Room menu highlights how the ingredients in your scrumptious meal were grown and harvested to take the dining experience up a notch.

The winery wins you over even before you enter the property. From the breathtaking view of the Monticello Wine Trail, grapes hanging from vineyards around the entrance, a pretty flowering hedge, to a spectacular patio dining area lined with bistro lights. And once you’re in, you get a chance to sample exquisite craft winemaking from the renowned Michael Shaps.

In a nutshell, Pippin Hill is the place to go for an all-around experience.

Tasting Price: $10 per person.

Address: 5022 Plank Road, North Garden, VA 22959 (Tel: 434-202-8063).

Barboursville Vineyards

Like the Jefferson Vineyards, Barboursville Vineyards is rich in history. It’s nestled on an 18th-century estate that was home to Virginia’s former Governor, James Barbour (1812-1814). For a walk down history lane, you can take a tour of the ruin of Governor Barbour’s old mansion—which so happens to be the architectural work of Thomas Jefferson.

Barboursville is also revered for its expansive wine tasting selection. There are around 20 wine tasting to appease your palate. But if you’re short on time, don’t miss out on their signature Octagon wine blend.

Tasting Price: $7 per person.

Address: 17655 Winery Road, Barboursville, VA 22923 (Tel: 540-832-3824).