Wineries to Visit on the Monticello Wine Trail

April 25, 2024  |  Chiswell Farm & Winery

Category: Local Guides  |  Tags: wine

In 2023, the Monticello AVA was named Wine Enthusiast’s Wine Region of the Year. This prestigious recognition comes at a time of momentum for Virginia wine: local winemakers’ understanding of the cool-climate terroir results in delightfully unique vintages and a blossoming community of wine lovers.

Aficionados with an affinity for California chardonnays and Tuscan Chiantis may ask: what makes Virginia’s wine so special?

To start, the area’s wine history dates back to the 1700s, when former President Thomas Jefferson spurred the beginning of American winemaking. While Jefferson’s attempts were nearly fruitless, recent generations are realizing greater successes.

The area’s bountiful vines of cabernet franc, petit manseng, petit verdot, and others are now hallmarks of the region. Many of the best wineries on the Monticello Wine Trail boast multiple award-winning wines of local competitions, including the annual Monticello Cup and Virginia Governor’s Cup.

2024 Monticello Cup silver medal wines

At the center of Virginia Wine Country is the Monticello Wine Trail, which connects over 40 wineries around Charlottesville. Member wineries share a dedication to crafting quality beverages and welcoming wine lovers to our beautiful state.

We’re proud to be members and share comradery with other family-owned wineries in the region. Of course, before we discuss some of the best wineries on the Monticello Wine Trail, we must introduce ourselves!

Chiswell Farm & Winery

Chiswell Farm & Winery is the most recent addition to our family of venues, joining Carter Mountain Orchard, Chiles Peach Orchard, and Spring Valley Orchard. Since opening in 2021, we’ve had the pleasure of welcoming visitors from near and far to our historic home-turned-winery in Greenwood, Virginia.

Having planted the first trees at Chiles Peach Orchard in 1912, our family is deep-rooted in the Crozet community. Now, our fifth-generation farming family has three generations actively involved in the production and distribution of locally-grown produce, including the wine grapes used by many of the area’s wineries.

One of the best parts of sharing our wine in this historic home is the unique spaces. Throughout the property, guests will find individual rooms where they can make themselves at home. It’s always a joy to see friends and family cozying up on one of the downstairs sofas or challenging each other to a chess game upstairs.

Five men sharing wine and snacks at Chiswell
Two women doing a sparkling wine toast at Chiswell

Of the many things that make Chiswell special, we take pride in our team’s creativity in developing different specialty drinks every season! As one of the few wineries in the area to do so, we’re always testing different combinations and finding new ways to enjoy our wines.

During the spring and summer of 2024, we’re mixing up a Strawberry Citrus Sangria, which features our rosé, lemon-lime seltzer, fresh strawberries, and a dash of mint.

Strawberry Citrus Sangria specialty drink

Septenary Winery at Seven Oaks Farm

Located three minutes from Chiswell

To find Septenary Winery, all you need to do is take a short trip down the road from Chiswell. Located on Seven Oaks Farm in Greenwood, Septenary is bustling with farm animals! Seven Oaks Farm sustainably raises free-range Pekin ducks and grass-fed cattle. While the livestock aren’t part of the Septenary Winery tasting experience, they are a testament to the Zimmerman family’s dedication to sustainable farming.

This commitment extends beyond livestock and translates into the family’s wine grape production, as well! Todd and Sarah Zimmermann founded Septenary to preserve and improve the fruits of their farmland. The Estate Vineyard is carefully placed to facilitate ample airflow, sunlight, and optimal growing conditions for seven acres of merlot, cabernet franc, petit verdot, syrah, and viognier vines. 

Three bottles of Septenary Wine
Vineyard at Septenary Winery

Pollak Vineyards

Located five minutes from Chiswell

Pollak Vineyards is the namesake of its founding family. Margo and David Pollak saw the potential to create quality wines in well-sited and meticulously maintained Virginia vineyards. This potential blossomed into their winery, which opened to the public in 2003.

We firmly believe that each vineyard’s wines capture unique qualities, from the caliber of the terroir to the grape harvesting methods, aging, and bottling experience. However, there’s something particularly distinctive about the wines at Pollak Vineyards. Pollak’s winemaking techniques are deeply influenced by European tactics, including those in France’s Bordeaux region. If rich and complex tasting notes characterize your dream glass of wine, then Pollak Vineyards is worth visiting!

Flying Fox Vineyard

Located eight minutes from Chiswell

Flying Fox Vineyards consistently produces a limited quantity of wines with the promise of consistency and premium quality. This portfolio features eight Virginia classics, including viognier, cabernet franc, and petit manseng. The winemaking team’s sharp focus on specific varieties encourages play outside the wine space. This is especially evident in the vineyard’s Vermouth production!

Flying Fox’s Vermouth label has four flavors, each highlighting the bounty of Virginia’s distinct seasons with botanical infusions. These Vermouths may be enjoyed neat or in a cocktail (or, as they call it, Fox-tail!).

Flying Fox vermouth
Flying Fox rose wine

Owners Emily Hodson, Elliott Watkins, Chloe Watkins, George Hodson, and Tralyn Hodson envision Flying Fox as a project-based winery with room for creative exploration in the winemaking process. Many locals may recognize the Hodson family name, as they’re the winemaking team behind…

Veritas Vineyard & Winery

Located 12 minutes from Chiswell

The Hodsons have deep roots in the Virginia wine community. Andrew and Patricia Hodson started Veritas in 1999. Twenty years later, the large operation now involves multiple generations of the family.

Located in Afton, Veritas boasts incredible views of the Blue Ridge Mountains and acres of grapevines. Whether you prefer to soak up the sun on the lawn or grab an indoor table, there’s space for groups of all sizes.

This winery is a must-visit for followers of Virginia LOVEworks. In Veritas’ indoor tasting room, there’s a LOVEwork displayed just above the wine bar, crafted from hundreds of wine corks. Visitors can admire the sign while ordering from the winery’s extensive menu. Snapping a keepsake photo makes for a beautiful memory of time well spent.

Veritas tasting room

While it’s true that the best wineries on the Monticello Wine Trail often boast awards (and yes, we have our fair share), what really sets them apart, in our opinion, is the warm welcome you get from a family-run venue. This is especially true for those with involvement from multiple generations; the more branches on the family tree, the better!

We hope you enjoy visiting these and other must-try Crozet wineries during your explorations through Virginia Wine Country. Next time you visit our Big Ash Bar, let us know what you think on Facebook or Instagram!