Where Culture Meets the Vineyard: Experiencing Virginia Wine Month in Charlottesville

by Matt Harmon, Owner of Harmony Wine

October in Virginia is more than harvest season. It’s a celebration of community, creativity, and the evolving culture of wine in the heart of the Monticello Wine Trail.


Happy Virginia Wine Month! In recent years, Virginia’s wine scene has been gaining serious attention, and the Monticello region is leading the way. In 2023, it earned the title of Best Wine Region in the World, confirming what locals have known all along: this is a place where wine, culture, and creativity thrive together.

Across Charlottesville and Albemarle County, new projects are bringing a fresh energy to the wine community. From intimate tastings and curated dinners to events like Two Up, Wine Down and Daze of Rosé—both founded by people of color—the region’s wine story feels more inclusive and exciting than ever.

A man and a woman stand in front of grape vines each holding a glass of wine. The sun is setting behind them

October is a special time to explore Virginia wine country. It’s peak foliage season, and the Shenandoah region consistently ranks among the best places in the country to see fall color.

Spend a Sunday afternoon at King Family Vineyards, where the views stretch for miles and polo matches unfold just beyond the vines. Or take a drive through the rolling hills of Afton, stopping to sip at a few of the small, scenic wineries that dot the landscape. With the crisp air, golden light, and a glass of something local in hand, you’ll see why this is one of the best times of year to visit.

Close up of a man swirling wine in a wine glass

After the rush of harvest, many wineries settle into a slower pace. The crowds thin, and the focus shifts to cozy tasting room conversations and relaxed afternoons by the fire.

It’s the perfect time to meet the people behind the bottles and hear their stories. You might come across new names like Parallax, a Black-owned wine project redefining what Virginia wine can be. Whether you’re reconnecting with friends or trying something new, October invites everyone to slow down and savor what makes this community so special.

A man lounges on a patio chair with a glass of wine in hand

Picture this: sunlight spilling over rows of vines, soft R&B and Afrobeats in the background, and a group of friends laughing over glasses of red and rosé. The atmosphere is relaxed but stylish, rooted in connection and joy.

That’s what Virginia Wine Month feels like. From a Sunday at King Family Vineyards to an afternoon at Eastwood Farm and Winery, or a nightcap in downtown Charlottesville, this season brings out the best of what the region offers—good wine, good company, and a shared sense of ease.

A group of men reach out with their wine glasses to clink glasses together

Plan Your Visit

Virginia’s wine story continues to evolve, shaped by new voices, fresh ideas, and a commitment to community. As more Black and Brown winemakers and entrepreneurs join the scene, the experience becomes even more dynamic and welcoming.

If you’re looking for a fall getaway filled with warmth, connection, and incredible wine, Charlottesville is the place to be.

Start planning:

--Explore wineries along the Monticello Wine Trail

--Discover inclusive experiences with Discover Black Cville

--Attend local celebrations like Two Up, Wine Down

Author

Matt Harmon

Owner of Harmony Wine