Fall is officially here in Charlottesville and Albemarle County, and there's no better place to experience the changing landscape than along the Monticello Wine Trail.
Whether you're looking for a cozy winery to spend a quiet afternoon or a more expansive space with mountain views, there is truly something for everyone. Blankets, firepits, and seasonal snacks abound throughout the area, so take your pick! Here are five wineries to get you started, recommended by Tasha Durrett, founder of Black Women Who Wine.
Just a 15-minute drive from downtown Charlottesville, Southwest Mountains Vineyards sits in the foothills of the Southwest Mountain Range in Keswick. It's loved for its award-winning wine, full food menu, and homage to Virginia hunt country. Plus, its tasting room is picture-perfect, with cozy sofa seating areas and long, traditional tables.
At Southwest Mountains Vineyards, fall activities are abundant: check the winery's website to see what's coming up. If you’re looking for an elevated visit, book a ‘Hike and Wine’ experience on the winery's Glade Trail. The hike is two miles roundtrip and classified as intermediate, with a curated picnic and wine selection awaiting your arrival at the beautiful glade. Perfect for couples, friends, or solo adventurers looking for a unique blend of the outdoors and indulgence. Hikes must be booked in advance.
Jefferson Vineyards is beautiful any time of year, but a visit in the fall is especially memorable. Your experience starts with a scenic drive to the winery, perfect for taking in the colorful foliage. Once you arrive, settle in for a wine tasting either inside their cozy tasting room or outside surrounded by foliage. Thomas Jefferson’s influence on food and wine in Virginia is well documented and studied often, but a visit to Jefferson Vineyards offers a chance to experience that history firsthand. Best of all, Jefferson Vineyards is just 1.5 miles from Monticello, making it easy for you to visit both in the same day.
No matter the season, Afton Mountain Vineyards is a great choice for group outings, intimate dates, or solo wine tastings. Fall feels especially unique here, as the winery’s location is at the foot of the Blue Ridge Mountains and offers sweeping views of Virginia’s colorful fall foliage. Keep an eye on their calendar for fun events happening this fall – they’re the perfect add-on to any itinerary!
Located in Barboursville, The Barn at 678 Vineyard offers next-level hospitality, a relaxed atmosphere, and scenic views made even better by the thoughtful fall décor throughout the property. Come for a wine, beer, cider, or mead tasting and stay awhile for live music on most weekends. Seating is fun and varied, from indoor tasting room tables to multiple outdoor options. While you’re in Barboursville, take some time to explore the surrounding wineries, such as Barboursville Vineyards and Horton Vineyards.
Located just 10 minutes from downtown Charlottesville, Oakencroft Farm & Winery is an inviting spot to enjoy a fall wine tasting without venturing far from the city. Choose from wine flights, wines by the glass or bottle, and seasonal menu options that are thoughtfully crafted to complement the season. Enjoy your wine either inside their architecturally striking tasting room, outside on their covered patio, or lakeside surrounded by gorgeous fall foliage views.
These are just a few of the wineries worth experiencing along the Monticello Wine Trail this fall. Whether you’re traveling from across Virginia or coming from out of state, the trail is an easy reason to turn a wine-tasting day into a longer getaway in Charlottesville and Albemarle County. October is also Virginia Wine Month, making fall an especially great time to plan your visit and support Virginia wine. Add in colorful fall foliage, seasonal food and drink, and crisp days made for exploring, and you have all the makings of a memorable Virginia wine country getaway.
Tasha Durrett
Founder of Black Women Who Wine
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