Virginia wine country hits different, and nowhere is that more true than around Charlottesville. It’s all rolling vineyards, Blue Ridge Mountain views, and wine good enough to write home about. Whether you're a rosé-all-day person or a diehard red wine fan, these 10 wineries in Charlottesville promise to take you on a sip-by-sip adventure to remember.
Can’t decide where to sip first? We crunched the ratings from Yelp, TripAdvisor, and Google into one easy 10-point score. Think of it as your cheat sheet to Charlottesville’s best pours, though honestly, you can’t go wrong with any of them. Let’s count down from 12 to 1.
Address: 5022 Plank Rd, North Garden, VA 22959
Pippin Hill isn't just a winery it's a full culinary destination that also makes exceptional wine. The same husband-and-wife team behind Charleston's acclaimed Zero George created this spot, and their hospitality expertise shows in every detail, from the veranda strung with bistro lights to the thoughtfully crafted menu. The wine program is run by renowned winemaker Michael Shaps, featuring standout bottles such as their Viognier, Cabernet Franc, Chardonnay, and elegant red blends that showcase what Virginia terroir can do.
But here's what really sets Pippin Hill apart: Chef Tim Moore, who formerly worked at the legendary Inn at Little Washington, brings Michelin-level expertise to a menu that changes with the seasons. Think farm-to-table done right, with weekend brunch, wood-fired pizzas, seasonal small plates, and chef-inspired entrees that showcase Virginia's agricultural bounty. The food here is as much a draw as the wine, and reviewers consistently rave about both. Live music on weekends adds to the atmosphere, along with special wine dinners, yoga classes, and seasonal events you can find on their calendar .
Rated by reviews as "the most beautiful winery in Virginia," and gush about the stunning views and impeccable service. The food consistently gets top marks, many say it's the best meal they've had at any winery, and the elegant yet relaxed atmosphere makes it perfect for everything from romantic date nights to celebratory dinners. Some note that it's a bit isolated (about 20 minutes from other wineries) and on the pricier side, but most agree it's worth every penny for the complete experience.
Address: 6109 Wolftown-Hood Rd, Madison, VA 22727
Early Mountain made headlines in 2016 when it was named America's Best Tasting Room and one look at the soaring ceilings, floor-to-ceiling windows, and mountain views explains why. This isn't just a place to taste wine; it's a place to settle in for a full afternoon with a bottle and some seriously good food.
Their wine selection covers all the bases with Chardonnay, Pinot Gris, Syrah, Petit Verdot, and Cabernet Franc, offering something for every palate. Beyond regular tastings, Early Mountain hosts live music, seasonal vineyard dinners, and harvest celebrations check for their full event calendar.
Visitors consistently mention the "stunning" tasting room and "exceptional" food, calling it perfect for a leisurely weekend brunch followed by wine tasting. The service and hospitality get high marks across the board, with staff described as knowledgeable and welcoming. It's about 40 minutes north of Charlottesville (closer to Madison), so factor in the drive. Weekends can get busy, so reservations are advised.
Address: 234 Vineyard Ln, Afton, VA 22920
Plenty of wineries boast nice scenery, but Afton Mountain Vineyards has a view so good that you might forget Instagram exists. As one of Virginia’s OG vineyards (founded in ’78), it’s been blending stellar wines with mountain magic for decades.
Afton grows 11 kinds of grapes, which means plenty of ways to fill your glass, from crisp Albariño and floral Gewürztraminer to smooth, deep reds like Cabernet Franc and their award-winning Tradition blend (a Super Tuscan-style red that combines Merlot, Petit Verdot, and Cabernet Sauvignon). The Tannat is another standout, offering bold flavors that pair beautifully with grilled lamb or rich, savory dishes.
Stake out a spot in the pavilion, grab a picnic table, or sprawl on the grass with your snacks. Or go you can also try their Sip & Saddle horseback ride. Beyond casual tastings, Afton hosts their Afton After Hours music series one Saturday each month (with a food truck and $5 cover charge), plus private tastings and tours by reservation.
Praised the "absolutely gorgeous views" and "stunning" lake and vineyard setting, especially in the fall when the colors pop. The wines get consistent love, particularly the rosé and their red blends. Staff members are described as friendly and helpful, making the experience welcoming for both wine newbies and connoisseurs. A few reviewers note that the roads to get there are super windy (part of that Blue Ridge charm), and the tasting setup is self-guided with cards describing each wine rather than individual service. Most visitors say the views and quality wines make it well worth the scenic drive
Address: 240 Hazy Mountain Ln, Afton, VA 22920
Perched on the Blue Ridge ridgeline, Hazy Mountain Vineyards pairs wow-worthy scenery with grapes grown in two of Virginia’s best wine regions. Translation: the view’s incredible, and so is what’s in your glass.
The tasting room is equal parts airy and elegant, with open seating on the lawn, a breezy umbrella patio, and a covered terrace so you can stay cozy when the weather turns. You'll find everything from crisp whites to bold reds, plus craft beer for anyone who needs a break from the grape. Hungry? Order bites straight to your table, or time your visit for one of their themed dinners or live events they've even hosted a Taylor Swift–inspired 13-course meal, because why not? Check their event calendar to see what's coming up.
Address: 1353 Thomas Jefferson Pkwy, Charlottesville, VA 22902
Wine with a side of history? Yes, please. Just 10 minutes from downtown Charlottesville, Jefferson Vineyards sits on the same land where Thomas Jefferson first tried to grow grapes nearly 250 years ago.
These days, it’s all about easygoing vibes, with rolling hills, live music on the lawn, and a comfy tasting room. Their Viognier steals the spotlight (and plenty of awards), but you’ll also love the crisp Riesling, smooth Meritage reds, and a refreshing rosé that’s picnic-perfect.
Pair your flight with bites from The Vine food truck, find a sunny spot with a view, and toast to Virginia wine done right. If Jefferson could see this place now, he’d probably raise a glass right alongside you.
Address: 17655 Winery Rd, Barboursville, VA 22923
If Virginia wine country had a crown jewel, Barboursville Vineyards would be in the running. Founded in 1976 by Italian winemaker Gianni Zonin, the estate brought Thomas Jefferson’s long-ago dream of local viticulture to life and did it with serious style.
Here, you’ll find over 800 acres of history, along with a few surprises, including the Landmark Ruins of a 1800s Jefferson-designed mansion. Tastings range from casual Discovery Room flights to the elegant Library 1821, where you can sample older vintages alongside tasty seasonal goodies galore.
Barboursville’s star wine is Octagon, a rich Bordeaux-style red blend that’s earned plenty of awards, but you’ll also find refreshing whites like Viognier and Vermentino, plus Italian classics like Nebbiolo and Sangiovese. Yummers.
Address: 31 Blenheim Farm, Charlottesville, VA 22902
If you like your wine with a side of rock-star cred, you’re in luck because Blenheim Vineyards definitely delivers. (Oh yes, that Dave Matthews co-founded the place and even designs the labels for their collectible Painted Series.)
The vibe is ultra-relaxed, with a tasting room featuring glass floors that let you peek down at the wine production below. You can sip inside at the bar, grab a picnic table on the deck, or post up under the tent with a flight, glass, or bottle. Their Painted Red and Painted White blends are crowd-pleasers (and fun to collect), but you'll also find solid Albariño, Cabernet Franc, and more. Inside, they sell cheeses, charcuterie, and sandwiches from Simeon Market. On the first Saturday of each month (May through October), rotating food trucks roll in from 12-5 pm—past trucks have included Blue Ridge Pizza Co. and other local favorites. You're also welcome to bring your own picnic. Add occasional live music, and it's basically a mini wine festival for all to enjoy.
Guests love the ultra-relaxed atmosphere and the unique glass-floor tasting room that lets you watch wine production. The Painted Series wines are popular collectibles, and visitors appreciate the Dave Matthews connection without any pretension. The variety of seating options—from bar stools to picnic tables to tented areas makes it feel like a laid-back wine festival any day of the week.
Address: 330 Newtown Rd, Greenwood, VA 22943
Small but mighty, Pollak Vineyards has been working its magic since 2003, proof that good things really do come in boutique packages. With 34 acres of classic French grapes (hello, Viognier and Cabernet Franc), their wines lean elegant but stay refreshingly down-to-earth.
The tasting room and patio overlook a pond, rows of vines, and the Blue Ridge Mountains. They sell baguettes, cheeses, and meats in the tasting room, or you're welcome to bring your own picnic. Want peak vineyard vibes? Swing by for Final Fridays—the last Friday of every month from April through September—where live music from local bands (think bluegrass, jazz, acoustic roots), food trucks (Crozet Seafood Supply with lobster rolls and crab cake sliders, Cousins Maine Lobster, Thrill of the Grill), and sunsets team up for the perfect evening from 5:30-8:30 pm. Wine club members can reserve tables; everyone else is first-come, first-served, so bring blankets and lawn chairs.
Visitors consistently mention the peaceful setting and gorgeous views over the pond and mountains. The intimate, boutique feel sets Pollak apart from larger operations, and visitors love the combination of elegant wines and down-to-earth hospitality. The Final Friday events are singled out as must-attend gatherings that capture the best of Virginia wine country.
Address: 1575 Keswick Winery Dr, Keswick, VA 22947
Keswick Vineyards knows how to keep things classy without compromising on fun. They’ve been winning big since 2002 (including a pair of Governor’s Cups), but don’t expect any snobbery, just great pours, good conversation, and plenty of reasons to linger long after your tasting’s done.
You're always welcome to sip your way through award-winning wines like their standout Viognier in their laid-back courtyard. Come on Wednesdays for late-night tastings (open until 8:30pm) with live music on the first Wednesday of each month—it's become the midweek highlight for locals and visitors who want to turn hump day into something special. Be sure to stop by their Barrel & Board kitchen for snacks to keep you sipping—think shareables and small plates that pair perfectly with their wines. Last but not least, there's mini golf. It's not your typical vineyard perk, but sinking a putt between glasses of Viognier feels like a true wine-country flex.
Their guests love the relaxed atmosphere that balances quality with accessibility. The mini golf addition is frequently mentioned as a fun, unexpected touch, and the Wednesday music nights are called a highlight. The Barrel & Board food and award-winning wines keep people coming back, and the lack of pretension makes it welcoming for everyone from wine newbies to serious enthusiasts.
Address: 6550 Roseland Farm, Crozet, VA 22932
Want to see what Virginia wine is all about? Head to King Family Vineyards in Crozet, about 15 minutes from Charlottesville. This family-run winery has been crushing it since 1998, and the Blue Ridge Mountain views alone are worth the trip. But the Sunday polo matches from Memorial Day through mid-October definitely add an extra dose of charm you won't find anywhere else.
No need to stress about reservations or what to wear, either. Just roll up and start sipping. You get to pick whether you want to explore on your own or have their team guide you through the tasting. Either way, don't miss their Meritage red or the Rosé rosé. They sell gourmet cheeses, salamis, spreads, and hot French bread in the tasting room, but you're welcome to bring your own picnic—the covered veranda, expansive lawn, and brick patio are perfect for spreading out. Dogs? Kids? Picnic basket? Bring 'em all, then post up on the lawn or at a patio table for a full day of fun.
Wine Wednesday extends hours until 8:30 pm, with live music on the first Wednesday of each month. Food trucks roll through regularly—lobster rolls and crab cake sliders from Crozet Seafood, plus other local vendors serving everything from tacos to barbecue. Saturdays and Sundays at 11 am, 1 pm, and 3pm, you can book their Vineyard & Winery Tour for $50 per person—it includes a glass of Brut on arrival, a walk through the vineyards and barrel room, plus a Classic Tasting afterward.
Address: 3247 Carters Mountain Rd, Charlottesville, VA 22902
Tucked into Carter’s Mountain, Gabriele Rausse Winery feels like a secret garden for grown-ups who like their wine with a side of fresh mountain air. The tastings are outdoors, shaded by trees, with no frills. It’s just you, the view, and some seriously crush-worthy wines like Grüner Veltliner and Rosato.
Score a spot at their Set of Six release party, and you’ll feel like part of an inner circle. Not only do you get dibs on the freshest seasonal wines, but you also get to meet the makers, hear the stories behind each bottle, and sip along while getting a peek into the cellar secrets. These release parties happen throughout the year and they're the kind of intimate gatherings that turn casual wine drinkers into genuine enthusiasts.
Their reviews love the feeling of discovering something special off the beaten path. The outdoor, tree-shaded tastings create an intimate atmosphere that's worlds away from bigger, more commercial operations. Visitors consistently mention the quality of the wines—especially the Grüner Veltliner and Rosato—and the team's genuine, knowledgeable approach. The Set of Six events gets special praise for making guests feel like VIPs rather than just another tasting appointment.
Address: 2531 Scottsville Rd, Charlottesville, VA 22902
Just a winery? Not a chance. Eastwood Farm and Winery is the best winery on this list and your new favorite hangout disguised as a vineyard. Five minutes from downtown Charlottesville, this women-owned gem is where mountain views, raspberry vines, and wine slushies team up to ruin any chance of “just staying for an hour.”
Sip a gold-medal Rosé on the veranda while live music drifts in from the barn, or dive into baked brie so good it might deserve its own trophy. They run a seasonal farm-to-table menu with flatbreads, chocolate fondue, charcuterie boards, and shareables that pair perfectly with their award-winning wines. The Barn tasting room serves the full menu, while the Eastwood Grill food truck at the Tent delivers grilled chicken skewers, shrimp skewers, salads, sandwiches, and fries.
Wine Wednesday means 10% off bottles. Thursday Night Music Series brings live bands from 5:00-8:00 pm with $5 taps on beer and cider. Fridays kick off with the Low Country Shrimp Boil and live music. Saturdays deliver afternoon live music from 12:30-3:30pm, then Eastwood After Dark turns the barn into a party from 5-8pm. Sundays mix in Paint & Sip sessions, Music Bingo, and Maker's Markets. Between oyster feasts, sunset dance parties, and club-member exclusives, Eastwood brings the weekend energy every day. Come for the wine, stay because you can’t resist the vibe.
Sure, you could head out after the last sip. But why rush back home when all the best wineries are calling for an encore? Instead, do yourself a favor and kick back at one of Stay Charlottesville’s charming rentals. After all, the only thing better than Virginia wine country by day is a cozy spot to toast it all by night.
