12 Scenic Drives Through Virginia Wine Country

There is a popular saying amongst winemakers: "Grapes don’t grow in ugly places." That is certainly true for Virginia vineyards — stunning landscapes through the mountains, foothills, and waterfront wineries will make anyone fall in love with the Commonwealth.

Take a drive* through scenic Virginia Wine Country and plan a few stops at vineyards along the way to explore why Virginia is for Wine Lovers.

*Remember to designate a driver.
 

JUMP TO TRAILS IN: Virginia Piedmont & Central Virginia | Shenandoah Valley | Northern Virginia | Virginia Mountains | Coastal Virginia
 

Virginia Piedmont & Central Virginia Wine Trails

The Monticello Wine Trail is one of the largest and most heralded wine regions in Virginia. Named the 2023 Wine Region of the Year by Wine Enthusiast, the area beat out other famed wine destinations like France’s Provence and Italy’s Lambrusco. Centered around the Charlottesville area, this trail of 40+ vineyards meanders through the foothills of the Blue Ridge Mountains, showcasing both unbeatable views and incredible wines. 

From its most eastern point, the Monticello Wine Trail easily leads into the Fermentation Farm Trail west of Richmond. This trail runs through the rolling hills and farmland of Central Virginia and includes four wineries, two cideries, and four breweries. Learn more about each stop along the way and what’s on tap before planning your ideal route through this scenic rural countryside.

An area lovingly referred to as the "sunrise side" of the Blue Ridge, Nelson County boasts the Nelson 151 Trail. The 151 stands for Route 151, a drive that includes seven wineries, five breweries, two cideries, and four distilleries. Trail Map

Notable Stops Along the Way

In addition to delicious wines, you’ll also find world-famous historical sites like Thomas Jefferson’s Monticello and James Madison’s Montpelier in this region. We’ve got a few more pit stops worth pausing your road trip:

• The Market at Grelen–A European-style garden shop and cafe with on-site walking trails and pick-your-own produce available seasonally. 
• Liberty Mills Farm–Pick fresh flowers or pumpkins, depending on the season, at this family-friendly farm. In the fall, don’t miss conquering the corn maze, the largest in the entire country! 

Where to Eat 

Between the Charlottesville area and Richmond, you’ll find an expansive culinary scene to satisfy even the most discerning foodie. Here are a few suggestions to add to your itinerary.

• Cou Cou Rachou–Delightful French bakery serving artisanal coffee, fresh pastries, breads, and other tasty treats. 
• Marigold at Keswick Hall–A restaurant by acclaimed Chef Jean-Georges; local, seasonal, and organic ingredients are always the focus of this critically acclaimed dining destination. 
• The Yellow Mug–Coffeehouse and pastry shop with a cozy vibe in the small mountain town of Crozet. 
• Blue Mountain Brewery–Family-friendly farm brewery located on Route 151 with indoor/outdoor dining options, fun yard games, and wide open views of the Blue Ridge Mountains. 
• Three Blacksmiths–Upscale dining in the quaint town of Sperryville that serves a fixed weekly dinner menu of local, seasonal foods.
• Smyrna–Nominated for a James Beard award in 2026, Smyrna specializes in Aegean-Mediterranean cuisine. 
• The Roosevelt–A James Beard-nominated restaurant in Richmond’s historic Church Hill neighborhood, known for its Southern flavors with a twist.  

Where to Stay

Central Virginia has endless lodging options that cater to every type of traveler, from large groups and families to luxury-loving couples. 

• Wintergreen Resort–A four-season family-friendly property right off the Blue Ridge Parkway that offers skiing, tubing, hiking, and other seasonal activities. In addition to the main lodge, Wintergreen has private cabins available for group bookings. 
• Lydia Mountain Lodge–Rustic mountaintop lodge and private cabins in Stanardsville with sweeping views of the Blue Ridge Mountains. 
• Blue Rock–A boutique luxury inn surrounded by 80 acres of rolling landscape in Rappahannock County. 
• Boars Head Resort–Luxury resort on the outskirts of Charlottesville. 
• The Draftsmen–Conveniently located in downtown Charlottesville, just blocks from the University of Virginia campus. 
• The Jefferson–Richmond’s most iconic upscale hotel. Don’t miss dining at Lemaire, the on-site restaurant. 
• Quirk Hotel–A must for modern art lovers looking for accommodations in the downtown Richmond area. During warmer months, the rooftop bar offers unparalleled views of the city skyline. 

Need more help planning your Central Virginia road trip route? Use these guides to Charlottesville and Richmond to round out your journey. 

Shenandoah Valley Wine Trails

No matter which road you travel through the Shenandoah Valley, you’ll most likely find yourself following one of the region’s wine trail routes. The larger trail, The Shenandoah Valley Wine Trail, includes 21 wineries, two meaderies, and a brewery between Berryville and Eagle Rock—a distance of 177 miles. You’ll surely need several days to visit even a fraction of the wineries and enjoy the famous scenery of the Shenandoah Valley while exploring this wine trail.

The Blue Ridge Whiskey Wine Loop runs from Front Royal on Route 522 to Warrenton, across Route 211 to Sperryville, and continues on Route 34o through Luray to Front Royal again. With eight wineries, four distilleries, and four breweries, you might opt to stretch your journey out over two or three days. Trail Map

Notable Stops Along the Way

• Luray Caverns–Largest cavern system in the eastern U.S., made famous by its “Stalagpipe organ,” which plays music using the natural calcified formations of the caverns. 
• Shenandoah National Park–One of the most iconic National Parks in America. Follow Skyline Drive for a leisurely route through the beautiful Blue Ridge Mountains. 
• Natural Bridge State Park–200-foot-tall limestone bridge carved out of the landscape over centuries by the creek that runs through it. 
• Blue Ridge Parkway–469-mile route that runs through the Blue Ridge Mountains of Virginia, with dozens of scenic pull-offs where travelers can take in the natural beauty of the mountains. 

Where to Eat 

The Shenandoah Valley is an expansive area with dozens of popular restaurants, so you’ll have plenty of delicious options to choose from.

• Bella Luna Wood-Fired Pizza–Harrisonburg hot spot for handmade pizzas and pastas.
• Zynodoa Restaurant–Upscale eatery in Staunton serving farm-to-table fare made with locally sourced ingredients. 
• Woodstock Cafe–Small-town cafe known for fresh fare, including an array of delicious sandwiches. Peruse the on-site wine and craft beer shop, stocked with local products.
• Porch+Vine–Luray restaurant with a from-scratch Contemporary American menu. 

Where to Stay

• Shenandoah Yurt–One-of-a-kind yurt featuring sumptuous accommodations, a full kitchen, a hot tub that looks out on the mountains, and all sorts of family-friendly amenities, from an archery range and bike rentals to a pool table and an outdoor grilling and campfire space. 
• The Historic Inn at Oakdene–Stunningly renovated historic property just blocks from Staunton’s charming downtown. 
• Mimslyn Inn–Historic hotel in downtown Luray, just a few minutes from Luray Caverns and Shenandoah National Park. 
• Massanutten Resort–Four-season resort near the Swift Run Gap entrance to Shenandoah National Park. On-site activities include skiing, mountain biking, hiking, ziplining, a treetops ropes course, and an indoor/outdoor water park. 

Want to focus more on the scenery rather than the wine? We’ve got five awe-inspiring road trips through the Shenandoah Valley that showcase the famed beauty of the area. 
 

Northern Virginia Wine Trails

With more than 50 wineries in this acclaimed wine region, Northern Virginia can feel a little intimidating. What better way to create an approachable itinerary than to think of a gigantic wine trail than in clusters? 

Branch off on one or two of the Loudoun: DC's Wine Country clusters for a delicious couples weekend away. Each cluster is six to eight wineries strong and includes destination dining hot spots as well. 

South of the Loudoun trails is the Fauquier County Wine Trail, featuring 24 wineries. This trail spreads from Delaplane off Route 17 to Sumerduck off Route 29. Route 55 is the main east-to-west corridor of this trail. 

Picking up in Warrenton, the Skyline Tasting Trail follows Route 211 to "Little" Washington and has six wineries as well as a bevy of breweries, cideries, distilleries, restaurants, and more. Along the way, you can choose to stop and sip at a few of the wineries, or continue past Washington to Luray and on up the mountain to pick up Skyline Drive through Shenandoah National Park.

Notable Stops Along the Way

• Steven F. Udvar-Hazy Center–Smithsonian museum housed in two large hangars filled with over 3,000 history-making objects, including over 200 aircraft and spacecraft.
• Antique Shops in Middleburg–Middleburg is well known as a destination for antique lovers, and travelers often come from all across the eastern seaboard to select pieces from the numerous antique shops in downtown Middleburg. 
• Wagyu Beef Tours at Ovoka Farm–Custom farm tours complete with a ride to the top of Paris Mountain. After touring the cattle pastures and learning about the ethical and humane efforts that go into producing high-quality wagyu beef, stop by their store to take home a few pounds of your favorite beef cuts.
• Sky Meadows State Park–Northern Virginia state park designated as an International Dark Sky Park and boasts beautiful vistas, access to the Appalachian Trail, and horseback riding trails.

Where to Eat 

• The Conche–Creative restaurant that is a must for chocoholics. Within the restaurant, guests can watch the pastry team craft beautiful, flavorful chocolates and chocolate desserts. 
• Claire’s at the Depot–Contemporary American cuisine in a restored turn-of-the-century train station. 
• Field & Main Restaurant–Hearth-inspired, locally sourced, and globally-inspired cuisine in the small town of Marshall.
• The Red Truck Bakery–Beloved bakery with two Northern Virginia locations–Marshall and Warrenton. 
• The Ashby Inn & Restaurant–Bed & breakfast in the tranquil village of Paris, Virginia, with a fantastic restaurant serving dishes made with ingredients harvested from the on-site garden. 

Where to Stay

• Lansdowne Resort–Leesburg resort that offers extensive golf and wellness amenities for visitors, including 45 holes of golf and an on-site spa center. 
• Airlie–Historic resort on 300 acres of pristine gardens and wooded lands that are reminiscent of an English estate. 
• The Red Fox Inn & Tavern–Historic lodging in the heart of Middleburg, dubbed the "Nation's Horse & Hunt Capital,” and surrounded by a handful of notable wineries. 
• The Inn at Little Washington–Opulent inn known for its over-the-top decor and its two Michelin-starred restaurant. This is the place to stay for memorable getaways and romantic retreats. 

This itinerary covers just a small section of Northern Virginia, so be sure to check out the full list of suggested activities, restaurants, and places to stay for a road trip through Northern Virginia. 
 

Virginia Mountains Wine Trails

Along the Bottled in Bedford Craft Beverage Trail, aficionados will experience the tastes of five vineyards and wineries from the Blue Ridge Parkway to Smith Mountain Lake. If you’re looking for other beverage options, Apocalypse Ale Works offers craft beers, while Graham Ordinary Meadery serves meads and even allows visitors to book overnight accommodations at the rustic mountain lodge—a stay that includes picturesque mountain views from the rooms. 

Notable Stops Along the Way

• Thomas Jefferson’s Poplar Forest–National Historic Landmark that was designed by Thomas Jefferson as his secluded retreat. 
• National D-Day Memorial–U.S. memorial to World War II and the heroes of D-Day. 
• Boating or Fishing at Smith Mountain Lake–Large reservoir with more than 500 miles of coastline that offers fishing, boating, swimming, and other water sports opportunities. 
• Peaks of Otter Hikes–Hiking trails of varying difficulties along the Peaks of Otter mountains. Three most popular trails are Sharp Top Trail, Harkening Hill Loop Trail, and Flat Top Trail.

More Virginia Mountain Wine Trails to Explore

• The Wine Trail of Botetourt

Where to Eat 

• Town Kitchen Provisions–Stocked with an array of baked goods, handcrafted sandwiches, and a selection of home-cooked meals to eat in or take away. 
• Sourdough Pizza Company–Wood-fired, brick-oven pizza. 
• Bräuburgers–Hamburgers and craft beer in the small town of Forest. Don’t miss asking about the history of Ernst, the Dachshund pup that inspired the establishment. 
• Blue Ridge BBQ–Award-winning barbecue spot in Forest. 

Where to Stay

• Peaks of Otter Lodge–Lakefront lodge that sits along the Blue Ridge Parkway, surrounded by the majestic Peaks of Otter.
• Bedford Landings Bed & Breakfast–Smith Mountain Lake bed and breakfast that welcomes visitors arriving by car, boat, or even by plane, as the owners can accommodate pilots landing at Bedford Landings. 
• Mariner’s Landing Resort & Conference Center–1,000-acre community on Smith Mountain Lake. Amenities include a golf course, indoor and outdoor pools, beach area, fitness center, and on-site restaurants. 

With Roanoke just a short drive away from the Bottled in Bedford Craft Beverage Trail, there are endless options for dining, lodging, and fun-filled pit stops. 
 

Coastal Virginia Wine Trails

The Chesapeake Bay Wine Trail contains six wineries and one cidery, all located on the Northern Neck peninsula. The coastal scenery of the Chesapeake Bay and its converging waterways creates a tranquil backdrop for the wineries located in this far-east region of the Commonwealth.

 Notable Stops Along the Way

• Westmoreland State Park–State park overlooking the Potomac River with hiking trails and a beach where visitors enjoy sifting through the sands looking for the abundant supply of shark teeth that are known to wash up on the shores. 
• Stratford Hall–Historic estate of the Lee family on the Potomac River that spans nearly 2,000 acres and offers on-site lodging options for couples, families, and groups.
• Menokin–Historic ruin of the home of Francis Lightfoot Lee, a signer of the Declaration of Independence. Missing sections of the home have been rebuilt with architectural glass, which visually shows the process of reconstruction.
• Steamboat Era Museum–Learn about the romanticized steamboat era of America through the museum’s collection of artifacts and exhibits, including a preserved steamboat. 

Where to Eat 

• Circa 1892–Gourmet cheese and wine shop with a menu featuring an array of specialty sandwiches, salads, and small bites. 
• Adrift–Fine dining eatery serving classic coastal dishes and cocktails, plus wine.
• Car Wash Cafe–Classic diner in a renovated car wash. 
• Merroir–Rappahannock Oyster Company’s waterfront restaurant, serving their own fresh oysters pulled straight from the waters you dine beside.  
• Salt & Meadow–Upscale on-site restaurant at the Tides Inn that sources seafood and meats from local watermen and farmers. 

Where to Stay

• Riverview Inn–Restored 1950’s inn that has been transformed into modern waterside accommodations. 
• The Tides Inn–Waterfront luxury inn that focuses on sustainability and the conservation of Virginia’s waterways, including the oysters of the Chesapeake Bay. 
• Hope & Glory Inn–Restored schoolhouse with an on-site micro-vineyard and upscale dining room. 
• Harmony Tides Cottage–Gingerbread-style house overlooking Carter’s Creek in Irvington that is perfect for family getaways to the Chesapeake Bay. 

Virginia’s Northern Neck is a massive peninsula with many worthwhile stops along the way. Use our full road trip guide to the Northern Neck for your planning.
 

While these trails are a great starting point for those looking to discover Virginia’s award-winning wine scene, they do not include every winery in Virginia. See our directory of more than 300 wineries and vineyards to see all that Virginia has to offer for lovers of wine.