What if your next Virginia road trip came with mountain waterfalls, vineyard tastings, scenic drives, and some seriously good views between every stop?
This route pairs locally made wine with waterfall hikes, taking you from rows of grapevines to forest trails where cascades tumble over massive rock ledges.
Along the way, you’ll tackle hikes ranging from quick walks to longer climbs, sample some of Virginia’s best-known wines, and find plenty of places worth pulling over for.
Keep reading for the full Virginia wineries and waterfalls road trip, including what to do at each stop and the details you’ll want before hitting the road.
1. Stone Tower Winery, Leesburg
Stone Tower Winery sits on a more than 400-acre estate just 15 minutes from Leesburg, about an hour from Washington, D.C., with rolling vineyards and wide views of the Blue Ridge foothills.
The family-owned winery grows grapes on the property and is best known for estate wines, including Chardonnay, Cabernet Franc, and Bordeaux-style red blends.
Stop by the Harvest Barn Tasting Room to enjoy a guided five-wine tasting, order wine by the glass or bottle, and grab food while looking across rows of grapevines and Loudoun County farmland.
The winery also offers vineyard tours, outdoor seating, seasonal events, and several tasting spaces, making it an easy road-trip stop before heading toward Northern Virginia’s waterfall trails and mountain hikes.
2. Dark Hollow Falls, Shenandoah National Park
It’s time for some rushing water at Dark Hollow Falls, located near mile 50.7 on Skyline Drive in Shenandoah National Park.
The 70-foot waterfall tumbles over several rocky ledges, and you can reach it on the 1.4-mile round-trip Dark Hollow Falls Trail, which drops about 440 feet from the trailhead.
The hike is short but steep, so save some energy for the uphill climb back after snapping photos beside the cool, shady cascades.
Dark Hollow Falls is one of Shenandoah’s most popular waterfalls, and its trailhead sits near Big Meadows, where you might spot white-tailed deer.
3. Early Mountain Vineyards, Madison
Next, head toward Madison and reward those tired legs with a glass at Early Mountain Vineyards, about a 50-minute drive from Shenandoah National Park.
This 350-acre property near the Blue Ridge Mountains grows grapes including Cabernet Franc, Petit Manseng, Chardonnay, and Merlot, with several wines made from its own estate fruit.
Inside the tasting room, grab a rotating wine flight and pair it with dishes featuring ingredients from Virginia farms, or relax in the Meadow overlooking the property.
Early Mountain also pours select bottles from other Virginia producers, so you can sample more of the state’s wine scene without adding another winery to your road trip.
4. Veritas Vineyards & Winery, Afton
From Early Mountain, drive about 1 hour to Afton, where Veritas Vineyards & Winery sits at the base of the Blue Ridge Mountains, just a few miles from the Blue Ridge Parkway.
The Hodson family founded Veritas in 1999, and today the winery produces bottles from grapes including Viognier, Cabernet Franc, and Petit Verdot.
Order a tasting or glass inside Veritas’s tasting room, then head outside to the lawn for vineyard views with the mountains rising behind the vines.
Veritas is also known for its summer Starry Nights concerts, when live music fills the property, making this stop a fun change of pace before you chase down the next Virginia waterfall.
5. Crabtree Falls, Tyro
After relaxing with a glass at Veritas, head about 45 minutes toward Tyro for Crabtree Falls, a huge series of cascades crashing down the slopes of George Washington National Forest.
The falls drop roughly 1,200 feet in total, with one section plunging about 500 feet, earning Crabtree a reputation as one of the tallest cascading waterfalls east of the Mississippi River.
Follow the 3-mile round-trip Crabtree Falls Trail, which passes several overlooks where you can watch water rush over massive rock faces.
The first viewpoint is only a few hundred feet from the parking area, but hiking higher brings even bigger views.
6. Apple Orchard Falls, near Sedalia
Keep the hiking shoes handy after Crabtree Falls because Apple Orchard Falls is about 1 hour and 40 minutes away near Sedalia, where a 200-foot waterfall spills down a tall rock face in Jefferson National Forest.
The most popular route starts at the Sunset Field Overlook around milepost 78.4 and follows the Apple Orchard Falls Trail for about 1.2 miles one way.
You’ll follow North Creek through shady forest, cross wooden bridges, and tackle steep switchbacks before a wooden viewing platform puts you right below the rushing falls.
Spring brings especially strong water flow, while the climb toward the falls includes stairs and rocky sections that make this a major leg workout.
7. Chateau Morrisette Winery, Floyd
After the long trek to Apple Orchard Falls, give your hiking boots a break and drive about 2 hours to Chateau Morrisette Winery, located near Floyd at milepost 171.5.
The Morrisette family planted its first vines here in 1978 and produces a huge range of wines, from Cabernet Sauvignon and Chardonnay to sweet favorites like Our Dog Blue, a Riesling-Traminette blend featuring the winery’s famous dog-themed label.
Book a tasting to sample several pours, browse the gift shop, or settle in for lunch at the on-site restaurant while looking across the surrounding Blue Ridge Mountains.
Chateau Morrisette can produce up to 60,000 cases of wine each year, and its timber-framed winery building includes massive salvaged Douglas fir beams, giving you something impressive to check out between glasses.
8. Cascade Falls, Pembroke
Finish your Virginia wineries and waterfalls road trip by heading toward Pembroke, where Cascade Falls drops 66 feet into a rocky pool in Jefferson National Forest.
The popular Cascades National Recreation Trail runs about 4 miles round trip as it follows Little Stony Creek through the forest.
Take the Lower Trail for close-up views of rushing water, bridges, and small cascades before the main waterfall appears between towering rock walls at the turnaround point.
Pack sturdy shoes for the rocky path, bring a picnic for the recreation area, and enjoy one final waterfall before wrapping up a road trip packed with Virginia wine, mountain hikes, and plenty of miles well spent.
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