Scenic Hikes near Virginia Wineries

Talk about a pairing. When you combine visiting a Virginia winery with a hike in Virginia’s bountiful natural glory, the sensory delights extend far beyond the palette! Furthermore, touring a winery can be a scenic experience in its own right – viewing the rows of grape arbors, walking wonderfully landscaped grounds on cobblestone paths and soaking in views of the rolling countryside. And let’s not forget the tastings, whether they are indoors or out. 

However, just because we love wine tastings and touring wineries doesn’t mean we can’t add a walk or hike to the adventure. Hiking to a nearby waterfall, overlook or historic site just might build up an appreciation for the great outdoors and perhaps a thirst for the harvest.

Here are some Virginia hikes paired with nearby wineries. 

Danville Riverwalk

The Winery: 2 Witches Winery & Brewery

Nearest Town: Danville

The Pairing: The 2 Witches tasting room is generally open in the evenings, giving you the afternoon to get in your hike. An immediate choice is the Danville Riverwalk Trail. This 9-mile greenway travels along the north bank of the Dan River and has been incorporated into the existing infrastructure. On its journey, the Riverwalk passes through hub parks such as Dan Daniel Memorial Park and Anglers Park. The trail is paved and is popular with joggers, bicyclers and walkers. Along the way, it tells the story of Danville from its industrial and Civil War past to today, where we see natural beauty integrated into this linear trail system.

If you are looking for something a little more rustic, try Fairy Stone State Park, about an hour’s drive west. Explore Stuarts Knob and early 1700 mining industry. Follow Civilian Conservation Corps built trails, all encapsulated in hilly wooded terrain enhanced with natural beauty, including a cleared view from the shoulder of Stuarts Knob.

Find more things to do with our complete guide to visiting Danville. 

Dutch Gap Loop

The Winery: Upper Shirley Vineyards 

Nearest Town: Hopewell

The Pairing: This winery is run by native Virginians who returned home after careers elsewhere. Love of home led them to a historic house and farm to cultivate their passion for winemaking. 

Just a few miles to the west lays the equally historic Henricus Historical Park, where you can hike in preserved wildland near the famous recreated Henricus Village of the 1600s. Long ago, English colonists settled in the area, forming Henricus, a community around which a defensive ditch was built. The moat became known as the Dutch Gap. Fast forward, as commercial traffic increased on the James River, a canal was cut across a loop in the James, forming a big oxbow lake. Now Dutch Gap is preserved and you can make a 4.7-loop hike amid these wetlands starting behind the Henricus Village visitor center.

Split Rock from Harpers Ferry

The Winery: 868 Estate Vineyards 

Nearest Town: Purcellville

The Pairing: This northern Virginia winery combines the old and the new in producing their vino. In addition to tastings, visitors can enjoy music at times and a restaurant using locally sourced cuisine. 

Add a little more nature by making the 6-mile there-and-back hike to Split Rock. Pick up the Appalachian Trail in nearby Harpers Ferry, West Virginia (the only place with good parking for this hike). Cross the Shenandoah River, pass a homesite then climb to the state line dividing West Virginia and Virginia. Follow the Virginia boundary to Split Rock, where a fantastic view opens down the Potomac River dividing Maryland and Virginia and upriver to Harpers Ferry.

Appalachian Trail on Brown Mountain Creek

The Winery: Ankida Ridge Vineyards

Nearest Town: Amherst

The Pairing: This high country winery is perched on the east slope of the Blue Ridge, nestled in at 1,800 feet. Now known as Virginia’s “Little Burgundy,” the winery strives to be as organic as possible, even down to using sheep to graze the vineyard floor.

The Appalachian Trail is within easy striking distance, just a few miles away. Leave US 60 at Long Mountain Wayside and head south. Take a 4.6-mile there-and-back hike into Appalachian Mountain history, visiting a formerly inhabited hollow along Brown Mountain Creek. Here, a gorgeous wooded valley is centered by a raucous stream, once populated with scores of sharecroppers. While hiking look for evidence of these former residents, whether it is old stone fences, stone spring boxes, even a chimney, all fading into the past, as the forest grows ever tall and lush.

Sky Meadows State Park

The Winery: Arterra Wines

Nearest Town: Delaplane

The Pairing: Arterra Wines is managed by a husband-wife team who incorporate art and culture into their bold fruit wines. They fully embrace the Virginia winery culture. 

Sky Meadows State Park is just a few miles distant from Arterra. Immerse in the countryside where Arterra stands while hiking here. This 5-mile loop hike starts near the ranger station. Take the Piedmont Overlook Trail and enjoys two vistas, then joins the Ambassador Whitehouse Trail, reaching another overlook. Finally, pick up the Appalachian Trail and tread that famous path south for a couple of miles before looping back to the trailhead via the North Ridge Trail.

Savage Neck Dunes Natural Area Preserve

The Winery: Chatham Vineyards 

Nearest Town: Eastville

The Pairing: Operated by a second generation Virginia winery family on a centuries old working farm, the proprietors feature 20 acres of high density, high quality European-style vines. Their grapes are handpicked and assorted to ensure high quality wines.  

A few miles south of Chatham Vineyards stands Savage Neck Dunes Natural Area Preserve, a protected Virginia resource. The preserve is best known for sand dunes rising 50 feet high from Chesapeake Bay. The preserve safeguards a mile of wild shoreline abutting Chesapeake Bay,where views will enhance your walk. Visitors accessing the preserve can trace a ¾-mile trail through the dunes to the beach, where you can enjoy walking the sandy shoreline.