Fall in Virginia offers many fun activity combinations, but one of our favorites is hiking and wine. October is Virginia Wine Month, which makes it the perfect time to sample fine vintages during the grape harvest and also experience the colorful canopies shading some of our favorite hiking trails. 

In Virginia’s Blue Ridge, we have a number of wineries that are close to great hiking trails, and we’ve done the research for you identify the best matches. Grab a partner, put on your sturdy shoes, and set off for a day of spectacular views and tasty wine.

Hoop Hole | Virginia Mountain Vineyards

In Eagle Rock is Hoop Hole, a figure-eight trail nearly 10 miles long near Roaring Run Recreation Area. The upper and lower loops are popular with mountain bikers, but hikers love it, too. Virginia Mountain Vineyards is less than 30 minutes away in Fincastle, and their views are among our favorite. The tasting room will be closed September 24 through October 24, except for scheduled weekend events

Roaring Run | Blue Ridge Vineyard

Blue Ridge Vineyard - Botetourt County, VA

One of the most popular trails in Virginia’s Blue Ridge is Roaring Run Trail through the Roaring Run Recreation Area in Eagle Rock. The Roaring Run Furnace and a series of cascading waterfalls are the draw. About 20 minutes away is Blue Ridge Vineyard. Their sweeping views include fields and mountains, which will surely put on a show this season. Sundays are for live music and wine, so plan your hike for the morning.

PRO TIP – Roaring Run and Hoop Hole as well as Blue Ridge Vineyard and Virginia Mountain Vineyards are all close to each other and can be interchanged for a different experience.

>> Best Hiking Trails to Bring Your Dog

Smith Mountain Lake State Park | Hickory Hill Vineyards & Winery

Choose from 13 hiking trails at Smith Mountain Lake State Park. Some offer views of the sparkling water while others take advantage of the foliage and remaining shade of the woods. In about 10 minutes you can be from the park to Hickory Hill Vineyards & Winery in Moneta. Heads up! Sundays in October are for Cabs by the Campfire. Bring a blanket or chair to be comfortable while you sip.

Bottom Creek Gorge | AmRhein’s Wine Cellars

Virginia’s second highest waterfall (200 feet) is accessible by the Bottom Creek Gorge Trail on Bent Mountain. Linger a while and definitely bring a camera to capture this beautiful slice of nature. Less than three miles away is AmRhein’s Wine Cellars and their award-winning German-inspired wines. 

Peaks of Otter | Peaks of Otter Winery & Orchards

Sharp Top Mountain - Blue Ridge Parkway

The three peaks of Peaks of Otter are among the most notable in Virginia’s Blue Ridge. From Sharp Top you can see for miles, and it’s the most accessible of the three with a shuttle to the top for those who are less able to hike. Whichever trail you choose, follow it up with a visit to Peaks of Otter Winery and Johnson’s Orchard less than 20 minutes away. Facing opposite the Peaks of Otter, the farm winery is a great place to look back at the foliage you just enjoyed.

>> 10 Easy Hiking Trails on the Blue Ridge Parkway

Rocky Knob Recreation Area | Chateau Morrisette

Four trails are available at Rocky Knob Recreation Area on the Blue Ridge Parkway. Smart View Trail is an easy, popular trail, as it’s a mostly level 2.6-mile loop. However, the Rock Castle Gorge Trail is the cream of the crop for true hiking enthusiasts. At nearly 11 miles in length, the trail dishes out more than 1,800 feet of elevation change. It’s considered moderate to strenuous. It will certainly make you earn that excellent glass of “Our Dog Blue” waiting for you at Chateau Morrisette, an award winning winery located at Milepost 171.5 on the Parkway. In addition to beautiful views and delicious wine, you can also take part in winery tours and dine in the Chateau Morrisette Restaurant.

Claytor Lake State Park | Whitebarrel Winery

Stroll along four miles of easy trails at Claytor Lake State Park this fall. We like the Lakeview Trail. At just under a mile long, it runs alongside Claytor Lake and will offer a breathtaking view of the foliage reflecting off the water. 20 minutes away at Whitebarrel Winery there is a glass of plum wine waiting for you. It’s a refreshing white infused with plums and a perfect post-hike delight.

>> 10 Hikes for the Best Fall Colors

Poor Mountain | Valhalla Vineyards

Valhalla Vineyard - Roanoke, Virginia

The Poor Mountain Trail in the Poor Mountain Natural Reserve is a moderate 3.4-mile loop with switchbacks and nice views when the leaves begin to fall from the trees. Allow two to three hours for the hike, then rest with the 20-minute drive to Valhalla Vineyards. Their wines are French but their view is 100% Virginia’s Blue Ridge. Soak it all and don’t miss seeing their wine cave!

Dragon’s Tooth | Beliveau Estate Winery

As part of the Virginia Triple Crown along the Appalachian Trail, Dragon’s Tooth is one of the most iconic hikes in Virginia’s Blue Ridge. It’s a challenging trek that puts your climbing and bouldering skills to the test, but you’ll be amazed at the 35-foot tall quartzite rock that points toward the sky as the “tooth.” Get a taste of the truly wild and then make a beeline for Beliveau Estate Winery. Their acreage is less wild and their wine feels like a personal award. Tip back a glass of Trailblazer Merlot, you trailblazer, you.

>> 10 Great Hiking Trails in Virginia's Blue Ridge

Booker T. Washington National Monument | Brooks Mill Winery

Managed by the National Park Service, Booker T. Washington National Monument interprets the birthplace of a boy born into slavery who became one of the great educators of his time. Explore the park by way of the two main trails – Plantation Trail and Jack-O-Lantern Branch Heritage Trail. You’ll encounter the historic sites of the Burroughs family home, the Booker T. Washington birthplace, the reconstructed kitchen cabin, the tobacco barn, and two cemeteries.

Five miles away is Brooks Mill Winery, a small, family-owned winery that’s perfect for unwinding. Their fruit wines are a delight. We especially enjoy the Sangria.


Map of Locations


Virginia's Blue Ridge Cheers TrailVirginia’s Blue Ridge Cheers Trail

The wineries in the region are part of the Virginia’s Blue Ridge Cheers Trail! Before you go, register for our Cheers Trail Passport Program and then check-in at each location you visit for exclusive special offers. Once you check in at five spots, we’ll send you a free Cheers Trail t-shirt! Learn more >


Show us what you’re sippin’ and how you’re hikin’. Chronicle your adventures on Instagram and tag #BlueRidgeDay and #VBRCheers. Keep an eye on the foliage and fun things to experience this fall by receiving our enewsletter. Subscribe >

Header photo of Sharp Top Mountain courtesy of Sarah Hauser - Virginia Tourism Corporation