Why Virginia’s the Place to Blaze a Trail This Fall

Aug 19, 2021

Pick your pleasure—say, hiking or wine tasting or horseback riding or good, old-fashioned country driving—and it’s got its own trail, if not several, in Virginia. And fall is arguably the best time to see for yourself.

For starters, the state’s legendary foliage gives new meaning to trail-blazing. And beyond those near-neon shades of red, orange, yellow and green, you’ll find harvest festivals of all kinds, wildlife-spotting ops galore (everything from rutting elk to migrating birds) and seasonal specialties so good, ever more trails keep cropping up as a result (see: the Virginia cider doughnut trail). Plus, a recent spate of local openings and re-openings make 2021 a banner year.

Put otherwise: Now’s the time to grab someone you love and head to Virginia to pursue something you love. Or a whole bunch of things, because connecting the dots is easy. Read on for four of our favorite trails.

If you love …

…Wine tasting

Virginia viticulture goes back so far, it handily predates the US itself: In the Acte 12 of 1619, the House of Burgesses decreed that “every householder doe yearly plante and maintaine ten vines.” By the following century, George Washington, Thomas Jefferson and 36 other enthusiasts had gone in together on the Virginia Wine Company—and a century after that, a locally conceived Norton was named Best Red Wine of All Nations at the 1873 Vienna World’s Fair. Though you’ll find arguably the best place to try modern-day Nortons in Virginia’s horse country (more on that in the next section), the newest and best overview of the state’s wider wine offerings is the 2021 Virginia Governor’s Cup Gold Medal Trail.

Spanning 47 wineries across the majority of Virginia’s seven AVAs (federally-designated American Viticulture Areas), the pours that make up this pathway have been judged the best of the best of the year—and that’s saying something in a state so steeped in winemaking. This mobile passport is a huge help in navigating the trail, but if you want to focus your energies on a few top spots in one area, consider three big winners in the same general neighborhood as Jefferson’s fabled Monticello: Veritas Vineyards and Winery (an idyllic former farm at the foot of the Blue Ridge Mountains, and winner of five golds), Barboursville Vineyards (site of the Jefferson-designed, National Register of Historic Places-listed Barboursville mansion, and winner of six golds); and Michael Shaps Wineworks (a woodsy winery south of Charlottesville, and winner of no fewer than 10 golds).

And autumn, which translates to harvest and crush in the wine world, is not only one of the most bustling times to visit, but also the most beautiful, with the vineyards’ own foliage juxtaposed against the leafy countryside and mountain ranges. In celebration of all of the above, you’ll find festivals throughout October (Virginia Wine Month) and particularly mid-month, for Harvest Party (“Virginia’s home-grown holiday”). For example, Veritas Vineyards is hosting a commemorative Harvest Dinner on October 17, when favorite resident wines will be paired with three courses alongside the fireplace on the patio.

For the most immersive wine-world experience, consider a stay at Barboursville Vineyards’ 1804 Inn and Cottages. The inn, as its name would suggest, dates to the early 19th century, while the cottages range from the 18th century (the Vineyard Cottage) to the 20th (the Sangiovese Cottage). And though there’s a celebrated restaurant onsite, too, you won’t want for foodie finds nearby. In fact, an hour’s drive north—largely along the gorgeous Old Blue Ridge Turnpike that’s now Route 231—will lead you to the state’s prized Michelin-anointed restaurant: the three-starred Inn at Little Washington, where the globally-inspired American cuisine is paired with selections from a 14,000-bottle cellar that has won Wine Spectator’s Grand Award and houses many a Virginia vintage alongside wines from around the world.

…Horseback riding

Known since the 1800s as the Nation’s Horse and Hunt Capital, Middleburg is home to the longest-standing fox hunt in the U.S. (the Piedmont Fox Hounds, est. 1840), Virginia’s oldest steeplechase (Middleburg Spring Races, which just celebrated the big 1-0-0) and a downtown district of tack shops, equestrian art galleries and an inn that dates to the 1700s, when an avid horseman named George Washington visited. Put otherwise, this tiny, tony town is the perfect base for your explorations of the equally equestrian-friendly area it calls home: Loudoun County, which claims more horses—15,000 or so—than any other county in the state.

If you have time for only one major horse trail here, consider the 33-mile bridle path that runs through Washington and Old Dominion Railroad Regional Park—not only because of the wooded beauty, but also because right after you drop off your ride at Chase Run Stables, you can head to the adjacent Firefly Cellars for some acclaimed wine tasting. Another nearby winery pairs horses and grapes in an especially autumnal way: Greenhill Vineyards (a favorite of Michelle Obama’s, among others) will be offering carriage rides through the vines this fall.

Other seasonal equestrian events range from the Virginia Fall Races (October 9) to the Hunt & Hounds Review, a pageantry-packed horseback parade that takes place the first Saturday in December as part of the Christmas in Middleburg celebrations. But if you’re looking for a multitude of horse experiences under one roof, consider a stay at Salamander Resort & Spa by the formidable Sheila Johnson, whose Equestrian Center combines 25 acres of entry-level grounds, a 14,000-square-foot stable and trails and training—and rides of all kinds, including horse whispering. And don’t miss Cupcake, the resident miniature pony, who holds court on the Grand Lawn every Friday and Saturday afternoon.

While Salamander is the height of modern-day Middleburgian equestrian chic, that honor used to go to the nearby Red Fox Inn & Tavern. In the 20th century, none other than Jackie O.—an avid rider—was among the notable regulars here. Indeed, President Kennedy gave a press conference from the inn’s upper tavern—more than 200 years after the very first man to hold his job rode up to the same building. In between George Washington and John F. Kennedy, all manner of visitor turned up here, perhaps most notably, the wounded soldiers who were treated in the tavern turned military hospital during the Civil War. Today’s visitors go for decidedly different reasons: the cozy ambience and the fabulous food, from the fried chicken to the biscuits and mac and cheese.  

For the full historic Middleburg Monty, add stops at the oldest and best known tack shop, The Tack Box; the equine gallery and literary collection at the National Sporting Library and Museum; the local watering hole and pub food favorite, The Red Horse Tavern and the award-winning winemaker that’s determined to restore the aforementioned indigenous Norton grape to the world stage, Chrysalis Vineyards.    

...Scenic driving

Jaw-dropping leaf-peeping drives are something of a state specialty. And two of the most renowned—the Blue Ridge Parkway and Skyline Drive—actually link up at Waynesboro to form a mega-trail of fall foliage. Picture 320 or so miles (217 miles on Virginia’s side of the Blue Ridge Parkway, plus Skyline Drive’s 105 miles) of scarlet dogwoods, red maples, bronze hickories, orange beech, golden poplars and russet oaks set against a mountainous backdrop of evergreen pines, firs and hemlocks.

Given the curving country roads and attendant speed limits, you could cover the entire two-part trail in one long day (nine-ish hours) and experience some of the most glorious sensory overload of your life. But the even better approach is to take two or three days to wend your way through the area, where you’ll find countless gorgeous day hikes, delicious food stops and—this being Virginia—beloved wineries.

Starting at the northern end—mile 0 of Skyline Drive at Front Royal—you’ll drive the along the crest of the Blue Ridge Mountains through Shenandoah National Park.  A few short hikes en route with big panoramic payoff: Blackrock Summit, Bearfence Viewpoint, Hawksbill Summit, Turk Mountain and Compton Peak. This last one actually runs along the Appalachian Trail, but if you’re particularly into AT lore, check out the Appalachian Trail Tanner’s Ridge Road, another short hike that leads to a historic homestead. Between walks, be sure to refuel on the Mile-High Blackberry Ice Cream Pie at Skyland. In fact, this national park lodge—perched at the highest point along Skyline Drive (3,680 feet)—is a great place to stay if you plan to combine a few hikes, or just soak up Shenandoah’s autumnal awesomeness.

Making your way south, don’t miss the great new walk at the junction of Skyline Drive and the Blue Ridge Parkway, 700+ feet below the mountains: the Blue Ridge Tunnel. Once the longest railroad tunnel on the continent, this 2.25-mile time capsule from the 1800s was recently refurbished and reborn as a walking and biking trail.

Once you start making your way along the Blue Ridge Parkway and crave the occasional leg stretch, you won’t want for choice. Among the seemingly endless trails on offer, scenic standouts include Big Spy Mountain, Sharp Top Trail, Roanoke Mountain Summit Trail and Buck Mountain Trail. But if you’re a wine lover, arguably the best place to stretch your legs along the parkway is at milepost 25, where you’ll find parking for the new and aptly named 12 Ridges Vineyard. Walk up the hill to the tasting room, and you’ll be rewarded with not only a sommelier-crafted selection cool climate and sparkling wines, but also foliage-filled views for days.

 ...Music heritage site-hopping

Virginia's Heritage Music Trail—aka The Crooked Road—requires no preexisting passion for Country. The cultural stops are so fascinating, and the Appalachian backroads so beautiful this time of year, even newcomers to the genre can’t help but fall hard. Especially considering that there’s live bluegrass and other old-timey jams at almost every turn.  

The 300-mile trail links dozens of towns, but if you can't hit every last one, try a greatest-hits approach: Starting in Clintwood—ideally after you’ve had a chance to explore the hiking, biking, kayaking and rock climbing in the fall foliage-blessed Breaks Interstate Park—immerse yourself in the life of a bluegrass legend at the Ralph Stanley Museum & Traditional Mountain Music Center,

From there, it’s onto Country Cabin II, where you'll find anything from jam sessions to bluegrass parties with mountain-style clogging lessons before you to proceed to Bristol and the Birthplace of Country Music Museum—all great prep for your next stop: The Carter Family Fold, a memorial to the so-called First Family of Country Music (the family that gave the world June Carter, among others).

For a more modern take on Bristol’s local treasures, head to the bucolic Nicewonder Farm & Vineyards, already beloved for their wines—and soon to open an inn (scheduled to debut this fall). Or consider checking into a historic landmark turned upscale escape: The Bristol Hotel, which occupies a handsome 1925 office building—and which will be replacing traditional in-room robes this September with iconic, locally made L.C. King denim jackets (yup, you can take them home) in honor of the 20th anniversary of the Bristol Rhythm & Roots Reunion (September 10-12).

Then again, you won’t want to miss at least a porch hang and wine tasting at another nearby inn: the historic Martha Washington Inn & Spa (aka the Martha). Nor will you want to miss the Southwest Virginia Cultural Center & Marketplace for its locally-made souvenirs, or the Virginia Creeper Trail, where you hike or bike among stunning, fall-fabulous forests.

Next, make your way to Galax, home to the fabled Rex Theater, whose Friday night Blue Ridge Backroads Live radio broadcasts you won’t want to miss. In fact, weekends bring a whole succession of live events in these parts, not least, the Sunday mountain music and Bluegrass jams at the iconic Floyd County Store. And if you time your trip right, you can hit a legendary annual event in the area: The Blue Ridge Folklife Festival at The Blue Ridge Institute and Museum on October 23, when you can mix it up with moonshiners and mule jumpers, just for starters.

Ready to go? Start planning your next visit to Virginia with these tips.

Related Offers Related Offers & More

More Deals & Tips