Virginia’s Premier Fall Trails: Wine Tasting, Horseback Riding, Scenic Drives & Music Heritage
Whether you prefer hiking, wine tasting, horseback riding, or scenic country drives, Virginia boasts dedicated trails for every passion. Fall stands out as the prime season to explore them firsthand.
Virginia's iconic autumn foliage redefines trail-blazing with brilliant reds, oranges, yellows, and greens. Beyond the vivid scenery, enjoy harvest festivals, prime wildlife viewing—from rutting elk to migrating birds—and seasonal treats fueling new trails, like the Virginia Cider Doughnut Trail. Recent openings and re-openings make this an exceptional time to visit.
In short, gather loved ones and head to Virginia to indulge in your favorite pursuits—or discover many. Seamless connections between experiences make it effortless. Explore four standout trails below.
If you love…
…Wine tasting
Virginia's winemaking heritage predates the U.S.: In 1619, the House of Burgesses mandated every householder plant ten vines. By the next century, George Washington, Thomas Jefferson, and others founded the Virginia Wine Company. A local Norton grape even won Best Red Wine at the 1873 Vienna World’s Fair. While prime spots for modern Nortons lie in horse country (detailed next), the Virginia Governor’s Cup Gold Medal Trail offers the best statewide overview of top wines.
Featuring 47 wineries across most of Virginia’s seven AVAs, this trail highlights the year’s finest wines in a state rich in viticulture history. The mobile passport simplifies navigation, but for focused tasting near Jefferson’s Monticello, visit Veritas Vineyards and Winery (five golds, idyllic Blue Ridge setting), Barboursville Vineyards (six golds, historic Jefferson-designed mansion), and Michael Shaps Wineworks (10 golds, wooded retreat south of Charlottesville).
Harvest season brings bustling energy and stunning vineyard foliage against countryside mountains. Celebrate during Virginia Wine Month (October), with events like Veritas Vineyard’s Harvest Dinner on October 17, pairing wines with fireplace-side courses.
For immersion, stay at Barboursville’s 1804 Inn and Cottages, from 18th- to early 19th-century accommodations. Onsite dining shines, but drive an hour north via scenic Route 231 to the Michelin three-star Inn at Little Washington, boasting a 14,000-bottle cellar with Virginia vintages and Wine Spectator’s Grand Award.
…Horseback riding
Dubbed the Nation’s Horse and Hunt Capital since the 1800s, Middleburg hosts America’s oldest fox hunt (Piedmont Fox Hounds, 1840), Virginia’s longest-running steeplechase (Middleburg Spring Races, 100+ years), and equestrian shops in a historic downtown visited by George Washington. Ideal base for Loudoun County’s 15,000 horses.
Top trail: the 33-mile bridle path in Washington and Old Dominion Railroad Regional Park. Post-ride at Chase Run Stables, taste wines at nearby Firefly Cellars. For fall flair, Greenhill Vineyards offers carriage rides through vines.
Events include Virginia Fall Races (October 9) and Hunt & Hounds Review (early December). Base at Salamander Resort & Spa by Sheila Johnson, with equestrian center, trails, and resident pony Cupcake. Historic Red Fox Inn & Tavern drew Jackie O. and JFK; now famed for Southern comfort food.
Complete with The Tack Box, National Sporting Library and Museum, The Red Horse Tavern, and Chrysalis Vineyards reviving the Norton grape.
…Scenic driving
Virginia excels in leaf-peeping drives. Blue Ridge Parkway and Skyline Drive connect at Waynesboro for 320 miles of vibrant fall colors amid evergreens.
Drive in a day for overload, but stretch to 2-3 for hikes, eats, and wineries. From Front Royal’s Skyline Drive through Shenandoah National Park: hikes like Blackrock Summit, Hawksbill. Refuel at Skyland lodge (3,680 feet). South, explore refurbished Blue Ridge Tunnel trail.
Parkway highlights: Big Spy Mountain, Sharp Top. Wine stop at milepost 25’s 12 Ridges Vineyard for views and cool-climate wines.
…Music heritage site-hopping
The Crooked Road—Virginia’s Heritage Music Trail—captivates with cultural sites and scenic roads, live bluegrass everywhere. No prior fandom needed.
Start in Clintwood post-Breaks Interstate Park, at Ralph Stanley Museum. Then Country Cabin II jams, Birthplace of Country Music Museum in Bristol, Carter Family Fold.
Nearby: Nicewonder Farm & Vineyards, The Bristol Hotel (denim jackets for festival), Martha Washington Inn & Spa, Southwest Virginia Cultural Center, Virginia Creeper Trail.
Galax’s Rex Theater, Floyd County Store jams, Blue Ridge Folklife Festival (October 23).
