Fall is arguable the South's best season, when shorter days and the first hint of cool air promise a welcome relief from summertime heat and humidity. We await the changing colors, from green leaves just tipped in yellow to a full-on autumn show of blazing reds, golds, and oranges (if we're lucky and the weather cooperates).
Higher elevations in the Appalachian Mountains explode first, with a wave of color sweeping down from Maryland and the highlands of Kentucky as early as mid-September. The autumn display finally arrives in South Louisiana and Florida as late as November.
Anyone enamored of fall color knows that leaf-peeping is both hobby and sport. Southern routes such as the Blue Ridge Parkway, Skyline Drive, Arkansas Scenic Byway 7, Cherokee Foothills Scenic Highway, and Talimena National Scenic Byway are tremendously popular, forcing vehicles to queue up and drive at a snail's pace. During this annual natural gold rush, vacationers seek out less traveled routes through picturesque small towns that still offer vibrant autumn hues without the distraction of brake lights. You'll find an ideal spot in the Appalachian foothills.
This little hamlet with all the charm and character you could hope for is a great place to anchor your road trip. Orange is in the northern center of Virginia's Piedmont area, known for rolling hills and abundant rivers and streams. The slopes of the foothills offer a gentle transition between the rugged, rocky Appalachian Mountains and the low-lying Coastal Plain of the Atlantic.
Orange County is planted right on U.S. 15, which runs north and south, bisecting Virginia as it meanders across farmland and horse country. The highway is part of the Journey Through Hallowed Ground National Heritage Area, a 180-mile passage from Gettysburg, Pennsylvania, to Charlottesville, Virginia. Rich with both Native American and colonial history, this region is dotted with battlefields and Presidential homes, but you'll also find plenty of modern appeal in the form of local inns, shops, and wineries.
One of this area's most striking inns is owned by Charlene and David Scibal. It was the rural setting, with ample pastures for horses, that initially drew them to Orange. In 2008, the Scibals drove by a fixer-upper estate that was for sale and fell in love with it. Originally built in 1778, the property is listed on the National Register of Historic Places as well as the Virginia Landmarks Register. Reimagined as The Inn at Willow Grove and sitting amid 40 rolling acres, it provides travelers a peaceful sanctuary with spectacular vistas.
A former schoolhouse on-site was transformed into a luxury cottage that retains its historical integrity. Other outbuildings were renovated to serve the thriving wedding market. Eventually, David and Charlene, along with son Matthew as general manager, added the Vintage Restaurant & Pub and a modern spa, as well as bungalows planned with scenery in mind.
"For us, fall is the busiest time of year," explains David as he makes a case for visiting the area. People flock to nearby Shenandoah National Park. "When the trees get lit up, we see views on rolling hills," David says. "It's beautiful, but we have that plus inns, restaurants, and so many things to do."
Forked on Main, which is owned by the inn, serves customers in two distinctive spaces—a cozy dining room and an expansive, well-lit bar—right on Main Street. Chef Kenneth Hughes' menu changes with the seasons, but a couple of dishes have earned permanent billing: the Shrimp and Grits "Our Way" for dinner and the lunchtime Mac & Scratch-Fried Chicken.
For burgers and local brews, check out The Light Well on East Main Street. The tavern serves pub fare and over 40 different beers, including four of their original made-in-the-back brews.
If you're a history buff, this part of Virginia is for you. James Madison was one of eight U.S. Presidents from the commonwealth, and the home he shared with his wife, Dolley, is now called James Madison's Montpelier. This estate offers stunning views of the Blue Ridge Mountains and 2,650 acres to explore, including some 8 miles of colorful walking trails. Thousands of equestrian-minded fans show up here for the annual Montpelier Hunt Races every November.
Madison's Federal-style house was originally built by his father around 1760 using slave labor, but over the years, the property evolved into its current incarnation, which includes the home, visitors center, archeology lab, and historical exhibits. One not to miss is The Mere Distinction of Colour, which details the history of enslaved people at the estate, as told by their living descendants.
The Montpelier Foundation restored a 1910 rail building to create a permanent exhibit, The Montpelier Train Depot: In the Time of Segregation, educating visitors about the social and political inequities of the Jim Crow era.
The Market at Grelen is adjacent to Montpelier—as "next door" as you can be with a few hundred acres in between. This destination garden and market began with a 200-acre farm purchased by Dan Gregg and Zeke Galvin back in 2003. Eventually, the property expanded to 600-plus acres and became one of the largest retail tree nurseries in the state. The farm's thoughtful layout and design received so much praise from visitors that it inspired Dan's wife, Leslie, to join the team and help open a European-style garden shop, pick-your-own farm, cafe, and manicured hiking trails.
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"Fall is my favorite season," she says, laying claim to the ideal spot to enjoy a foliage show at Bloomfield, the height of their property. "You look down the valley of the nursery—we have thousands of colorful trees—and see the Blue Ridge Mountains on the horizon," she says. "One reason our land is so beautiful is that we grow plants on the contour, like an Italian vineyard. It's smart from an agricultural standpoint, as well, preventing erosion."
Browse the inspiring gift shop here (there's a sister store, Grelen Downtown, back on East Main Street), or spend a few hours hiking the 5-mile jaunt through the nursery and meadow. This trail eventually connects with Montpelier's. Follow up with a pick-your-own basket of apples for fall pies and cobblers. Then again, you can just let the cafe do the cooking. Try an "Adult" Grilled Cheese Panini with three cheeses, plum chutney, and bacon. Pair it with a local hard cider. Before you leave, take a picture next to the Living LOVE Sign, one of 150-plus LOVEworks pieces throughout the state, all celebrating the "Virginia Is for Lovers" message. Leslie designed the iconic sculpture—the only living LOVE sign, made entirely of plants grown in a rebar frame.
A highlight of this region is the Monticello Wine Trail, with 33 participating wineries. One noteworthy stop is Barboursville Vineyards. The winery was built by Gianni Zonin on the estate of former Virginia governor James Barbour. Along with winemaker Gabriele Rausse, Zonin successfully established European grapes in Virginia. Since taking over more than 25 years ago, renowned winemaker Luca Paschina has elevated the brand to elite status.
Visit the Tuscan Tasting Room or (for a curated sampling featuring older, cellared vintages and small food pairings) Library 1821. See the impressive ruins of the governor's mansion, designed by Thomas Jefferson. Then enjoy dinner at the celebrated Palladio Restaurant, and settle into a cottage room that overlooks the vineyard at The 1804 Inn.
Proximity to Charlottesville, the Blue Ridge Mountains, and Richmond means travelers often set a course through this village and stay put for dining and shopping. Don't miss the Laurie Holladay Shop, Painted at Poplar Haven, Raindrops in Virginia, and Krecek Kakes Bakery & Coffeeshop.
Just follow the smoke to find The Barbeque Exchange in Gordonsville, helmed by co-owners Donna and Craig Hartman (who doubles as the chef). General manager Stacy Sampson says, "Everything is made in-house—except the ketchup and sodas."