Nashville, Tennessee, To Asheville, North Carolina

Pies at Marché Artisan Foods in Nashville

ROUTE: Fly into Music City and feast on southern eats, updated and old-school, before heading east through the Smokies and into the artist enclave of Asheville.

Go "new Southern" for breakfast at Capitol Grille (a fried egg on Jack Daniel's-infused toast smothered in tomato gravy) and go classic for lunch—a "Meat and Two" plate of roast beef, turnip greens, and mac 'n' cheese at Arnold's Country Kitchen. Come nightfall, head to City House for Mediterranean-meets-Antebellum dishes (pizza topped with house-made belly ham) or to The Catbird Seat for inventive comfort food (beef short ribs with kale ashes and black truffles).
Crash here: Hutton Hotel, a sleek getaway bordering the Vanderbilt University campus.

Wake up with egg-and-roast-pork-loin hash (and grab a slice of chocolate-walnut pie to go) at the Euro-styled Marché Artisan Foods, working up your courage for lunch at Prince's Hot Chicken: a cayenne-scorched breast speared to a slice of bread with a toothpick of pickle chips. Head east, pit-stopping at Countryside in Vonore for a David Chang favorite—Benton's Smoky Mountain Country Ham—served with fried okra and coleslaw. At sunset, pull into Blackberry Farm for "foothills cuisine" like seared North Carolina trout with ham-hock broth.
Crash here: Blackberry Farm, a plush estate and brewery.

Weave your way to Asheville for fried-green-tomato napoleons at Early Girl Eatery, then grab a lunch of southern pub grub (roast-beef po' boy, Appalachian egg rolls) at Tupelo Honey Cafe. Come witching hour, hit Cúrate for small plates like North Carolina clams and house-cured olives before heading to The Admiral for a dinner of roasted quail atop cheesy grits.
Crash here: Grand Bohemian Hotel, a sprawling Tudor lodge.