The Tennessee Whiskey Trail strings Jack Daniel's, George Dickel and Uncle Nearest distilleries within a 90-minute drive of Nashville. Each runs a kitchen or pairs with a nearby restaurant.
Tip: Uncle Nearest in Shelbyville is the easier reservation; Jack Daniel's tours book a week ahead. Bring a designated driver for tastings.
Franklin's restored Main Street, 25 minutes south of Nashville by car, runs a tighter restaurant row than its size suggests. Puckett's Grocery and Gray's on Main are the institutions.
Tip: Park on 4th Avenue South for free; Main Street meters fill by 11:00. Gray's on Main is the easier reservation than Puckett's for groups.
Lynchburg, 75 minutes southeast of Nashville, hosts the Jack Daniel's distillery and Miss Mary Bobo's, a 1908 boarding-house Southern lunch in a single sitting per day.
Tip: Miss Mary Bobo's lunch books weeks ahead; sign up for the distillery tour at the same time. Lunch seatings are 11:00 and 13:00.
Leiper's Fork, 40 minutes southwest of Nashville, is a single-street country village with the Country Boy restaurant for biscuits and the Fox & Locke for Saturday-night live music and food.
Tip: Sunday brunch at the Country Boy is the marquee meal; cash and card both welcome. Fox & Locke books concert seatings ahead.
Chattanooga, two hours southeast of Nashville by car, runs a strong riverfront dining scene with Easy Bistro for French-leaning plates and Main Street Meats for whole-animal butchery.
Tip: Make a weekend of it; Lookout Mountain views and the Tennessee Aquarium are nearby. Drive back via Sewanee for the scenic route.