Heading into or out of Nashville by car, there are plenty of unique things to explore, including scenic hills, historic battlefields, and a heck of a lot of whiskey. Try these adventures before or after you get your fill of Music City, or plan a day-trip from town if you’re staying for 3 or more days. If you’re looking for maximum impact and minimum headache, consider using one of the excellent companies listed in this chapter to outsource the planning and transportation.


The first thing you need to know about Tennessee whiskey is this: All Tennessee whiskey is bourbon, but not all bourbon is Tennessee whiskey. Originally named for Bourbon County, Kentucky, where it was first distilled, bourbon is made the same way Tennessee whiskey is, but the latter is also charcoal-filtered, which is the crucial step that gives Tennessee sour mash whiskey its smooth, mellow flavor. While the tastings at the two distilleries below are small enough that they won’t necessitate a designated driver, Mint Julep Tours offers several packages, departing from the Omni Hotel, if you don’t want to deal with driving.


If you visit Lynchburg, make a reservation (weeks or even months in advance, mind you) to eat lunch at Miss Mary Bobo’s Boarding House Restaurant. The grand white antebellum-style mansion opened as a boardinghouse back in 1908. Today it serves family-style meals to whiskey-seeking pilgrims from all over the world. Incredibly well-versed and genial hosts join diners for lunch, giving them the history of the area and answering any questions as people serve themselves off giant Lazy Susans. As someone who grew up eating small-town Tennessee comfort food, I can confirm this is the authentic, soul-warming food the South is famous for, and for $25 per adult and $8 per child ages 8 to 12, the portions are also true to Southern style (read: enormous). But if you go on a day when they’re serving mac and cheese or roasted pork, consider yourself truly blessed. They also have the world’s best chess pie, a seemingly simple dessert made with eggs, sugar, and butter supposedly thrown together by a shorthanded cook on a whim. The name has two origin stories: One is that the word is “chest,” pronounced with a drawl and describing the fact that these pies contain so much sugar they can be stored in a pie chest rather than a refrigerator; the second is that the cook who created them was asked what she was baking and replied: “Jes pie.” Whatever you believe, believe this: Mary Bobo’s Jack-Daniel’s-whipped-cream-topped chess pie is a paragon of the art form. 


About an hour outside Nashville and halfway to Chattanooga, you’ll find two of Tennessee’s most fascinating and unique music venues. The Caverns, located at the base of Monteagle Mountain (555 Charlie Roberts Rd., Pelham, TN; tel. 931/516-9724), is the new home of Bluegrass Underground, an Emmy Award–winning subterranean concert series that airs on PBS and features performances by bluegrass musicians such as Billy Strings and Trampled by Turtles. Previously, the series was housed in the nearby Cumberland Caverns Volcano Room (437 Cumberland Caverns Rd., McMinnville, TN; tel. 931/668-4396). Both are stunning venues in which to see live music, but there are key differences. The Caverns is more concert-goer friendly with permanent bathrooms, beer for sale, and a less difficult entry than Cumberland Caverns, which will be difficult or impossible to access for those with mobility issues. The Caverns, however, don’t offer quite the same secretive majesty of the Volcano Room, so weigh your options.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.