Concierge.com's insider take:
Leipers Fork has a shabby-chic appeal—with the emphasis on chic: This bucolic country village of just 500 is home to some of Middle Tennessee's wealthiest residents, including country-music moguls and a few Hollywood stars, such as Ashley Judd. Despite the high-dollar real estate (farms around here sell for tens of millions), the draw of the Fork is its down-home charm. Highway 46 (also known as Old Hillsboro Road) is the main thoroughfare, and it's lined with galleries featuring work by local artists and quaint antique stores offering high-end American and European furniture and accessories. Leipers Fork is also a popular pit stop for those hiking or driving the nearby Natchez Trace—the terminus of this 444-mile scenic parkway is just 14 miles north of town—or simply looking to ogle prime real estate. For a real (and literal) taste of area hospitality, stop by Puckett's Grocery Store, a triple-threat supermarket/performance space/meat-and-three restaurant located on the main drag. Order the fried catfish—crispy and delicious—and enjoy live music from local artists both famous and on-the-rise on Friday and Saturday nights (4142 Old Hillsboro Rd.; 615-794-1308; www.puckettsgrocery.com). Too tired to drive back downtown? Book a room at the Namaste Acres B&B.