Leiper's Fork, the Old Trace & Arrington Vineyards

Leiper's Fork sits along Old Hillsboro Road — one of the oldest roads in Tennessee, predating statehood — in the rolling farmland 10 miles southwest of Franklin. A single block of antique shops, art galleries, and studios occupies a cluster of historic commercial buildings that collectively house one of the most interesting collections of Tennessee folk art, Civil War relics, handmade jewelry, and mid-century furniture in the region. The village has long attracted country music artists and Nashville creative professionals who value its authentic, uncommercialized character — several well-known musicians maintain farms in the surrounding hollows. Morning is the best time to browse, before day-trippers arrive from Nashville and Franklin.

Near milepost 428-430, the Natchez Trace Parkway preserves a section of the original sunken Trace — worn 6-8 feet below the surrounding terrain by at least 10,000 years of continuous foot traffic, from Native American trade routes to the footpaths of 'Kaintuck' boatmen who walked the 444 miles from Natchez back to Tennessee after floating their flatboats down the Mississippi. A short walk on the old trace through old-growth cedar and hardwood forest brings the pre-highway era of American travel into immediate, tactile focus. The parkway itself — a two-lane National Scenic Byway with no commercial traffic, no stoplights, and no billboards for its entire length — is one of the great American driving roads.

Co-owned by country music legend Kenny Chesney, Arrington Vineyards occupies 75 rolling acres in the Arrington community and has established itself as one of Tennessee's premier wine destinations since opening in 2007. The estate produces a range of wines from Tennessee grapes — Chambourcin, Vidal Blanc, Traminette, and the native muscadine — and the tasting room is unpretentious and welcoming. Weekend afternoons frequently feature live acoustic music on the hillside lawn, where visitors spread blankets and enjoy the sunset views across the western ridgelines. The vine-draped pergolas and rolling hills create an atmosphere that is genuinely pastoral without being artificial.