BRING: Hiking boots, camping gear, headlightHIGHLIGHT: Going deep in Mammoth CaveSOUVENIR: Bottle of Corsair Triple Smoke whiskey (corsairartisan.com)Day OneStart at Bad Branch State Nature Preserve, a chunk of Pine Mountain owned by the Nature Conservancy. You’ll hike a seven-mile lollipop loop through the preserve, which yields the 60-foot-high Bad Branch Falls set inside a sandstone gorge, and an incredible view of the Cumberland Plateau from High Rock, a sandstone outcropping on the crest of Pine Mountain.Post-hike, head eight miles north to Whitesburg, Kentucky’s hippest mountain town, for a scratch-made dinner at Courthouse Café (606-633-5859). Don’t leave without a slice of their signature Tanglewood Pie, a banana, cream cheese, and blueberry blend of goodness. If you like Whitesburg’s vibe, stick around for a show at Summit City, which pulls some of the best yet-to-be-discovered bands touring the South.Pitch a tent lakeside at Carr Creek Lake State Park ($20), 15 miles west of Whitesburg.Day TwoHead 2.5-hours southwest to Big South Fork National Recreation Area, a 125,000-acre park split between Tennessee and Kentucky that has one of the wildest rivers in the South and a high concentration of sandstone arches. Set up camp at the Blue Heron Campground ($17 a night), which will give you quick access to the park’s highlights in Kentucky.Spend the afternoon knocking out the Blue Heron Loop, a 6.5-mile hike that begins with two big overlooks of the Big South Fork River before dropping through a narrow slot in a cliff dubbed “crack in the rock.” You’ll also pass through a mining museum that details the area’s coal history and drop to the river where you can lounge on the giant slabs at Devil’s Jump rapid. Bring some food; there’s not much in the way of restaurants in this remote corner of Kentucky. Day ThreeHead two hours farther west to Mammoth Cave National Park, where the largest known cave system (400 miles and counting) sits below ground. Get there early enough in the day to join a Wild Cave Tour, a full-day, full-contact exploration of some of the wildest areas of the cave. This is legit caving—climbing, crawling, and squeezing through five miles of underground passages and rooms. ($48)After you emerge from the deep, head 30 minutes west to Bowling Green for a tour of small batch bourbon maker Corsair Distillery ($8).Enter our Kentucky Getaway Giveaway to win a FREE adventure road trip to beautiful Pennyrile Resort State Park!Want more adventure? Check out our full list of road trip guides!