The Bluegrass Loop: A 5-Day Dive into Kentucky's Wild Heart

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Advisor - Marjorie Dufek
Curated By

Marjorie Dufek

  • Kentucky

  • Food & Wine

  • Road Trip Travel

  • Nature Escapes

  • Slow Travel

  • Local Culture

Advisor - The Bluegrass Loop: A 5-Day Dive into Kentucky's Wild Heart
Curator’s statement

How about a road trip that swaps city stress for rolling hills, underground wonders, and fresh air? Kentucky’s got you covered. We’re talking a five or six-day loop through the state’s wild heart: think ancient forests, the world’s longest cave system, Shaker simplicity, a sparkling lake escape, and prancing thoroughbreds, with a taste of bourbon on the side.

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Day 1: Forest whispers & Southern charm

One of the Forest Giants at Bernheim Forest

Louisville to Bernheim Forest

Kick off in Louisville (fly in if you're not local).

Head south 30 minutes to Bernheim Forest and Arboretum, Kentucky's official state arboretum sprawling over 16,000 acres of wild woods.

Wander the canopy treehouse for treetop views, hunt for the giant Forest Giants sculptures, or hike the easy Hemlock Trail, spotting deer and wildflowers.

Afternoon eats

Fuel up with a picnic from the visitor center’s café-grab local cheeses and that Kentucky coffee.

Day 2: Into the Earth's belly

Bernheim Forest to Mammoth Cave

Drive south an hour to Mammoth Cave National Park, where the ground swallows you whole. This UNESCO gem boasts over 400 miles of explored passages-the longest cave system anywhere.

Book a tour through torch-lit halls and hear tales of 5,000-year-old mummies and Civil War hideouts.

Above ground, stroll the Cedar Sink Trail for sinkhole views and river vibes.

  • Tip: Wear sturdy shoes. It's cool and damp down there (55°F year-round).

  • To eat: Picnic at the visitor center or visit the lodge’s buffet for fried chicken.

Day 3: Lake life detour

Mammoth Cave to Lake Cumberland

Drive east 1.5 hours to Lake Cumberland, one of Kentucky’s crown-jewel lakes, with 1,200 miles of shoreline. This massive reservoir’s perfect for unplugging.

  • Rent a pontoon boat for the day for cliff-jumping at Yahoo Falls or fishing for bass.

  • Hit the state resort park for hiking the Sheltowee Trace or a sunset cruise. The water’s warm in the summer; fall’s got epic foliage.

  • To eat: Grab BBQ at a lakeside joint like The Local in Somerset.

Day 4: Timeless tranquility

Shaker Village of Pleasant Hill

Lake Cumberland to Shaker Village

Head east-northeast for 1.5 hours to Shaker Village of Pleasant Hill near Harrodsburg. This 3,000-acre living history site feels like stepping into a 19th-century dream: 34 preserved Shaker buildings amid golden fields.

  • Tour the spiral staircases and herb gardens, catch a blacksmith demo, or hop on a wagon ride.

  • Hike the 33 miles of trails if you’re feeling it, or just breathe.

  • Tip: Enjoy lunch at the Trustees' Table for farm-fresh salads and Shaker lemon pie.

It’s all about that Shaker way of life: simple, honest living. The entire place is peaceful, like the world’s noise got muted.

Day 5: Gallop to the finish

Shaker Village to Kentucky Horse Park

Drive north one hour to Lexington’s Kentucky Horse Park, the ultimate equine playground on 1,200 acres.

Watch Hall of Champions parades with retired Derby winners, pet mini horses in the Gift Barn, or ride a trolley through pastures. It’s a working farm-meets-theme-park celebrating all breeds. Cap your trip with a trail ride or just barn-hopping.

  • To note: Open daily March to November.

Say goodbye

If you flew in, from here you can loop back to Louisville (1 hour), or fly out of Lexington's Blue Grass Airport.

Day 6: Optional extra day

Bourbon day

If your schedule allows, add a “bourbon day” to the beginning or the end of your trip.

To allow you to fully enjoy tasting Kentucky’s finest, schedule a guided tour that chauffeurs you between several distilleries.

  • In the Bardstown area, visit Makers’ Mark, Heaven Hill, and others.

  • In the Lexington area, Woodford Reserve, Buffalo Trace, and Bulleit are just three of the many distilleries in the area.

  • Louisville is the home to Old Forester, Angel’s Envy, and Evan Williams among others.

Need to know

This road trip is designed for relaxation: take it easy, drive slowly, and enjoy the scenery.

Advisor - Marjorie Dufek

Travel Advisor

Marjorie Dufek

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For more inspiration and insider recommendations, visit our Kentucky page.