Keeneland to Cumberland Gap

Kentucky Fall Ramble

  • Bluegrass backroads
  • Lexington
  • Horse races


October 8 – 12, 2024


  • The refined culture of Lexington – “Athens of the West”
  • The Keeneland horse races
  • Backroads Kentucky: karst topography, horse country, Appalachian culture
  • Stories of early explorers, 19th century tragic figures, and the Commonwealth’s undercard

Trip Description

Kentucky’s calling . . . it’s the whinnies of horses, water coursing along limestone ledges, and ghosts of the commonwealth’s rich past.  Let’s answer their call!  We’ll spend our first night in the famous Daniel Boone Tavern Inn in Berea; then drive via pretty Bluegrass backroads into the capital city, Lexington.  We’ll lodge in a cool uptown hotel, central to most everything.  That will include Gratz Park – an urbanite’s dream, which we’ll explore with a local historian. It also includes Keeneland, Lexington’s esteemed horse racetrack.  We’ll attend one afternoon of the Fall Meet, and it’s quite a delightful spectacle.  We’ll also visit Henry Clay’s beautiful Ashland estate, enjoy local fare and friendliness, and bask in the aura of autumn . . . which pairs nicely with Kentucky Bourbon.  We’ll depart urbane Lexington for Pine Mountain, in Kentucky’s far southeast, for our last night.  Nearby, discover the Cumberland Gap National Historical Park, as well as the quaint towns of Cumberland Gap and Harrogate, Tennessee.

Featured Experiences

Daniel Boone Tavern Inn

Built at a prominent location on the College Square in the heart of Berea where the old Dixie Highway intersected with the campus, Boone has become one of the most famous Kentucky hotels and has been known as a popular destination for travelers of business and leisure alike.

Boone Tavern began humbly with 25 guestrooms, now, the guest room tally is at 63, and an $11 million renovation has upgraded many elements of the property, laying the foundation for another successful century. This award-winning Berea, Kentucky hotel is a member of the Historic Hotels of America and is listed on the National Register of Historic Places.

Pine Mountain State Resort Park

You will be charmed by the skilled craftsmanship of stone and wood throughout Herndon J. Evans Lodge at Pine Mountain Resort, one of Kentucky's first state parks. Each of the 30 rooms has a private patio or balcony to enjoy mountain views. Open year-round. AAA 3-Diamond rating. Rooms are available by late afternoon. Lodge room check-out by 11 a.m., local time. We are now pet friendly! The park also has 21 cottages available.

What's Included

  • Comfortable transportation
  • Accommodation for 6 nights
  • Breakfast, 5 lunches, and 4 dinners
  • All activities / admissions per the itinerary
  • Guide and concierge service throughout the trip

Trip Price

$2,875 / person (double occupancy; single supplement, $695)

What's Not Included

Price does not include alcohol, other meals, or optional trip insurance.

..well-planned, from interesting and fun excursions planned each day, to comfortable lodging and transportation. Our trip leaders, Chumley and Khal, were impressive with their knowledge of each area we explored and gracious in their planning of every aspect of our trips.

Trip insurance safeguards your travel investment, your belongings, and most importantly, you. Though trip insurance is optional, we strongly encourage travelers to purchase trip insurance in the event you have to cancel or leave a trip for any reason. Please note, all trip participants should wait for confirmation from Explore Up Close that the trip has the minimum sign-up required to be a “go” before purchasing travel insurance. Please confirm with Explore Up Close before making any additional travel arrangements.

Once you have received confirmation from Explore Up Close, we recommend contacting a travel insurance provider directly to request a quote and compare pricing and features. You can find other providers that may fit your needs at, or we can gladly connect you with our travel agent.

This trip departs from Greenville / Spartanburg, South Carolina and Asheville, North Carolina. If you live elsewhere, please contact us to discuss travel arrangements, and we will look forward to assisting you!

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