Exploring the Southeast

Finding Kentucky's Bluegrass

  • Cumberland Falls
  • The Shaker Village of Pleasant Hill
  • Lexington
  • Versailles


October 4 – 8, 2022


  • Accommodation for three nights at the Shaker Village of Pleasant Hill; sumptuous Shaker-recipe meals
  • beautiful Cumberland Falls, including an overnight in the rustic and historic DuPont Lodge
  • Bluegrass scenic touring: drives in horse country; a guided tour of a well-known thoroughbred-breeding farm; visit of an historic distillery
  • Lexington touring: visits to Henry Clay's Ashland estate, the Gratz Park neighborhood, the historic Keeneland Race Track
  • a riverboat cruise on the Dixie Belle: plying the scenic Kentucky River Gorge from Shaker Landing

Trip Description

Let’s head West this October . . . to the “near West” – otherwise known as Kentucky!  We’ll come into engaging contact with some “fine companions”:  Shakers . . . Distillers . . . historic frontier-folk . . . top-shelf architecture and crafts . . . fine foods . . . quaint towns . . . thoroughbred horses . . . and natural beauty!  We’ll spend our first night at the lovely Cumberland Falls in southern Kentucky; and the next three on the sublime grounds of the Shaker Village of Pleasant Hill, near the steep banks of the Kentucky River.  The Shakers were a religious community who thrived in the mid-nineteenth century.  They became known for their craft-skills in producing furniture, finely-constructed buildings, seed varieties, foods and enduring recipes; and for their belief in a simple, hard-working communal life.  The village today consists of several dozen 19th century buildings – in the most delightful of rural settings, groomed “working” farmland, and costumed interpreters demonstrating the skills and cultural folkways of the historic Shakers.  We’ll take one day to venture to Lexington, and to the rich horse country just northwest of the city.  And yes, there’s Bourbon:  We will visit the historic Woodford Reserve distillery.  This adventure will be eye-opening (and quite tasty, too), as we delve into several rich layers of Kentucky’s story.


Day 1

Westward Ho!  That’s the Pioneer Spirit we want – after all, we’re off for Kentucky!  We’ll drive by interstate to the Norris, Tennessee, area where we’ll enjoy lunch, and a great “walking around break” as we tour the acclaimed Museum of Appalachia, established as a great monument of “pioneer” preservation by John Rice Erwin in the 1960’s.  Our drive will take us past the Norris Dam on the Clinch River – birthplace of the Tennessee Valley Authority in 1935.

We’ll continue our drive up and over Jellico Mountain (into Kentucky), then divert from the interstate to Cumberland Falls:  “the Niagara of the South.”  Well . . .

It’s a beautiful place, and graced by a lovely CCC-built stone inn – now all a part of Cumberland Falls State Resort Park.  Enjoy!  You can hike or walk, see the falls, enjoy the down-home comforts of the inn (called The DuPont Lodge) . . . and join our illustrious group for dinner at the Riverside Restaurant.  We’ll spend the night in these historic accommodations, and rest well after an exciting first day of discoveries.

Day 2

Enjoy a good breakfast at our inn, then we depart for points north.  Those will include the historic (c. 1790) house of William Whitley – one of Kentucky’s great frontiersmen / riflemen.  We’ll delight in a guided tour of Whitley’s stone homeplace, then continue to Danville, Kentucky – in the geographic center of the state, and therefore the edges of the famed Bluegrass.  We’ll have lunch, see Centre College, then drive through lovely rolling real estate to the Shaker Village of Pleasant Hill.

We’ll check into our comfortable quarters:  the actual historic buildings of this living history village.  In the mid-afternoon, be sure to join a “top-to-bottom” tour of the village’s most illustrious building:  the Centre Family Dwelling.

You’re in for a treat tonight, because dinner is in the Trustees’ House Restaurant – the heart of the Shaker Village.  Enjoy conversation, the easy rhythms of this special place . . . and pass the salsify!  Overnight at Shakertown.

Shaker Village photos credit:  Shaker Village of Pleasant Hill

Day 3

This morning, the oft-repeated line will be “pass the pumpkin muffins, if you please.”  No worries – there are always more coming out of the oven.

Let’s tour more of Shakertown – plenty to choose from.  Costumed interpreters (and in some cases singers) will take us inside Shaker music, the typical skills of the farm community, African-American life at Pleasant Hill.

In the early afternoon, let’s have a short drive in the neighborhood.  We can lunch in Harrodsburg, and learn something about the pioneer settlement that gathered around Old Fort Harrod – now a reconstructed “fort” and Kentucky State Park.

Those who wish can join your Explore Up Close guides (and other enthusiasts) for exploration of the Kentucky River, where it winds through a deep gorge near Pleasant Hill.  In fact, we’ll board the paddle-wheel riverboat, the Dixie Belle, for a one-hour excursion, hearing plenty of stories from the ship’s captain.

Dinner and overnight, Pleasant Hill.

Day 4

After breakfast this morning, we’ll drive to Lexington – capital of both the Commonwealth and the Bluegrass.  Our visits will include Lexington’s pretty Victorian neighborhoods, Henry Clay’s Ashland mansion (guided tour), and the historic Keeneland horse track.  After lunch, we’ll visit the WinStar Farm – among the most famous of the horse breeding farms in Kentucky (and the world).  After all this excitement and fanfare . . . who’s ready for a tour (and a wee dram?) at the Woodford Reserve Distillery?  Even if you don’t imbibe, Woodford Reserve has a gorgeous campus of historic limestone buildings and “something for everyone.”

We’ll return to Shakertown in the late-afternoon.  Enjoy your last evening in this magical and restorative place.  For the Shakers, it was in part about intentional living – a wonderful inspiration for us, as we explore on.

Day 5

Excuse me, could you pass the pumpkin muffins?  That’s right – I meant it.  We’ll enjoy a hearty Shaker breakfast; and by mid-morning we’ll depart for home.  Our drive will be beautiful.  If we’re “right on schedule” we’ll make a short stop not far off the highway, near Rocky Top, Tennessee.  (Sigh.  You know that’s the third name this place has had . . . always trying to improve its standing in the world a bit.  Hmmm.  I wonder what the Shakers would say about that?)

We’ll break for lunch en route; stretches and pit-stops regularly.  And we’ll all arrive home in time for dinner.  (The trouble is, now we’ve been spoiled by Shaker cooking!)

Woodford Reserve photo credit:  Zhivko Minkov

What's Included

  • Comfortable transportation
  • Accommodation in historic inns (with some stairs) for four (4) nights
  • Breakfasts, 3 lunches, and 4 dinners
  • All activities / admissions per the itinerary
  • Guide and concierge service throughout the trip

Trip Price

$2,557 per person (double occupancy; single supplement, $375)

What's Not Included

Price does not include alcohol, other meals, personal expenditures, 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 www.insuremytrip.com, 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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