On the cusp of America’s 250th birthday, we’re planning an excursion into the frontier country “over the mountains” and distant from the coastal republic. In Kentucky hollows and by Tennessee creeks, an earthier, more democratic lifestyle took root. We can see it for ourselves in the rustic cabin Abraham Lincoln remembered as his childhood home; and in the pillared mansion Andrew Jackson built on the outskirts of Nashville (and on the back of his enslaved workforce). We can experience its sequel on the Civil War battlefield of Franklin, TN and the restored splendor of nearby Carnton Plantation.

Exactly one hundred years have passed since the trial that captivated a nation: In a remote Tennessee village, William Jennings Bryan and Clarence Darrow debated theories of evolution in the famed Scopes Monkey Trial. We’ll visit the courthouse where it all unfolded. The same 1920’s also gave rise to the uniquely American art form known as Country Music. In Nashville we’ve included a nighttime trolley ride past such landmarks as the Ryman Auditorium and Music Row. In addition, the Tennessee State Capitol and nearby State Museum will immerse us in several thousand years of Volunteer State history.

You can’t get much more American than Churchill Downs or Stephen Foster’s rousing anthem, My Old Kentucky Home. We’ll tour the magnificent estate that inspired Foster’s song and place a bet or two at the racetrack that’s still very much in use today. Also on our itinerary: the Kentucky Horse Park, a kind of Disneyland for all things equine. Plus, the home distillery of that other noted Kentucky export – straight bourbon whiskey (aka Jim Beam). One day we start at Locust Grove, the sprawling home of Revolutionary War hero George Rogers Clark… before visiting Louisville’s ultra-modern, hands-on museum dedicated to another local hero, Mohammed Ali.

Each of our trips has its own theme and flavor. I don’t think any of them has included two such distinctive hotels as The Harpeth, a riverfront hostelry located in the heart of Franklin Tennessee, steps away from all the shops, restaurants and other attractions that make Franklin a destination for history lovers. More elegant still is Louisville’s Seelbach, favored by U.S. presidents for over a century; and a favorite hideout for Al Capone and other bootleggers, one of whom served F. Scott Fitzgerald as the model for Jay Gatsby.

Before there was a United States of America there was an American frontier, a country in the making. This fall we’ve planned a deep dive into that raw land, tracing its development over two centuries. A great way to get ready for the 250th.

“And so we beat on, boats against the current, borne back ceaselessly into the past.” The most famous concluding line in American literature has special relevance for historically minded travelers. Especially in 2025, the centennial year of The Great Gatsby, and the perfect time to experience the opulent world of Fitzgerald’s glamorous bootlegger and the nouveau riche guests who invite themselves to his impossibly lavish parties. The author took his inspiration from Long Island’s fabled Gold Coast, where we’ll follow in his footsteps by visiting no less than five spectacular estates that bear the stylish stamp of Vanderbilt, Marshall Field, Otto Kahn and more.

Impressive as these country houses are, it is their elaborate gardens that set the standard for American landscape design. Moreover, their ready access to scenic Long Island Sound bespeaks a nautical culture, of whaling ships and racing yachts, culminating where the island does – at the Montauk Point Lighthouse, commissioned by President George Washington in 1792. We’ll tour the 110-foot tower with the lighthouse’s historian. Washington knew Long Island intimately, for this was the backdrop that nurtured the Culper Spy Ring made famous in the AMC series Turn, and preserved in multiple sites along the island’s Washington Spy Trail.

And that’s just the start of our planned itinerary. It includes half a day at Theodore Roosevelt’s Oyster Bay home and nearby gravesite. The world class Cradle of Aviation Museum, tracing manned flight from Lindbergh to the Hubble Space Telescope. The birthplace of poet Walt Whitman. An “eco-tour” of Long Island wetlands in specially designed craft. A visit to an oyster farm, where we’ll learn about oyster cultivation and instruction on the best shucking techniques, followed by a waterfront sampling of the region’s prized Southold Shindigs.

Of course, we couldn’t visit Long Island without stopping in the Hamptons, allowing sufficient free time for SHOPPING and lunch in that most rarified of seaside communities. At nearby Old Bethpage Village we’ll experience life in the horse-and carriage era, while the 40,000 square foot Carriage Museum in Stony Brook boasts the world’s finest collection of non-motorized vehicles. Back in Queens we’ll pause at Fitzgerald’s fantastical “Valley of Ashes,” home to two world’s fairs. The Queens Museum, a survivor of both expositions, is historically significant as the first home of the infant United Nations, before the UN moved into its current quarters in midtown Manhattan.

Best of all, Long Island is small enough that we can do all this and more using a single, centrally located hotel – the Hyatt Regency Long Island. You can fly in and out of LaGuardia, where another block of rooms will be reserved for the trip’s start and finish. Mid-May should be a lovely time to explore the history-drenched island, and be “borne back ceaselessly into the past.”