Resplendent Roadway

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There are scenic roads in America with mountain, coastal and desert vistas that are ranked by travel magazine advisers who opine as to which ones are “bucket-list,” must-see/must-drives. And then there is the inarguably ideal drive for Kentuckians and Thoroughbred horse lovers (at least this one). I have driven many, many times the 16.9 miles of Ky. Route 1681—Old Frankfort Pike—between Lexington and Frankfort. Trouble me not with rankings and the opinions of the well-traveled. 

For this Louisvillian, any route other than 1681 for an afternoon at Keeneland became unthinkable the first time I ever drove it. Love at first sight wasn’t conjecture or a cliché; it was unavoidable. Where else was I going to see Thoroughbreds grazing in the verdant paddocks that only Kentucky can offer? On my maiden trip, the clincher for me was Thoroughbreds at one farm hanging their heads over plank fencing mere feet from my car. It brought me to a complete stop. There’s only one Ky. 1681.

It’s tempting to employ a cliché that a drive down Old Frankfort Pike is a trip back in time, the only difference being asphalt under your four tires rather than hard-packed dirt under horses’ hooves or carriage wheels. But it’s Kentucky Thoroughbred life today, as it was years ago. That may be a future Kentucky Derby winner or past winner hanging its head over the fence, just like horses in times past, well before the first Kentucky Derby in 1875. 

There is a rich and somewhat surprising history to the Pike. The road is older than the United States, carved into woods of Osage orange, dogwood, redbud, oak and maple between 1775 and 1780. This, of course, pre-dates Kentucky, which became a state in 1792. The road today is home to four properties on the National Register of Historic Places. 

Henry Clay traversed the Pike and stayed at the Blackhorse Tavern, later named the Offutt-Cole Tavern. This former stagecoach stop still stands at the intersection of 1681 and U.S. Hwy. 62 but, alas, no longer hosts travelers. Other personages who are part of the tavern’s history include proprietor Richard Cole’s granddaughter Zeralda, who grew up in the tavern. She went on to marry a Robert James and give birth to two sons: Frank and Jesse. Yep, those James brothers.

Some history pertinent to the Pike, and really to Thoroughbreds in general in Kentucky, is unmarked. Woodburn Farm, now part of Airdrie Stud along the western part of the Pike, was a land grant dating back to 1786 and was the first Thoroughbred farm in what then was the state of Virginia. Thus was the beginning of a road also called—crassly in the opinion of some, including this writer—“Thoroughbred Alley.” An alley Old Frankfort Pike is not.

Traveling from Frankfort, you’ll pass a mile or so of homes and small farms on Hwy. 1681. But things change instantly after crossing the railroad tracks at Duckers Road. Off to the left, a beautiful, solitary barn across pastureland cannot help but capture the eye. You have just left one world for another: pure Kentucky horse country. 

Stonestreet Farm on the left and Adena Springs on the right are the first farms encountered, and the latter farm’s name pays homage to history preceding Thoroughbreds and farms. The Adena American Indians were in this area first, drawn here by free-flowing water from local springs—the ingredient that Kentuckians know produces strong bones in Thoroughbreds and an iconic beverage, bourbon, both indelibly linked to the state’s history and cultural present. The farm is an eight-time winner of racing’s highest honor, the Eclipse Award, for outstanding breeder.

Stonestreet Farm is not without its own claims to fame. Among the farm’s successful runners is two-time Horse of the Year Curlin, the top-earning Thoroughbred at one time in the U.S.—with more than $10 million in purse money won. Curlin now is at stud at Hill ‘n’ Dale Farm. Another Stonestreet star, Rachel Alexandra, 2009 Horse of the Year and Preakness Stakes winner, resides at the farm.

A curve at Adena Springs is a kind of gateway to what many consider the most beautiful part of the drive: a long, straight stretch of farmland with a continuous canopy of trees hedged by hand-laid and mortarless stone fences. 

A portion of Lane’s End Farm on the left is enclosed by the stone fences. One of the more famous names among horse farms, Lane’s End has sold more than 365 stakes winners and has the distinction of breeding and co-breeding two horses—Charismatic and Lemon Drop Kid—that between them won all the Triple Crown races in 1999, with Charismatic taking the Kentucky Derby and Preakness Stakes, and Lemon Drop Kid prevailing in the Belmont Stakes. 

Just past Lane’s End is Airdrie Stud. Five Kentucky Derby winners were bred on this property, but, surprisingly to some Thoroughbred aficionados who know of its history as the site of the first Thoroughbred farm, it also originated the Standardbred horse used for harness racing. 

For Thoroughbred historians, the land is special as home of the stallion Lexington, principal and most famous progenitor of U.S. Thoroughbred racing stock in the 19th century. 

The farm survived the Civil War, which saw armies from both sides routinely confiscate any farm’s horses. Woodburn largely escaped this, thanks, it is said, to a Union Jack flown by Scottish farm owner R.A. Alexander. Union and Confederate deserters, however, were a bigger challenge. The theft of Lexington by some marauders was foiled by a quick-thinking stablehand, who proffered to the would-be thieves a horse closely resembling the renowned sire. 

It’s almost too much to expect, but there is more to Old Frankfort Pike than picturesque horse farms along America’s most beautiful drive. Just past the Pike’s intersection with U.S. 62 is Wallace Station, a bakery and deli that is an institution in the Bluegrass and, for many Keeneland-goers in April and later in October, an automatic stop. The reasons are twofold. For one, the atmosphere and décor are in keeping with Thoroughbred culture, with racing silks and farm logos adorning walls and menu items named for famous horses. The second reason is the food itself. If Old Frankfort Pike is unique to American drives, the Inside Out Hot Brown, which consists of roast turkey, ham, bacon, tomato and white cheddar Mornay sauce, is the Station’s take on a dish original to Kentucky. Also worth a try is the country ham and pimiento cheese sandwich that recently was featured on Food Network’s The Best Thing I Ever Ate.

Past Wallace Station and preceding the Pike’s transition into hillier land is Three Chimneys Farm, one of the most beautiful farms in the Commonwealth, thanks in no small part to stone barns that are somehow both rustic and architecturally elegant. (Three Chimneys, like many horse farms along the Pike, offers tours to visitors.) Three Chimneys is described as a boutique farm, owing to an intentionally limited number of stallions. Among them was the late Seattle Slew, a Triple Crown winner in 1977 who became as successful at stud as he was on the racetrack. 

Gun Runner, 2017 Horse of the Year and the second-leading earner in U.S. history with just under $16 million, is the newest stallion to join the illustrious roster at Three Chimneys. 

Farther along the Pike is an unexpected and delightfully whimsical stop for those wanting to tarry in their travel. As unique as the Pike is for its beauty, the Headley-Whitney Museum is unique in not just Kentucky but maybe the world. Quirky is the first word that might come to mind. The museum houses jewels, dollhouses, shell grottoes and “bibelots,” French for small objects of “curiosity, beauty or rarity,” according to one dictionary. Rotating exhibits give new meaning to the word eclectic, and you never know what you may see. 

Less than a mile down the Pike from the museum, traveling east toward Lexington, is Donamire Farm, picturesque enough to warrant its use as the setting of several horse-related movies. 

Not uncommon for a Thoroughbred operation, Donamire features a 5-furlong training track and a 1-mile European-style turf course. Here, runners are not just bred, they also make their way around racetrack turns and out of starting gates for the first time.

The Pike continues into Lexington, but for me, as for many Keeneland-goers during racing meets, it can end at a roundabout with Alexandria Drive to the right, taking drivers into Lexington and a short drive down U.S. Hwy. 60 to the racetrack. 

The roundabout also affords the opportunity to do what many, especially newcomers to Old Frankfort Pike, most assuredly have done: a 360 around for another look at this most beautiful of American roads.