Old Frankfort Pike

Old Frankfort Pike

Back in 1963, a song by Nat King Cole rose to Number #3 on the US Billboard Chart. Lazy-Hazy-Crazy Days of Summer was a paean to carefree days “of soda and pretzels and beer.” A time when the freedom of the open road stretched to the horizon and possibilities were endless.

This summer, our 16-county Bluegrass Region invites visitors to recreate those halcyon days on backroads and scenic byways that will bring back that spirit of youthful adventure.

Instead of a time of soda and pretzels and beer, make it a time of Ale-8 and bourbon balls and beer cheese, and while we love Nat King Cole, make the soundtrack for your trip one of the region’s own – Woodford County’s John Conlee or Montgomery Gentry and J.D. Crowe from Lexington.

In the spirit of endless summer and just in time for the Bluegrass Region’s incomparable spring, we offer five scenic routes for you to get lost on.

Old Frankfort Pike (Fayette County and Woodford County, with detours to Franklin County and Anderson County):

Old Frankfort Pike, originally known as the Old Lexington-Frankfort Road, has been in existence longer than Kentucky has been a state. Work on the Pike began in 1775 and was completed in 1780, preceding statehood by 12 years.

In 2021, Old Frankfort Pike was named one of America’s National Scenic Byways, the first in the Bluegrass Region to be so honored. This route offers not just outstanding natural beauty, but also archaeological, cultural and historical significance, as well as a myriad of recreational opportunities – all in a landscape found in practically no other part of the country.

This scenic byway and others like it - often described as “the roads less traveled” - are perfect for leisure exploration, whether you’re a solo adventurer or on a family vacay; whether you have 24 hours or 24 days (yes, there really is that much to do in our 16 counties).

If you haven’t driven Old Frankfort Pike lately, you can celebrate this honor and see some of the reasons for it.

Start at the Distillery District in Lexington in Fayette County, and see the remarkable re-development of what was the city’s oldest bourbon distillery.

More than a century ago, this was the site of the James E. Pepper Distillery, and one remaining landmark, a rickhouse used for aging bourbon, has undergone renovation and now houses several restaurants, bars and businesses.

Once again, bourbon is being distilled here (Barrel House Distillery); consumed here (The Break Room and Elkhorn Tavern) and celebrated here in a gritty atmosphere with a hint of yeast in the air.

But the District is not just about bourbon. Stop for a beer at Ethereal Brewing, a pizza at Goodfellas Pizzeria or an ice cream cocktail at Crank & Boom Craft Ice Cream.

If you want to make Lexington your base, book a room at The Manchester, the Distillery District’s signature property, which describes itself as “a monument to Lexington’s unbridled enthusiasm, warm southern light and full-galloped feeling.”

Rinse off the trail dust with a Tiki Holler or Cabana Banana at the hotel’s rooftop Lost Palm cocktail bar before heading to dinner at its Granddam Restaurant. You’ll know you’re in Kentucky if you order the buttermilk-brined fried chicken with house-pickled slaw.

Leaving the Distillery District, a short detour off  this portion of the Pike leads to McConnell Springs, where Lexington began in 1775, and now a 26-acre serene oasis on the outskirts of downtown.

Take time to wander its two miles of trails where the floral carpet is woven with blue flag iris, pink swamp milkweed, scarlet cardinal’s flower and lavender appendaged waterleaf.

Hikers can also encounter urban wildlife that calls the Springs home – from box turtles and garter snakes to sharp-shinned hawks and shy red foxes.

But the real draws are the two natural springs – the Blue Hole and the Boils. The former has been a source of mystery since its earliest discovery by Native American tribes who marveled at the electric blue of the water.

Back in the car, head away from the city and when you reach the roundabout connecting Old Frankfort Pike and Alexandria Drive, dominated by the statue of Triple Crown-winning Secretariat, notice how the landscape shifts from urban to rural.

Horse Country, U.S.A.

This is horse country at its best, with famed Thoroughbred farms such as Darby Dan, Stonestreet, Donamire and Windhaven stretching along both sides of the road. Both Darby Dan and Stonestreet are open for tours.

Other farms open for touring on or near Old Frankfort Pike, including Airdrie Stud, WinStar, Lane’s End and Three Chimneys. All bookings must be made through visithorsecountry.com)

Just past Donamire is one Old Frankfort Pike site that you can visit on your own. The Headley-Whitney Museum, with its one-of-a-kind jeweled bibelots, is a unique Bluegrass Region attraction. After oohing and aahing at the jewels, you can also visit the Mary Lou Whitney Rose Garden and the Shell Grotto.  (Because opening hours are erratic, it’s best to check before going.)

Continue driving and cross the Fayette County line into Woodford County where another brief detour will take you to Weisenberger Mill, one of Central Kentucky’s most photographed spots.

Straddling the Woodford/Scott County line on the South Elkhorn Creek, it is the oldest continuously operating grain mill in Kentucky, with a structure dating as far back as 1818 (the current one dates to 1913.)

This is the perfect place to pause for a photograph of the honey-colored mill and its rushing milldam. If you stop for breakfast along this route, you are likely to find Weisenberger Mill grits on the menu – go ahead and try them; you won’t be sorry.

Back on Old Frankfort Pike, a completely different kind of attraction, Mt. Vernon Baptist Church, is an example of both the Pike’s architecture and history. The red brick church is done in a faux Romanesque style and upon examining the plaque, you’ll note that it was built in 1822 and is still in use today.

This Woodford County stretch of the Pike is also a good place to see examples of the Bluegrass Region’s iconic rock fences. These fences, made by artfully piling the stones on top of each other without the use of mortar, were first built by 18th century settlers, and later by Scottish and Irish immigrants to the region.

The fences prove a fitting frame for more sprawling Thoroughbred farms; one of the most famous is Three Chimneys, long-time home to Seattle Slew, the only undefeated Triple Crown winner.

History and Hot Browns Await on the Pike:

If by now you’re getting a little hungry, there’s no better meal stop than Wallace Station. Not only does it offer the best of deli and bakery options, the building itself is a historical treasure. 

Listed on the National Register of Historic Places, it was built in the early 20th century and served as a store providing goods to residents of the nearby town of Midway.

In addition to serving up Kentucky favorites such as fried catfish with Weisenberger hushpuppies and the Inside Out Hot Brown (roast turkey, ham, bacon, tomato and white cheddar mornay), the building has many stories to tell.

One of those involves Dora Brock, the young bride of emancipationist Cassius Clay, who, upon her death in 1914, had her wake held in the store. 

Another compelling slice of history can be found nearby, at the Pike’s intersection with US 62. The white Colonial-style Offutt-Cole Tavern dates back nearly 250 years and has been a tavern, a stagecoach stop, and one-time home of Zerelda Cole, mother of Frank and Jesse James.

It is not open to visitors, but that won’t stop you from imagining the excitement generated when the notorious outlaws stopped by to visit their mother.

If you turn left off the Pike, you’ll have a chance to see one more of the Bluegrass Region’s premier Thoroughbred farms, Lane’s End.

If you opt to turn right, a short drive will take you to Midway, regularly found on Kentucky’s list of most charming towns. Midway got its start in 1831 as the first town in the commonwealth to be established by a railroad (its name comes from being the midpoint between Lexington and Frankfort on the Lexington & Ohio Railroad Route).

Midway’s history includes not only occasional sightings of the James Brothers, but guerilla raids by Confederate general John Hunt Morgan and the notorious Sue Mundy, and a visit by General George Armstrong Custer, who came to Woodford County on the lookout for prime equine stock for both the U.S. Army and his personal breeding operation.

Roadtrippers will be enchanted by the Victorian-style buildings painted in ice cream sherbet colors that line both sides of the railroad track. These buildings house restaurants (Heirloom, The Goose & Gander) and unique shops (Historic Midway Gift Store, where you can pick up a souvenir of the region, and Crittenden Rawlings, where men can take their leave decked out like Southern gentlemen).

Take a Detour for Bourbon Balls and Bourbon Barrels (they’re not what you think):

Old Frankfort Pike doesn’t go all the way to Frankfort, instead culminating at US 60. Since you’re this close and if you’re not ready to stop for the night, turn left on US 60 and on the right side of the road you’ll find Rebecca Ruth Candy Retail Store #3.

Load up on sweet treats for the road (bourbon balls are the specialty), and if you find yourself curious about just who Rebecca and Ruth were, a museum dedicated to their candy-making skills is just a short drive away in Kentucky’s capital city of Frankfort.

(For the record, Rebecca and Ruth were Rebecca Gooch and Ruth Hanly Booe, two substitute school teachers who began their candy business in 1919 as a side hustle to supplement their teaching salaries.) 

Note: It might be of interest to know that the two savvy candymakers became female entrepreneurs before they became female registered voters. It wasn’t until the following year that the 19th Amendment, giving women the right to vote, became law.

From chocolate tasting to wine tasting is a short hop on US 60 in Franklin County where you’ll arrive at Prodigy Vineyards. This 62-acre vineyard and winery is located on a picturesque family farm in the midst of Thoroughbred country.

Winery staff invite you to “uncork a Bluegrass legacy” with their Vidal Blanc, Cabernet Franc or Chambourcin. The latter, made from grapes grown on the property, has been voted Best Dry Wine in Kentucky.

As long as you’re this close, take another detour into neighboring Anderson County where it’s back to bourbon. The county has a long and storied distilling history going back 200 years (you may already be familiar with Wild Turkey and Four Roses distilleries).

You may not be as familiar with Larrikin Bourbon Company, the first craft distillery to open in Anderson County. For the uninitiated, larrikin is an Australian term used to describe someone who is mischievous, rowdy or unconventional.
    
Now, we’re not saying that husband and wife owners Greg and Katie Keeley are mischievous or rowdy, but they are certainly unconventional.

Greg, an Australian, and his American spouse are the first members of the military to own a Kentucky distillery. And what else can you say about a couple whose first employees were their dogs – a Red Doberman as Chief of Security and an Australian sheepdog as Chief of Morale?

Now that you’re in a bourbon frame of mind, you’ll be happy to know that in Anderson County you can curl up in a bourbon barrel and drift off to sleep with dreams of the Angel’s Share dancing in your head.  Well, sort of.

You’re not exactly nodding off in an American oak barrel. Rather, you are at Bourbon Barrel Retreats, sleeping in well-equipped cabins shaped and designed to resemble bourbon barrels. These barrels, however, are 300 square feet – enough to accommodate a king-sized bed, a separate kitchenette and bathroom, and in some cases, a deck with a hot tub. 

Even if you aren’t one of the lucky hot tub lottery winners, there is still the fire pit in the communal area where overnighters sit, sip and swap bourbon stories.

This summer, why not kick your road trip into high gear with a drive along Kentucky’s and America’s  Scenic Byway, Old Frankfort Pike.

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Photo: Wallace Station Deli and Bakery, Versailles

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