This article was originally published in the February 2003 issue of Motorcycle Cruiser.

"BAKED POSSUM WITH SWEET POTATOS," read the scrawled sign in the window of the building next door. I'd stopped in front of a forlorn service station somewhere off Route 421 deep in the Daniel Boone National Forest, on my way to the Hoot. I was hopelessly lost in Kentucky, but if I was hungry, I quickly lost my appetite after reading the menu board. (Though I admired this unique approach to controlling the local critter population.)

After a few colorful exhortations from the tolerant station owner (something about turning left at the holler, right past the crick), I was back on my twisted path south, relieved to find out that I hadn't strayed far off the mark -- I'd just been going in small circles.

I had started my June journey toward the Bluegrass State along State Route 41, an engaging blend of switchbacks and sweepers that meanders through south-central Ohio before morphing into US 68 at the Ohio River. I had planned on taking the long way to the Hoot, forging through Kentucky down to Colonel Sanders' Cafe in Corbin for some serious finger-licking, then continuing on to Knoxville. It turned out to be a longer jaunt than I'd envisioned.

Kentucky bridge
Impossibly green water breaks up the expanse of the Kentucky forest.Andrew Cherney

Just across the south side of the river I hit Maysville, Kentucky -- a half-quaint, half-homely river town with the lethargic quality of a fighter who's taken too many blows. Part of northern Kentucky is covered with lush, pristine forests, but this was not that part. For a dozen miles along US 68, I was in the down-on-its-luck, strip-mall-on-every-corner, already-hot-at-10-in-the-morning part. The closer I got to Lexington, though, the softer the edges of despair became, and the slower I found myself traveling -- suddenly there was eye candy everywhere. As I skirted Paris, with its rolling acres of horse farms and shag carpet of bluegrass, I found all stereotypical preconceptions of fried chicken, hillbillies and bourbon receding into the idyllic landscape. Like most knuckleheaded Northerners, I'd always believed Kentucky was the Deep South (even though it never seceded from the Union). It was only now that I could feel the difference.

By the time I rolled into Lexington, my head was spinning with postcard scenes of Bluegrass Country, all antebellum architecture faded against fields stocked with powerful thoroughbreds. They do love their horses here -- after miles of dry-laid rock fences and historical districts, I stumbled upon the Kentucky Horse Park, where legendary racehorse Man O' War's 28-foot stride is memorialized (the museum is a must for horse fanatics). But Lexington isn't just a bed of southern gentility -- it's also a diverse city whose university population lends a cosmopolitan edge. That's why I chose it to be the starting point of my scenic loop.

Kentucky Horse Park
If you have an interest in horses other than the iron ones, Kentucky has farmlands of thoroughbreds, not to mention the Kentucky Horse Park.Andrew Cherney

Since I was spending the night, I found time to linger over a southern-fried dinner of banana peppers (sliced, breaded and fried) and catfish (or was that possum, I wondered) at Hall's-on-the-River, a few miles out of town. The chow was overdone, but the lull of the Kentucky River rushing by the patio made the sticky evening perfect. In the morning, I made a point of stopping at stately Ashland, the Henry Clay estate, downtown. The well-preserved, Italianate-style manse of Kentucky's greatest statesman is a National Historic Landmark bulging with fascinating period collections, but I couldn't dawdle; the demands of urbanity were already wearing on me. I wanted to get back to the riding.

After a quick tour of the Ashland estate, I twisted east out of Lexington along US 60. The roadside tapestry of horses, bluegrass hills and hay bales blurred into a rural kaleidoscope, and I remember thinking, wow bluegrass really is least from far away. A local rancher informed me that the grass produces bluish-purple buds in springtime, giving it a blue cast. Who knew...

Twenty bluegrass miles later, I found myself in Winchester, a charming hamlet that has seen better days. It isn't chewed-up like other old towns, though; a few restored buildings combined with an easy pace give this sleepy burg an endearing quality, and I remember feeling supremely relaxed here -- until I missed the turnoff for State Highway 89. Lost again. After circling around the town (I later discovered the sign for 89 was hidden behind a tree), I stumbled upon the elusive route and hightailed it toward the Daniel Boone National Forest.

Kentucky Road
Road notes: Road conditions vary—watch for gravel, hay and, er, wildlife in blind corners.Andrew Cherney

Success at last. Blasting through the Bluegrass State here was the height of freewheeling -- no shoulders, no paint, just the rumble of a bike and the heavy air of the South on your face. Rural Kentucky's laconic rhythms were appealing, and the farther south I traveled, the narrower 89 became. At one point I was almost completely hemmed in by flora -- brushing shoulders against nosy goldenrod, crowding tulip trees out of my way and playing chicken with the hanging vines.

The terrain changed near the sprawling Daniel Boone National Forest a half hour later, as I left flatter bluegrass country for the more mountainous Eastern Highlands. Though it's heavily visited, you won't ever feel crowded in the Boone Forest -- it's rugged, with forested ridges, narrow valleys and an abundance of rivers (Kentucky has more running water than any state except Alaska). A misstep in this remote area can be serious, though, so I chose my route to parallel Interstate 75, a few miles to the east. If I needed to make better time, I merely had to jog a couple of miles over and blast down the superslab. In theory, anyway.

Kentucky barn
Check for signs at every intersection—State Highway 89 runs all over the place, and no one really knows where.Andrew Cherney

Scattered in the forest amongst the sugar maples and white oaks were pools of impossibly green water, occasionally broken up by clear creeks bursting with trout. Officially (or so the map says), the scenic part of Scenic Byway 89 doesn't start until Irvine, some 40 miles south of Winchester, but I was pretty impressed by this point. Of course, my map couldn't possibly accommodate all the secondary back roads I found myself eagerly sampling near the tiny town of McKee, and that's about the time I stopped for directions -- and was greeted by the Possum Special. Remote routes in this forest unroll haphazardly, so I was lucky my charting blunder propelled me into the small community of Berea. It was a treat to cool my jets and rehydrate in the shadow of Berea College, where student-artisans work on campus in lieu of paying tuition, showcasing their arts and crafts around town. On a student's recommendation, I ducked into Boone Tavern, in an historic old building off Main Street. True to form, it proved the perfect place for a drink and an authentic Southern meal. I grinned at my good fortune.

Back on 89, I picked up the Scenic Byway portion of the ride just past McKee. If you weren't satisfied with the road's fast sweepers, tight switchbacks and gorgeous greenery til now, this is where things got really interesting. It seemed the county just gave up supplying this stretch of asphalt with the usual trappings of modern roads -- traffic signs, lane markings and even shoulders became wishful thoughts. It was essentially a paved path through the woods, and vegetation had the right of way.

Kentucky mansion
Even if you lose your way, eye candy can be found speckled across the state.Andrew Cherney

Make sure you don't guess wrong on the turns either, because this trail is quite literally a zoo. Screaming around one corner, I came upon what looked like dark green bricks scattered in the road. I swerved, but when they somehow moved back into my path, I almost lost it. Turns out they were turtles sunning themselves on the blacktop. I nearly plowed into a dog curled up on the asphalt and a family of quail here, too. And then there was that rickety wooden bridge...

Kentucky bridge
Much of the 89 has no shoulder or pullouts or is one lane.Andrew Cherney

If you do manage to emerge unscathed from the canopy of trees on this one-lane path, don't miss the unmarked fork in the road ahead like I did. At the end of 89, I abruptly came to a fully realized (read: paved and painted) two-lane highway. I later discovered I should have veered right (State Highway 490), proceeded to another intersection, Route 1009, and turned left, across a bridge spanning the Kentucky River. Once I figured that out, I was deposited into Livingston, a run-down, one-stop-sign town where the road grew wider, acquired a yellow stripe down the middle and, after a few miles, sprouted traffic. I merged south onto US Highway 25, and I knew if I hung on for another half hour, I'd be rewarded with a pot of gold at the junction of routes 25E and 25W.

Kentucky fried chicken
The Colonel Harland Sanders Café and Museum is a must-see.Andrew Cherney

Yep, this is the birthplace of Kentucky Fried Chicken. The original, colorful Sanders Cafe in Corbin is where Harlan Sanders started serving hunks of the fried stuff out of a makeshift kitchen to travelers at his service station. The chicken chunks caught on like wildfire, and the rest is history. A restoration of the original 1940s structure adjoins the functioning cafe, so allow yourself time to peruse the exhibits. The caf serves 21st-century-style fastfood though, which was admittedly more reassuring to my tender Yankee palate than some fried entrees I'd seen advertised during my journey. After filling my belly with grease, I craved more scenery for dessert. Jumping back onto 25W (then State Route 90) delivered me to Cumberland Falls State Park 20 minutes later. The Cumberland Falls are the second-largest waterfalls east of the Mississippi and are known as the Niagara of the South. That's an ambitious description, but the 125-foot-wide curtain of water was an impressive sight nonetheless, especially from the lower trail where I cooled my heels in the wash. Go during a full moon on a clear night, and you'll be rewarded with a rare moonbow -- created when the mist morphs into a multicolored hologram, a phenomenon visible no-where else in the Western Hemisphere. I was intrigued, but since it was late, I rushed back onto 25E to bag the endpoint of the trip.

Cumberland Falls
The Cumberland Falls and Cumberland Gap National Historical Park should both be on your destination checklist.Andrew Cherney

US Highway 25E to the Cumberland Gap National Park was varied enough to keep me alert, though it proved to be heavily trafficked. The Park itself was chock-full of hikes, historical markers and scenic overlooks that I had time to explore only briefly; luckily, the clear day rewarded me with tremendous views across several states from the Pinnacle Overlook. And if you're crossing into Tennessee, there's no better route than the Cumberland Gap tunnel (now a double-bore deal), which burrows under the Appalachians.

Kentucky town
A quaint street in Kentucky.Andrew Cherney

The ride filled the better part of a day, and it could run two days if you took your time. Actual mileage may seem short, but what this loop lacks in distance it makes up for in diversity and nerve. With Lexington as a start/stop point, you can simply jump on Interstate 75 north, after exploring Corbin, to complete the approximately 300-mile loop. There are a few hairy stretches in the ride, but navigating narrow one-laners in tree-shrouded shadows is the thrilling stuff memories are made of. Especially if you manage to find a possum lunch special along the way.