Ale-8-One is a ginger-ale-like soda usually sold in glass bottles and popular in the hills of eastern Kentucky. During a bike trip through the region last month, for example, I washed down a burger with one on the back porch of a bed-and-breakfast owned by a man who once walked more than 3,000 miles across America on stilts. The next night, I blasted another out of the crook of a tree branch with a 9-millimeter Smith & Wesson.
I rarely drink soda and I’m not into guns. But what’s the point of travel if not to have new and sometimes discomforting experiences?
Eastern Kentucky, Appalachian coal country, was, in truth, a rather random destination, the result of browsing the routes plied by Megabus and realizing I could get to nearby Lexington from New York for only $63, round trip. (Warning: the bus trip is far from direct and took me a total of 17 hours on the road, with two connections.) As my method of transit within the state, I chose a bicycle. Bikes are the most social form of of transportation; people wave to you, and you can stop in anywhere to fill a water bottle or charge a phone. Though Kentucky has plenty of beautiful scenery, my hope was that this trip would be about people. Bring on the discomfort.
After some emails and phone calls with two avid Lexington cyclists — Randy Thomas, president of the Bluegrass Cycling Club, and Allen Kirkwood of the nonprofit Broke Spoke Community Bike Shop — I had a four-day, 160-mile back roads route through a bit of bluegrass country, best known for its horses and bourbon, and then east into the hills. I would pass by Red River Gorge in Daniel Boone National Forest, and tiny towns with nary a restaurant or motel before picking up about 20 miles of a new bike and horse path, the Dawkins Line Rail Trail. It ends near a small town called Paintsville, which happens to be home to a rare Enterprise Rent-a-Car office that could get me back to Lexington and my return bus.
But first, the bike. At Scheller’s Fitness and Cycling in Lexington, a Trek Domane 4.3 was $160 for up to a week. Once I had wended my way out of the city, things got scenic fast: car-free country lanes lined with deep-brown, four-rail fences enclosing lush pastures dotted with horses that barely moved in the heat. It felt like riding through a painting, until a horse’s tail whisked away a fly or a wind gust rustled a tree.
A couple of hours in, things began to change. Horses gave way to cows, fences got shabbier, the paint on homes more weathered. And I finally began to encounter people, as in the tiny, worn center of North Middletown, population 650 or so, where I stopped at a gas station and convenience store that was — typically, I would later learn — the lone source of action in town. I treated myself to a soft ice cream ($1.69) and asked a man sitting outside what was going on. “Nothing,” he said. “People are either on welfare or on drugs.”
Back on my bike, I headed through a route dotted with barns. Slender gaps in the boards of one older barn created a strobe effect as I rode past. Outside another, dozens of goats lounged in the shade, only to scatter as I approached, as had horses earlier in the trip.
Thirty-odd miles later, after an unfussy $9.99 catfish dinner at Kathy’s Country Kitchen in Clay City, I checked into the nondescript Abner Motel ($60 for the night), expecting to collapse on my bed. However, Mexican ranchera music was playing in the parking lot and I wandered out to inquire. A mostly Latino group of workers on a local gas pipeline was occupying a row of rooms, and had set up a barbecue.
A Texas-born Mexican-American gave me a Corona and pointed me toward the grill; Salvadoran immigrants from Tallahassee, Fla., talked about the time they had worked on a Nantucket golf course where Bill Clinton played; and a burly West Virginia ironworker named Jim urged me to try his co-worker’s freshly made salsa. Jim also tried to give me a tutorial on the use of white bread as a leak-stopper for cracked PVC pipe. Ah, people. So much more welcoming than horses or goats.
With a lack of lodging along upcoming stretches of my route, I was to stay the next night just six miles ahead (plus the loop through the national forest), at a bed-and-breakfast. At $110, it was way over my budget, but Randy and Allen, the two bike experts, insisted that I was not to miss the character who owned it: Joe Bowen, a retired construction worker, political activist, inveterate storyteller and Kentucky booster. His local bona fides were strong, to wit, his Bowen Farm Bed & Breakfast is at 315 Bowen Road, in Bowen, Ky., and his family has been in the region since the 1700s. A widower, he built the house using parts he had salvaged in the demolition of old country estates.
Joe had extraordinary energy. He made the beds, cooked breakfast, booked reservations and entertained his guests, which in this case meant me and the six-person Olnick family, who had been vacationing at Joe’s for years. Randy and Allen had told him about me, so my cover had been blown, and I thought I might be given special treatment. It was his regulars who got it.
In just the day I was there, he repeatedly pushed the youngest Olnick, Addison, on a swing and held a barbecue and joint birthday party for himself (he turned 72) and the Olnick’s oldest daughter, Kearstin (14). (This was where I tried the Ale-8-One.) They treated Joe like a grandfather, and he spoiled them as though he was one.
That day, after I had biked into some challenging hills in the Red River Gorge Geological Area, Joe met me in his truck (with two of the Olnick kids in tow) to show me some views of the forested gorge and its sandstone cliffs, popular among climbers. These included views of two of the 100-plus natural bridges the area is perhaps best known for. I questioned whether Joe would do this for all his guests, but the stories he told at Sky Bridge and Angel Windows were so smooth and practiced it was obvious I was far from the first to hear them.
In fact, his stories never stopped. How he had maneuvered to have the founder of a local children’s home carry the Olympic torch. How he had walked from Los Angeles to Bowen on stilts, and later traveled across the country by bike. How he got a statue built of his favorite Kentucky leader, Bert Combs, who was governor from 1959 to 1963. And then there was the time he made the newspaper, by accusing a prominent architect of stealing ideas for a building in downtown Lexington from the Sphinx.
I’d miss all this hospitality during the following two-day stretch of my trip, with 85 miles to Paintsville and nowhere to sleep in between.
I started again early Sunday morning, riding past barns decorated with colorful quilt patterns, flower-covered graves in tiny family cemeteries, Civil War plaques (Kentucky was a famously divided border state), and, occasionally, shops that could have passed for tourist attractions, like Bea’s Bee Hive in Hazel Green, a former general store turned into something between a yard sale and an antiques shop, open only on weekends.
What were really missing were lunch options, which were limited mostly to Hunt Brothers Pizza at gas stations. That problem was solved at the tiny, whitewashed Country Side Community Church along a meandering stretch of Route 134. I was attracted by the “Everyone welcome” sign, handwritten on blistered white paint, and headed in, hoping to have a glimpse inside, a friendly conversation or, who knows, a lead on a place to sleep. Instead I found a meal — there was plenty of spaghetti and meat sauce in the kitchen left over from play rehearsal for an upcoming bible camp — heard from the family that had so kindly invited me in about how the church was founded by a missionary from New York, and admired their “tarpin,” which is how they pronounced terrapin.
By 5:30 or so, I had reached the Dawkins Line Rail Trail, but I found it was gravel and not bike-friendly. Wondering about a potential alternative route, I stopped at yet another gas station, the Parkway Convenient Mart, for some assistance.
This one was different. At the counter, homemade Kentucky cream candy (a melt-in-your-mouth local treat) was on sale in plastic baggies for $3, and people gathered by an out-of-place communal table near the soda machine. They were members of the Marsillett family, owners of the store. The road would take me to Paintsville, they said, but they doubted I could make it there before dark.
So they made me an offer: I could stay in one of the family’s hunting cabins, set deep in the woods amid their hundreds of acres. Minutes later I was hanging out with Kevin, 19, and his cousins, Cody, 14, and Jordan, 10, at their pool. The family was obviously well-off, at least in local terms: The house was huge, and in addition to owning the gas station, the family bred hunting dogs and owned a metal scrapyard. And raised goats, who stared down at us from a small bluff as we dropped down the water slide.
Kevin, Cody and Jordan seemed to be tickled by the presence of an urban guest; they showed me the house’s “man-cave” (a sign labeled it as such), where camouflage furniture prevailed and hunting trophies covered the walls. Cody told me they had once adopted a sick bobcat. “You’re the first family I’ve ever met to have a bobcat,” I told him.
He corrected me: “We’ve had two.”
The boys took me to two safes in the master bedroom, where the family’s huge gun collection was stored. The arsenal included collector’s items like an intriguing double-barrel shotgun with a separate trigger for each barrel and a pink gun, “for Mom.”
We jolted up an impossibly rutted, rock-filled hill in the family’s side-by-side ATV, with Cody at the wheel. Nobody but me buckled his seatbelt. The cabin, really a Lowe’s tool shed with pieces cut out and windows installed, was perched on a platform high off the ground, deep in the woods. Night was falling.
“This would be a good place to kill someone,” said Kevin, and then looked to see if he had scared me. Inside was a cot, a stove and a half-dozen buzzing wasp nests. Cody burned them with a stove lighter and killed any escapees with his baseball hat.
Later that night, after a pizza from the gas station, we headed back to the cabin for the evening’s activity: target practice. They placed an Ale-8-One bottle horizontally in the nook of a tree, and handed over the Smith & Wesson pistol. (I should note here that I have used guns before and know the basics, so this was not as insane as it sounds.) Bam! I knocked off the whole bottom of the bottle with the first shot, though the top stayed put and I proceeded to miss it entirely, six shots in a row.
The night was calm, except for a sting from a half-dead wasp that I missed on the cot. I thanked everyone the next morning and took the road into the hills, reaching Paintsville by about 11 a.m. It turned out I could have made it the night before, but I was glad I hadn’t tried. My motel in Paintsville was quiet and anonymous. The Marsillett family experience had been anything but.
A version of this article appears in print on July 12, 2015, on page TR8 of the New York edition with the headline: Open Doors Along Back Roads.