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Cycling through Kentucky history 

MOST EARLY SETTLERS made their way into Kentucky on two rustic roads—the Boone Trace through Cumberland Gap and the Limestone Trace down from the Ohio River. Now you can see some of what those pioneers saw by riding your bicycle on a beautiful, challenging route of more than 250 miles through 10 counties between Middlesboro and Maysville. 

This is part of U.S. Bicycle Route 21, which runs 1,044 miles between Atlanta and Cleveland. The Kentucky section was created in 2019 and well-marked with signs in 2021. Free smartphone GPS navigation maps, northbound and southbound, can be downloaded from the Adventure Cycling Association. 

This bicycle route grew out of an effort by the nonprofit organization Friends of Boone Trace to identify and protect remnants of the path Daniel Boone and a crew of about 30 men blazed through Cumberland Gap to Fort Boonesborough 250 years ago this spring. 

“We wanted to preserve what segments are left of Boone Trace and raise awareness about how important this little road was to the growth and development of our country,” says John M. Fox, a Lexington physician who helped start Friends of Boone Trace. 

To reach the Kentucky River bank where they built Fort Boonesborough, the men took advantage of mountain gaps, streams and ancient paths used 

by Native Americans and buffalo herds. Much of Boone Trace was later incorporated into 19th century roads and railroad lines and 20th century highways. 

To avoid busy highways when possible, the bicycle route’s planners used forgotten sections of the original trails and lightly traveled parallel roads. Kentucky cyclists are fortunate, because even most rural roads are well-paved. But this route includes some stretches of rough asphalt and about 4 miles of gravel road. It is well-marked throughout, and on the Boone Trace section, tape on the pole just below the sign tells you whether you are on the original Boone Trace (green), near it (blue) or away from it (white). 

This trip will be most enjoyable for fit, experienced cyclists. Choose a bike with plenty of hill-climbing gears and tires at least 32 millimeters (1.26 inches) wide. A gravel bike is ideal, although a suitably equipped road or hybrid bike will work. A mountain bike will, too, although you will work harder on the gently rolling, well-paved roads that make up most of this route. 

Unless you love bikepacking, the best way to do a multiday ride like this is to have a support vehicle haul your overnight bag to each stop. If that’s not possible, travel light with essentials in bike bags or a small backpack. 

Nathan Rome of Kentucky Cycling, whose website has an excellent four-video guide to this route, rode it with friends over four days. But I would suggest a more leisurely five-day trip. 

Middlesboro to Barbourville 

In the spirit of Daniel Boone, begin at Cumberland Gap National Historical Park near where Kentucky, Tennessee and Virginia meet. Before you start, tour the visitor center for historical context and drive up to Pinnacle Overlook for a bird’s-eye view of the Gap. 

From the visitor center, ride a few blocks through Middlesboro before scenic backroads lead you through Bell County to Pineville. There are short sections on U.S. Highway 119, which has a narrow shoulder and rumble strip, and U.S. Highway 25 E., which is busy but has a wide shoulder. They are the first of many short stretches on busy roads, so be careful. 

Soon after entering Knox County, you pass through Flat Lick, where three historic trails converged: Boone Trace, the Wilderness Road branch to Harrodsburg and Warrior’s Path, an ancient Native American trail. Take a break and read the historical markers, then proceed to Barbourville for the night. Your first day’s ride is only about 40 miles, but it is a good warmup that will leave you fresh for the next day’s hills and gravel. 

Barbourville to Mount Vernon 

Soon after leaving Barbourville, you come to two 1-mile stretches of flat gravel roads along a railroad line. A long climb takes you into Laurel County, one of the hilliest parts of this route. 

Take a break at Levi Jackson Wilderness Road Park to see the collection of antique millstones. The next break comes after you enter Rockcastle County, where there are several miles of flat, beautiful road beside the Rockcastle River that take you into Mount Vernon. You’ll sleep well there after this hilly, 70-mile day. 

Levi Jackson Wilderness Road Park is named for an early Laurel County settler. Photo: Tom Eblen
A small park with monuments in Flat Lick in Knox County marks the intersection of three early Kentucky roads. Photo: Tom Eblen
At the beginning or end of U.S. Bicycle Route 21, visit Cumberland Gap's Pinnacle Overlook. Photo: Tom Eblen
Boone Tavern in Berea offers fine dining and accommodations for visitors. Photo: Tom Eblen
Thatchers Mill Road in North Middlettown comprises a section of U.S. Bicycle Route 21. Photo: Tim Webb

Mount Vernon to Winchester

Begin your third day with a tour of The Kentucky Music Hall of Fame and Museum at Renfro Valley, a famous country music show venue since 1939. 

Then comes a hilly 2-mile section of gravel road. As you enter Madison County, you come to Boone Gap, where knobby hills give way to the Bluegrass plateau. 

The next stop is Berea, home of Berea College, the first interracial, coeducational college in the South. There is fine dining at Boone Tavern, as well as restaurants and Appalachian craft shops nearby. The John Stephenson Trail takes you to backroads around Berea and on to Richmond. After a busy stretch crossing over Interstate 75, you pass Eastern Kentucky University’s campus and ride through downtown. 

From Richmond, it is a hilly ride along the last stretch of Boone Trace to Fort Boonesborough State Park. There are historical markers at the fort’s site beside the park campground. It’s worth a ride or hike up the hill to a 1974 reconstruction of the fort. On the weekend of Sept. 14–15, the siege of Boonesborough will be commemorated with a re-enactment of a 1778 battle in which Boonesborough’s inhabitants successfully fought off a larger force of Shawnee warriors and British troops. 

The ride from Boonesborough to Winchester begins with a steep climb up State Route 627. But ignore the official route here and, as you begin the climb, turn right onto Old Boonesborough Road. It runs parallel to State Route 627, then crosses it at the top of the hill and runs along the left. It is more pleasant than fighting busy highway traffic. It also takes you through Forest Grove, where Beech Springs Farm Market sells delicious fried fruit pies. Stay overnight in Winchester. 

Winchester to Blue Licks

Between Winchester and Millersburg, you ride on one great cycling road after another. Millersburg’s Main Street was once part of Limestone Trace, which over the years was widened, straightened and bypassed into modern U.S. Highway 68. To avoid traffic, the bicycle route after Millersburg winds north on hilly, rough roads in Nicholas and Robertson counties. 

After two 70-mile days, today’s journey is only about 40 miles. Before checking into the Blue Licks Battlefield State Resort Park lodge for the night, visit the Pioneer Museum. It tells the story of the Battle of Blue Licks in 1782, one of the last battles of the American Revolution. About 350 Native American warriors and British loyalists ambushed Daniel Boone and 180 other settlers, who had traveled there to collect salt. 

The settlers suffered 100 casualties, including Boone’s son, Israel. 

Blue Licks to Maysville 

Mason County is the last of the 10 counties you ride through, and it has challenging hills. Stop in Washington, a once-thriving town established in 1786 that retains many historic buildings as shops and restaurants. Then comes a long descent into Maysville. Your last day’s ride is not quite 40 miles, leaving plenty of time to tour this historic Ohio River town. 

Stop by the Kentucky Gateway Museum Center, an outstanding local history museum that has a world-class exhibit of building miniatures. Next door, sample bourbons from Old Pogue Distillery, founded in 1876 and now operated by the fifth and sixth generations of the Pogue family. 

U.S. Bicycle Route 21 covers a lot of history and beautiful scenery. It makes you realize why so many settlers were eager to start new lives in Kentucky more than two centuries ago.

Map and preview of U.S. Bicycle Route 21 

At 250-plus miles, this trip requires some navigation assistance. The Adventure Cycling Association offers free smartphone GPS navigation maps, northbound and southbound, on its website

The Kentucky Cycling website, created by Nathan Rome of Frankfort, is a great source of cycling information, including more than 220 videos of rides in 82 counties. The site also has maps and other practical information. 

TOM EBLEN is a former managing editor and columnist at the Lexington Herald- Leader. He has ridden bicycles more than 33,000 miles since 1995. 

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