Park at Fred Wiche Park, 7012-22 US 60, Simpsonville, KY   40067, across from Will’s Grill

Miles      Total


Proceed north on Third Street which becomes Todd’s Point Road .3 .3
Right on Antioch Rd 2.6 2.9
Left on Scotts Station 2.7 5.6
Left on Hebron .4 6.0
Left on Anderson 1.2 7.2
Right on Aiken (362) 3.5 10.7
Left on Hanna (1315) 1.6 12.3
Left on Mt Zion Rd (1818) 4.0 16.3
Right on 1408 5.9 22.2
    Stay on 1408 as it twists and turns thru Crestwood
Left on LaGrange in downtown Crestwood  (146) 2.1 24.3
    Exercise caution as you proceed on 146
Left on Maple Ave 1.2 25.5
Right on Old Floydsburg Rd .7 26.2
Left on Ash Ave (362)  .3 26.5
Right on Aiken Rd 3.1 29.6
Left on Flat Rock Rd .3 29.6
Stay left on Flat Rock Rd  at the 4 way intersection 1.1 30.7
    Pass the Long Run Golf Course
Left on Long Run Park Rd .9 31.6
Proceed Left at Fork in Long Run Park Road .2 31.8
Left on Park Road Spur to Long Run Rd 1.3 33.1
Left on Long Run Rd 0 33.1
Right on Aiken Rd   (362) 1.9 35.0
RIght on Webb Rd 2.4 37.4
Left on US 60 5.0 42.4
Left into the Parking Lot of Fred Wiche Park 1.1 43.5

Proceed directly across US 60 to Wills Grill


Summary:  Forty two miles.  Small to moderate hills, start in Simpsonville follow country roads to Crestwood, loop thru Pewee Valley and Long Run Park.   Luke is a competitive cyclist and accomplished photographer who just happens to still be in high school.

Luke’s Long Ride has two personalities.  It is a great individual or small group ride for those who might be feeling their oats. It also offers splendid vistas and stops for those who want to enjoy a leisurely day on a bike. Either way, reward yourself at the finish with southern barbeque from Will’s Grill in Simpsonville.

The Skinny for Those Hammering:

First 20 miles are country roads.  Be very careful to stay single file on hills and curves.    The farm trucks can have very wide mirrors, and there are many blind spots.   Miles 23-26 take you thru Crestwood where you will hit some suburban traffic.  Caution is the word.   The last two miles are on US60, single file is a requirement.

The Detail for Those in to History, Thanks to Bob Hill and Wiki:  


Simpsonville is the Saddlebred Capital of the World.  It was first laid out in 1816 and was named in honor of Captain John Simpson, who represented Shelby County in the Kentucky House of Representatives.  By 1825 it had become a stage coach town, with the Old Stone Inn serving as one of the largest stops between Shelbyville and Louisville.   The Old Stone Inn is still a good stop today.

In 1990 Simpsonville had less than 700 residents.  It is five times that size now, still growing rapidly, and is establishing a town, hence the investment in the Street Scape (sidewalks) which is made possible thanks to the tax income from the Outlet Mall.

Miles 1-15

You cruise by farms, large and small, and a multitude of 5 acre tracks on 15 miles of gently rolling hills.   Cottrells’ Farm Equipment, a family owned store, loves all the business these small spreads generate.   Cotrells’ deserves the business.   They provide excellent customer service.  If you need a chain saw sharpened while you ride, drop it by.

Once upon a time there were sheep on the northeast corner of Todds Point and Antioch.   One spring, before they were sheared, we saw one lying on its back and stopped and watched it struggle for about 5 minutes, but it couldn’t flip over. We hopped the fence and gave it a bit of a push.   A sheep farmer in Ireland later told us that he has to check his flock 3 times a day in the spring, because the sheep will die lying on their backs.


Stonecroft Farm

On Anderson Lane you parallel and then cross Bullskin Creek and immediately start up a hill.   Ride single file on this section of the ride.  Stonecroft Farm on Anderson Lane breeds both horses and dogs.   Established in 1987, it is the only horse farm in the work that has bred both World Champion American Saddlebred and Morgan horses.     Championships have also won at the Westminster Kennel Club Show with Silky Terriers and Cavalier King Charles Spaniels.

Miles 16-30

Hanna Lane is just plain fun to ride and takes you right thru the middle of Taylor Cattle Farm and Harvest Moon Farm.  You cross over Floyds Fork and enter into Oldham County as you intersect Mt Zion Rd which has some good climbs, lots of new sub divisions and Marth’s Pony Farm.     A “Newbie” to Kentucky recently asked who was Floyd?  So much is named after him.  Since we cross Floyd’s Fork several times on this ride, let’s let retired CJ columnist Bob Hill answers that question:

Floyds Fork and John Floyd

Colonel John Floyd was born in Virginia in 1750, worked as a surveyor for a William Preston – as in Preston Highway – and did some other surveying work for a couple of local Virginia guys named Patrick Henry and George Washington.  He married at 18; his wife died a year later at the birth of their daughter, appropriately named “Mourning.”

He first came to what is now Kentucky – then part of Virginia – in 1774 to survey land given to veterans of the French and Indiana War……  It was while on that journey….. the 62-mile river, which begins up in Henry County, was then and there dubbed “Floyd’s River.” It soon became Floyds Fork without an apostrophe - the lack of English teachers in that period quite apparent.


While surveying in this area Floyd bought a 2,000-acre site for himself in what’s now roughly St. Matthews, his land falling between what’s now Breckenridge and Cannon’s Lane extended to DuPont Circle – with Bowman Field thrown in for good measure. There’s a plaque in his honor in the parking lot.


Indian problems – they insisted on continually killing and scalping the white people steadily invading their neighborhood – sent Floyd hustling back to Virginia, a 16-day cross-country journey.

He returned to Kentucky in 1775 and …….lived in Boonesborough in 1776 while the others he left behind on the East Coast got all wrapped up in starting a revolution. He became well-acquainted with Daniel Boone, and even helped rescue his daughter, Jemima, after she was captured by a band of Shawnee and Cherokee Indians.    That same year – he returned to Virginia and got caught up in the Revolutionary War.  He was captured at sea by the British, sent to prison in Portsmouth, England, then escaped to France and eventually Paris in 1777.  From there – with the help of several people including an American ambassador named Benjamin Franklin – he got back to Virginia along with, the story goes, a beautiful pair of shoe buckles and a bright, scarlet-red coat.


He returned to Kentucky in October, 1779 to his reclaim his 2,000 acres of land in Kentucky. After chasing away a few squatters, he established Floyd’s Station along Beargrass Creek with 10 other families about six miles from what’s now downtown Louisville.


In short order he was named one of Louisville’s first trustees, fought Indians with George Rogers Clark, was appointed by Thomas Jefferson as Lieutenant of the Kentucky Militia, became Justice of the Peace and Surveyor of Jefferson County was one of the first two judges appointed in Kentucky….. He was every bit as well-known in his day as George Rogers Clark, Daniel Boone and Thomas Jefferson, with Indian battles still so fierce he wrote a letter home saying the only reasons settlers stayed here was the Ohio River only ran one way.


He was also financially involved with – or at least had great personal interest in – Bullitt’s Lick, a huge salt lick near Shepherdsville that was one of Kentucky’s first major commercial industries. The lick was actually a roughly 100-acre site where salty water bubbled up from the ground. It was placed in big iron kettles and boiled down to pure salt to be used for curing meat, and for human and animal diet.


On April 8, 1783, almost nine years to the day after he first entered Kentucky, Floyd, his brother Charles, Captain Alexander Breckinridge, and several others were traveling south from Louisville to Bullitt’s Lick.  The persistent story goes that Floyd, believing the Indian troubles were behind him, was wearing that bright red coat he’d gotten in France.  Along the Wilderness Road ….. Floyds’ party was ambushed by Indians.


Duncan Memorial Chapel

Turning on to Todd’s Point Road you enter Crestwood and pass Duncan Memorial Chapel.   Located in a beautiful, pastoral setting in Oldham KY, this charming chapel is a favorite site for weddings. Built in 1936 by Alexander Duncan as a memorial to his beloved wife, Flora. The early English Gothic Chapel is built of native stone and is located in one of Kentucky's oldest cemeteries.  Today, Duncan Memorial is one of the most rented wedding venues in the state!


Pewee Valley

Having passed thru Oldham County on Ash Ave you come to the site of present-day Pewee Valley which was first settled as a stop on the Louisville and Frankfort Railroad in 1852 under the name Smith's Station, although it remains unclear which Smith gave his name to the community. It may have been Henry S. Smith, the son of a local pioneer, or Thomas Smith, a local shopkeeper. The name was changed to Pewee Valley on the establishment of a post office by Henry's son Charles Franklin Smith in 1856. The name refers to the eastern wood pewee, a local bird, but, as the town lies on a ridge, the reason for naming the settlement a "valley" remains obscure.

Peewee Valley is home to  the State of Kentucky Correctional Institution for Women (KCIW) which was built in 1938 and until 2010 was on the state owned and operated women’s prison in Kentucky.  The prison continues to house all levels of inmates including all female death row inmates. It has a prison population of about 700.


Long Run Park and the Long Run Massacre

Long Run Park gets its name from the Long Run Massacre which occurred on September  13, 1781 at the intersection of Floyd's Fork Creek with Long Run Creek which is several miles south of the Park. .

A day earlier, settlers at Painted Stone Station about two miles north of the present day Shelbyville,  learned that the fort was about to be raided by a large Indian war party under the command of a  British Captain.   Most of the settlers chose to abandon that station for the better manned ones and left an injured Squire Boone, Daniel’s brother and the Station founder, and one other family behind.   Some settlers hesitated for two days before moving toward Linn's Station.   Following the loss of part of their military guard, the party was ambushed

Despite historical markers and at least one published report indicating that at least 60 people were killed and only a few escaped,  only about 15 settlers were actually killed.  However, 17 soldiers, under the command of none other than  Colonel John Floyd,  were attacked the following day when they went to bury their remains. .  Reenactments are held annually in the Shelbyville, KY area by the Painted Stone Settlers near the site of the massacre.

Webb Road and Dale Place

Dale Place, a two story brick Federal-style home,  at 1809 Webb Road was, built in 1839 by John and Jane Dale. Facing south, it sits back a bit from the road at the end of a gently curving driveway.  It changed ownership several times until the John and Mary Myles bought it in 2003 and have received numerous awards for their restoration

Myles, a Shelby County Family Court judge, is widely known throughout Shelby County for his love of history, and he went to great lengths to ensure that the house, when restored, should be as much as like the original as possible.  When restoring the house, Myles built a large, airy sunroom onto the back of the house, all enclosed in glass walls. He said he placed the room in that manner so that the view into the back yard would be visible even from the front foyer.

US60 and the Lincoln Institute and the Whitney Young Job Corp Center

The Lincoln Institute was an all-black boarding high school in Shelby County, Kentucky, that operated from 1912 to 1966.

The school was created by the trustees of Berea College.  The founders originally intended Lincoln to be a college as well as a high school, but by the 1930s it gave up its junior college function. Lincoln offered both vocational education and standard high school classes. The students produced the school's food on the campus' 444 acres

One notable alumnus of the Lincoln Institute was Whitney Young Jr., a prominent leader of the Civil Rights Movement and director of the National Urban League from 1961 to 1971. Young was born on the campus in 1921. His father, Whitney Young Sr., led the school as its longtime principal.

The rise of integrated education as a result of the Civil Rights Movement reduced the need for general high schools like Lincoln, and in 1966, the Lincoln Institute closed. The campus was used for the Lincoln School for the Gifted, a school for gifted but disadvantaged children, from 1966 to 1970. Since 1972, the old Lincoln campus has been used as the Whitney M. Young Jr. Job Corps Center, a U.S. Department of Labor Job Corps Center. The Center opened in 1972 and provides academic and career training to students on a residential and non-residential basis. The center is administered as part of the Job Corps programs Philadelphia region.[3]

US 60 and the Simpsonville Civil War Massacre Memorial

On the right, just before entering Simpsonville is an Historical Marker  and several rows of crosses  commemorating the massacre of members of the 5th United States Colored Cavalry (USCC) near Simpsonville. On January 25, 1865, Company E of the 5th USCC was transporting a herd of 900 cattle to Louisville. These troops, based at Camp Nelson in Jessamine County, had previously fought at the Battle of Saltville, Virginia. Nearly all of the soldiers were former slaves.

When the troopers neared Simpsonville, they were attacked by Confederate guerrillas. During the fight, which the Louisville Journal called “a horrible butchery,” twenty-two of the USCC were killed and eight were severely wounded. At least four of the injured later died from their wounds.

The dead Union soldiers were buried in a mass grave and the area eventually became an African-American cemetery. Today, the graves marked to commemorate the soldiers killed in the ambush.