A Kentucky railroad depot and dirt road in the early twentieth century

Local History

Quantrill's Trail

A chapter of regional history, gathered from records, letters, and local memory.

Historic Bradfordsville storefront

William Clark Quantrill and his guerillas, on their way east to Maryland, masqueraded as Union Soldiers. Quantrill and his men traveled from New Market, near Lebanon to Hustonville, near Danville by way of Bradfordsville where they burned and ravaged several homes and businesses.  William Clarke Quintrell was born Dover, OH -  July 31, 1837 to Thomas H. Quantrill and Caroline C. Clark.  He died in Louisville, KY - June 6, 1865 at the age 27.  He is buried in the Confederate Memorial State Historic Site, Higginsville, MO. See Wikipedia article: https://en.wikipedia.org/wiki/William_Quantrill regarding burial.

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  1. Map Marker 1a

    Lebanon National Cemetery

    Many Civil War graves can be found here.

  2. #*Map Marker 1

    New Market 

    On February 8, 1865, Quantrill who had previously been here on January 28, 1865, killed four Union Scouts and destroyed a wagon train. Four men were captured by Quantrill and taken to Bradfordsville and killed.

  3. +Map Marker 2

    Liberty Meeting House 

    A meeting was held in 1789 in Bradfordsville concerning the need to build a Presbyterian church. The group decided to build on Hardin's Creek, which is now Lebanon. Transportation in those days was so rugged that the Presbyterians decided to build another church in 1813 at this location and name it Liberty Meeting House. A cemetery was started next to the church, it grew as more land was donated to the grave site. Slave and their masters worshiped together in this church, both are buried in this cemetery.

  4. *Map Marker 3

    Toll Gate Encounter

    This site, which was a former Toll Gate for the collection of fees to use this road, was the site of a battle between Quantrill's guerillas and Major Mahoney's Union troops on February 8, 1865. Four Union men captured in New Market were killed on this lot. Sue Mundy, who helped Quantrill had his horse killed here.  The horse fell on Mundy and only with Quantrill's help was he able to get free. Several people were killed were injured and killed on this site.

  5. +Map Marker 4

    Home College

    An accredited college that taught the finer aspects of life - as the academy was noted for - was charactered by the Commonwealth of Kentucky in 1866. It closed circa 1900. Bricks that came from this structure were used to construct the Rolling Fork Bank.  Located where the Drye Park is presently, in 1902.

  6. +Map Marker 5

    Old Bradford House

    An old log house was build by Adam Bradford, the family for which Bradfordsville was named, around 1810. A new house which could be seen across the North Rolling Fork River was constructed in 1866. This may have been due to the burning by Quantrill as he came through Bradfordsville.

  7. *Map Marker 6

    Burning of Bradfordsville

    Quantrill and his guerillas came up Main Street, which is River View Drive at the present, looting and burning as they traveled. A watchman rang the bell at the Yowell Hotel to warn the citizens of Bradfordsville. Quantrill burned the hotel, Liberty Stable, and tavern in revenge for the warning.

  8. *Map Marker 7

    Doctor John Fleece

    Dr. Fleece was attending a patient at her home, which is the present home of Mrs. Linnie Raney, when on February 8, 1865, Quantrill's guerillas stole the Doctor's fine horse and left him a nag.

  9. +Map Marker 8

    Fort Kennet

    Facing the grassing hill you see the site that held a Fort built between 1770 and 1800.  This was the site where Alexander Coppage led a hunting party at night and was attacked by Indians. Coppage was scalped, but lived several years after this.

  10. *Map Marker 9

    Doctor Joseph Rose

    This gentleman helped to plan the design of Bradfordsville; he was also the first Doctor here. His brick home was burned by Quantrill on his February 8, 1865 pillage of Bradfordsville. Near the house is the Rose cemetery. Uriah M. Rose, the son of Dr. Rose, went to Arkansas and founded the Rose Law Firm. None of the Rose family is presently in the Law Firm. Uriah was consolate to the Hague under Teddy Roosevelt; his statue is in the Statuary Hall in Washington D.C.

  11. +Map Marker 10

    Doctor William Perry Rose

    Dr. Rose was summoned by the Union Army to treat the wounded at Chelf House. He being deaf didn't here the order to halt when the Union Army gave command. The Union shot him in an ironic twist as he came to aid them October 13, 1863. The Chelf House, a spacious house built in 1832 by Elias Chelf and family. He had a carding business and flour mill, in 1852 he began using steam to power his flour mill. There was once five slave cabins in the rear of the home. The rock wall in front of the home was erected by slaves.  During the Civil War this home served as a field hospital.  This home is now the residence of Evelyn Purdy.

  12. +Map Marker 11

    Big Bend

    The Union Pay Master was on his way to pay soldiers near the Jacktown area. In this curve of the South Rolling Fork River he was robbed of his payroll. The all gold payroll was later found in Crab Orchard.

  13. *Map Marker 12

    The Prewitt House

    Prior Prewitt was shot February 8, 1865 through his front door by Quantrill and his guerillas because he refused to open his door. The bullet hole can still be seen at present day.  Prior's brother-in-Law, William Cunningham, lived on the next farm. As William tried to protect his horses from the stealing guerillas, he was shot. The guerillas of Quantrill were so ruthless that they ran the stolen horses over the dead body of William.

  14. *Map Marker 13

    Battle at George Mill's Home

    Quantrill, who was trying to locate his enemy Captain Bridgewater mistakenly located the home of Colonel Wolford. No one was at home, so Quantrill went to the next house which was George Mill's home. Here Quantrill demanded food and shelter. Capt. Bridewater, who was in pursuit of Quantrill, located Quantrill at about 2 a.m. The Quantrill guerillas panicked and ran bare footed through the hills and woods toward Parksville and Haysville. Four of the guerillas were buried across the fence of a present day Amish family. One straggler was killed and buried on Hocker Knob February 8, 1865.

  15. #Map Marker 14

    George Drye Home

    Quantrill and his men, dressed in Union uniforms in an attempt to pass as Union Soldiers.  They spent the night of January 28, 1865 at George Drye's home in Bradfordsville, Major George Drye was there at the time. The next day, the guerillas rode away on Col. Frank Wolford's and Maj. George Drye's fine prized horses.

  16. #Map Marker 15

    Hustonville Hotel

    Quantrill killed George Frank Cunningham when he refused to part with his mare at this location on January 29, 1865. All of the horses there were stolen and Quantrill and his guerilla's headed toward Danville. Quantrill's maneuvers were so successful at this location that he returned to the Bradfordsville area on February 8, 1865 to acquire more horses and possibly some support. Finding that this was not as he expected, he killed and burned much that he found.

# Quantrill activity Jan. 1865.  * Quantrill activity Feb. 1865.  + Other area historic sites.

Map markers are approximate. Map for entertainment purposes only.

Illustrated view of the events along Quantrill's Trail
Click here to download map.

It is important to know that William Clarke Quantrill was neither a Union nor Confederate Soldier. He leaned more toward the Confederacy but was more renegade, trying to do as he saw fit, and seemed to almost enjoy destroying and killing as he led his cause. Quantrill was accompanied by several men we call guerillas, which had included Sue Mundy, and Frank and Jessie James.  Although his exploits were feared and fought by those on either side of the Civil War, especially those who leaned toward the Union side, as did much of this Central Kentucky area.

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