Plan a history drive
Kentucky history drives
12 themed drives across the state and 12 loops that start at 10 Kentucky distilleries. Each page lists the stops in order, with a route map, stories and directions.
Build your own drive
Pick a town, a distillery or your location and the time you have, from 1 hour to a full day; we suggest a loop of nearby stops.
Covered bridges
Civil War
Frontier and pioneers
Bourbon and distilleries
Capital and museums
Caves
Rail and transport
Native nations
Themed drives
- Covered bridgesThemed drive
Licking Valley: Stations, Blue Licks and Covered Bridges
From the 1780 raids on Ruddell's and Martin's stations to the 1782 Battle of Blue Licks, with three covered bridges, ending in old Washington.
7 stopsAbout 89 miAbout 2 h 33 min driving
- Civil WarThemed drive
Big Sandy and Pine Mountain
From Pound Gap on Pine Mountain down the Big Sandy valley: Pikeville's heritage center, the 1861–62 battles at Ivy Mountain and Middle Creek, Jenny Wiley's story and a mountain farm community.
6 stopsAbout 92 miAbout 2 h 04 min driving
- Frontier and pioneersThemed drive
Bluegrass Forts and Stations
From James Harrod's 1774 settlement to the springs where Lexington was named, then east to the stations near Winchester and Boonesborough that settlers held through the raids of 1779–1782.
5 stopsAbout 70 miAbout 1 h 38 min driving
- Frontier and pioneersThemed drive
Boone's Trail and the Wilderness Road
From Cumberland Gap, where Thomas Walker followed an Indian road in 1750, north along the settlers' route to Logan's and Whitley's stations and Boone's fort on the Kentucky River, then east to Pilot Knob, by tradition where Boone's party first looked out over Kentucky in 1769.
6 stopsAbout 185 miAbout 4 h 10 min driving
- Bourbon and distilleriesThemed drive
Bourbon Heritage: the family distillers of the Rolling Fork country
Out from Bardstown into the Nelson, Washington and Marion county hollows: the Willett farm, Henry McKenna's Fairfield, Jacob Beam's Hardin's Creek and a Beam descendant's distillery at Lebanon.
4 stopsAbout 56 miAbout 1 h 25 min driving
- Capital and museumsThemed drive
Capital, Shakers and the Early Commonwealth
From the Old State Capitol and Liberty Hall in Frankfort to the Glenn's Creek distillery, the Shakers of Pleasant Hill, and Danville's square where Kentucky's statehood conventions met.
5 stopsAbout 60 miAbout 1 h 40 min driving
- CavesThemed drive
Cave Country
From Bowling Green's Lost River Cave to Mammoth Cave and Horse Cave: the karst country where saltpetre was mined for the War of 1812 and show caves drew paying visitors from 1816 on.
5 stopsAbout 52 miAbout 1 h 23 min driving
- Civil WarThemed drive
Civil War in the Bluegrass
From Kentucky's largest Civil War battle at Perryville to the Union recruiting camps at Camp Dick Robinson and Camp Nelson, the 1862 fight at Richmond, and the Lexington home of the Hunt and Morgan families.
5 stopsAbout 104 miAbout 2 h 33 min driving
- Civil WarThemed drive
Civil War in South Central Kentucky
From the January 1862 Union victory at Mill Springs to Morgan's 1863 raid at Tebbs Bend and Lebanon, then the fights for the Green River bridge and Glasgow's fort.
6 stopsAbout 157 miAbout 3 h 36 min driving
- Rail and transportThemed drive
Northern Kentucky: Ice Age to the Roebling Bridge
From the Ice Age salt springs at Big Bone Lick through Boone County's seat and a Dinsmore farm to the 1862 defenses of Cincinnati and Roebling's bridge.
5 stopsAbout 42 miAbout 1 h 26 min driving
- Civil WarThemed drive
Pennyrile Towns and Civil War Memory
Pennyrile county seats from about 1800, the camp meeting that started the Great Revival, a divided state's Civil War memory at Fairview, and an eight-sided house near Franklin.
5 stopsAbout 71 miAbout 1 h 45 min driving
- Native nationsThemed drive
Western Rivers: Mississippian Towns, Clark's Fort and the Trail of Tears
Along the lower Ohio and Mississippi: the Cherokee Trail of Tears at Mantle Rock, Civil War Paducah, the Mississippian town at Wickliffe, Clark's 1780 fort and the Confederate river fort at Columbus.
5 stopsAbout 90 miAbout 2 h 16 min driving
Start at a distillery: 10 distilleries, 12 loops
- Bourbon and distilleriesDistillery start
Barton 1792: Bardstown and the Catholic Holy Land
Loop 1: Bardstown to Loretto
Starting at Barton 1792 on the edge of Bardstown: Spalding Hall, Federal Hill, and the Holy Cross and Loretto country to the south.
5 stopsAbout 46 miAbout 1 h 28 min driving round trip
- Bourbon and distilleriesDistillery start
Buffalo Trace · Loop 1: Capital and the river
Frankfort history near the distillery
Starting at Buffalo Trace on the Kentucky River at Frankfort: where Leestown stood, the capital that grew beside it, and the Glenn's Creek distilleries a few miles south.
9 stopsAbout 28 miAbout 0 h 55 min driving round trip
- Bourbon and distilleriesDistillery start
Buffalo Trace · Loop 2: Glenn's Creek distilleries
Frankfort history near the distillery
Starting at Buffalo Trace on the Kentucky River at Frankfort: where Leestown stood, the capital that grew beside it, and the Glenn's Creek distilleries a few miles south.
4 stopsAbout 27 miAbout 0 h 56 min driving round trip
- Bourbon and distilleriesDistillery start
Castle & Key: Glenn's Creek to the capital
Loop 1: Frankfort museums and the Elkhorn
Starting at Castle & Key on Glenn's Creek: the State Arsenal, the Kentucky Historical Society, Daniel Boone's grave and the Switzer covered bridge.
5 stopsAbout 30 miAbout 1 h 03 min driving round trip
- Bourbon and distilleriesDistillery start
Four Roses: Lawrenceburg and the Salt River settlements
Loop 1: McAfee country and Fort Harrod
Starting at Four Roses on the Salt River: Lawrenceburg's beginnings, the McAfee settlers of 1779, and James Harrod's 1774 town.
4 stopsAbout 46 miAbout 1 h 04 min driving round trip
- Bourbon and distilleriesDistillery start
Heaven Hill: Bardstown and the road to Lincoln's birthplace
Loop 1: Bardstown, New Haven and Lincoln's birthplace
Starting at Heaven Hill in Bardstown: the town's founding, Federal Hill, Spalding Hall and Union Church, then south to the Kentucky Railway Museum and Lincoln's birthplace.
8 stopsAbout 63 miAbout 1 h 44 min driving round trip
- Bourbon and distilleriesDistillery start
Jim Beam: Clermont, Salt River salt and Civil War forts
Loop 1: Salt River and Fort Duffield
Starting at Jim Beam in Clermont: the Bullitt's Lick salt works, the Salt River falls at Shepherdsville, and a Union fort above West Point.
5 stopsAbout 56 miAbout 1 h 35 min driving round trip
- Bourbon and distilleriesDistillery start
Maker's Mark: Loretto, Holy Cross and the Lincoln country
Loop 1: Holy Cross, Lebanon and Springfield
Starting at Maker's Mark in Loretto: the Maryland Catholic settlement at Holy Cross, Civil War Lebanon, and the Springfield courthouse and homestead tied to Abraham Lincoln's parents.
6 stopsAbout 57 miAbout 1 h 45 min driving round trip
- Bourbon and distilleriesDistillery start
Old Forester: Whiskey Row to Cave Hill
Loop 1: Whiskey Row to Zachary Taylor
Starting at Old Forester on Louisville's Main Street: the riverfront distillers, the Filson, Cave Hill, and the Speed and Croghan homes.
9 stopsAbout 32 miAbout 1 h 13 min driving round trip
- Bourbon and distilleriesDistillery start
Wild Turkey · Loop 1: Tyrone, Versailles and Jack Jouett
Tyrone, Versailles and the Kentucky River
Starting at Wild Turkey above the Kentucky River: the Tyrone distilling past, Versailles and Jack Jouett, and the Shakers of Pleasant Hill.
4 stopsAbout 28 miAbout 0 h 59 min driving round trip
- Bourbon and distilleriesDistillery start
Wild Turkey · Loop 2: Shaker Village of Pleasant Hill
Tyrone, Versailles and the Kentucky River
Starting at Wild Turkey above the Kentucky River: the Tyrone distilling past, Versailles and Jack Jouett, and the Shakers of Pleasant Hill.
3 stopsAbout 58 miAbout 1 h 21 min driving round trip
- Bourbon and distilleriesDistillery start
Woodford Reserve: Glenn's Creek, Versailles and Midway
Loop 1: Versailles and Midway
Starting at Woodford Reserve on Glenn's Creek: Versailles, Jack Jouett's house, Midway's mill and cemetery, and Woodford County's rail history.
6 stopsAbout 40 miAbout 1 h 23 min driving round trip
Miles and times are estimates from OpenStreetMap routing, not live traffic. Archaeological sites are shown at approximate locations, and private-land sites are marker only, with no directions.