Upcoming Races Near Winchester, KY

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2026 Juneteenth Freedom 5K

Richmond, KY

Saturday, June 20th, 2026

1 Mile

View details for race 2026 Juneteenth Freedom 5K

Run The Runway 5K

Danville, KY

Saturday, June 20th, 2026

View details for race Run The Runway 5K

North Lime Donut Dash 3K

Lexington, KY

Saturday, June 20th, 2026

View details for race North Lime Donut Dash 3K

Eckert's Versailles Orchard Donut Dash 5k

Versailles, KY

Sunday, June 21st, 2026

View details for race Eckert's Versailles Orchard Donut Dash 5k

The Ascent Red River Gorge 5K & 10K Trail Races

Slade, KY

Saturday, June 27th, 2026

10K

Trail

View details for race The Ascent Red River Gorge 5K & 10K Trail Races

Stars, Stripes & Strides 5K

Versailles, KY

Saturday, June 27th, 2026

View details for race Stars, Stripes & Strides 5K

RJ Corman 5K Run

Wilmore, KY

Saturday, June 27th, 2026

View details for race RJ Corman 5K Run

6th Annual Run Morehead 5K

Morehead, KY

Friday, July 3rd, 2026

View details for race 6th Annual Run Morehead 5K

Bluegrass 10,000

Lexington, KY

Saturday, July 4th, 2026

10K

1 Mile

View details for race Bluegrass 10,000

Blackberry Festival 5K

Carlisle, KY

Saturday, July 4th, 2026

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Beat the Heat 5K

Lexington, KY

Saturday, July 11th, 2026

View details for race Beat the Heat 5K

Eagle 5K, 10K & 13.1M at Richmond, KY (28)

Richmond, KY

Saturday, July 11th, 2026

10K

Half

View details for race Eagle 5K, 10K & 13.1M at Richmond, KY (28)

Run Wild Rhino Rush 5k

Georgetown, KY

Saturday, July 11th, 2026

Fast

View details for race Run Wild Rhino Rush 5k

Roots of Mercer 5K & 1 Mile Fun Run

Harrodsburg, KY

Saturday, July 11th, 2026

1 Mile

View details for race Roots of Mercer 5K & 1 Mile Fun Run

Crank & Boom Sprint For Scoops 3K & Kid's Dash

Lexington, KY

Friday, July 17th, 2026

View details for race Crank & Boom Sprint For Scoops 3K & Kid's Dash

Survive the Night Relays

Lexington, KY

Saturday, July 18th, 2026

Marathon

Ultra

Trail

View details for race Survive the Night Relays

Bagel Boogie 2 Miler & FREE Kid's Dash

Berea, KY

Sunday, July 19th, 2026

Trail

Fast

View details for race Bagel Boogie 2 Miler & FREE Kid's Dash

Trail Camp for Big Kids

Robinsville, NC

Thursday, July 23rd, 2026

Marathon

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Moonlit Mile 5K

Richmond, KY

Friday, July 24th, 2026

1 Mile

View details for race Moonlit Mile 5K

Distillery Dash Cross Country 5k/10k

Lexington, KY

Friday, July 24th, 2026

10K

View details for race Distillery Dash Cross Country 5k/10k

Run White & Blue 5K & 10K

Lexington, KY

Saturday, July 25th, 2026

10K

1 Mile

Fast

View details for race Run White & Blue 5K & 10K

#FEEDTHEKIDS Beer Mile

Lexington, KY

Saturday, July 25th, 2026

1 Mile

View details for race #FEEDTHEKIDS Beer Mile

Shepherd's House Run For Recovery

Lexington, KY

Saturday, July 25th, 2026

View details for race Shepherd's House Run For Recovery

Nothing Bundt Fun 3K Run/Walk

Lexington, KY

Friday, July 31st, 2026

View details for race Nothing Bundt Fun 3K Run/Walk

Grant County Fair Mile

Williamstown, KY

Saturday, August 1st, 2026

1 Mile

View details for race Grant County Fair Mile

Back to School 5K

Danville, KY

Saturday, August 1st, 2026

1 Mile

View details for race Back to School 5K

Ninja 5K, 10K & 13.1M at Richmond, KY (32)

Richmond, KY

Saturday, August 8th, 2026

10K

Half

View details for race Ninja 5K, 10K & 13.1M at Richmond, KY (32)

A Midsummer Night's Run 5K

Lexington, KY

Saturday, August 8th, 2026

View details for race A Midsummer Night's Run 5K

Small Town America 5K Run/Walk

Mount Sterling, KY

Saturday, August 8th, 2026

View details for race Small Town America 5K Run/Walk

The Cupcake Classic 3K

Lexington, KY

Friday, August 14th, 2026

View details for race The Cupcake Classic 3K

Back The Track 5K & Woodford Track Challenge

Versailles, KY

Friday, August 14th, 2026

1 Mile

View details for race Back The Track 5K & Woodford Track Challenge

Radler Rush Cross Country 5k/10k

Frankfort, KY

Friday, August 14th, 2026

10K

View details for race Radler Rush Cross Country 5k/10k

Lions Club - Pioneer Days 5K

Harrodsburg, KY

Saturday, August 15th, 2026

View details for race Lions Club - Pioneer Days 5K

MCXC 5K

Richmond, KY

Saturday, August 15th, 2026

Trail

View details for race MCXC 5K

DV8K Life Changing Run (8K & 4K)

Lexington, KY

Saturday, August 15th, 2026

View details for race DV8K Life Changing Run (8K & 4K)

Chrysalis House 5K Run/Walk

Nicholasville, KY

Saturday, August 15th, 2026

View details for race Chrysalis House 5K Run/Walk

Triple Crown Trot 5K

Versailles, KY

Saturday, August 22nd, 2026

View details for race Triple Crown Trot 5K

A Running Start for Hope 5K

Lexington, KY

Saturday, August 22nd, 2026

View details for race A Running Start for Hope 5K

DMTL Presents: A Healthy KSU 3K & Health Fair

Frankfort, KY

Saturday, August 22nd, 2026

View details for race DMTL Presents: A Healthy KSU 3K & Health Fair

Wag Woof Walk 5K

Morehead, KY

Saturday, August 22nd, 2026

View details for race Wag Woof Walk 5K

CASA Superhero Run

Versailles, KY

Saturday, August 22nd, 2026

View details for race CASA Superhero Run

Cabernet Canter Cross Country 5K/10K

Lexington, KY

Friday, August 28th, 2026

10K

View details for race Cabernet Canter Cross Country 5K/10K

Fostering Hope 5K

Richmond, KY

Saturday, August 29th, 2026

Trail

View details for race Fostering Hope 5K

Bluegrass Reaper Challenge

Berea, KY

Saturday, August 29th, 2026

Ultra

Marathon

Half

View details for race Bluegrass Reaper Challenge

Medal Madness 5K, 10K, & 13.1M at Danville, KY ...

Danville, KY

Saturday, August 29th, 2026

10K

Half

View details for race Medal Madness 5K, 10K, & 13.1M at Danville, KY (35)

GRC Cross Country Daniel Boone 5K Honoring Davi...

Winchester, KY

Saturday, September 5th, 2026

View details for race GRC Cross Country Daniel Boone 5K Honoring David Borden

Lexington Equine Medical Hunter Pace & 5K At Th...

Lexington, KY

Saturday, September 5th, 2026

View details for race Lexington Equine Medical Hunter Pace & 5K At The Park

Chasing Hope 5K Run & 1 Mile Hope Stride

Richmond, KY

Friday, September 11th, 2026

1 Mile

View details for race Chasing Hope 5K Run & 1 Mile Hope Stride

Brothers' Run 8th Annual 3k Run/Walk Event

Versailles, KY

Saturday, September 12th, 2026

View details for race Brothers' Run 8th Annual 3k Run/Walk Event

Medal Madness 5K, 10K & 13.1M at Richmond, KY (37)

Richmond, KY

Saturday, September 12th, 2026

10K

Half

View details for race Medal Madness 5K, 10K & 13.1M at Richmond, KY (37)

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