Upcoming 5K Races Near Winchester, KY

Name: Freebird 5K
Start: 2026-09-12
End: 2026-09-12
Location: Lexington

K-9 YOUBE 5k Run/Walk

Ludlow, KY

Saturday, May 16th, 2026

Featured

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Fairview Baptist 5K Run For Missions

Mount Vernon, KY

Saturday, May 2nd, 2026

View details for race Fairview Baptist 5K Run For Missions

Derby Dash 5k

Williamstown, KY

Saturday, May 2nd, 2026

View details for race Derby Dash 5k

Chasing Hope 5K Run & 1 Mile Hope Stride

Berea, KY

Sunday, May 3rd, 2026

1 Mile

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

Westside 5K Derby Dash

Junction City, KY

Sunday, May 3rd, 2026

View details for race Westside 5K Derby Dash

Share Your Strength 5K Run/Walk

Danville, KY

Saturday, May 9th, 2026

View details for race Share Your Strength 5K Run/Walk

Luau 5K, 10K & 13.1M at Richmond, KY (19)

Richmond, KY

Saturday, May 9th, 2026

10K

Half

View details for race Luau 5K, 10K & 13.1M at Richmond, KY (19)

Lunch Lady Hustle 5K Run/Walk

Lexington, KY

Saturday, May 9th, 2026

Trail

Fast

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Wanda Casey Mother's Day 3K

Frankfort, KY

Sunday, May 10th, 2026

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Run The Bluegrass

Lexington, KY

Saturday, May 16th, 2026

Half

10K

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Kentucky Hands & Voices SuperHEARo 5K

Richmond, KY

Saturday, May 16th, 2026

1 Mile

View details for race Kentucky Hands & Voices SuperHEARo 5K

Milford's Merry Miles of May

Brooksville, KY

Saturday, May 16th, 2026

Fast

View details for race Milford's Merry Miles of May

2026 Run for the Paws 5k Run/Walk

Winchester, KY

Saturday, May 16th, 2026

View details for race 2026 Run for the Paws 5k Run/Walk

Run For Hope 5K

Lexington, KY

Sunday, May 17th, 2026

Trail

Fast

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

Danville, KY

Saturday, May 30th, 2026

10K

Half

View details for race Medal Madness 5K, 10K, & 13.1M at Danville, KY (22)

Pisgah Farms & Furlongs Half Mare-athon, 10K an...

Versailles, KY

Saturday, May 30th, 2026

Half

10K

View details for race Pisgah Farms & Furlongs Half Mare-athon, 10K and 5K

Alexis Thompson Memorial 5k/10K

Winchester, KY

Saturday, June 6th, 2026

10K

View details for race Alexis Thompson Memorial 5k/10K

Mountain Memories 5K

Frenchburg, KY

Saturday, June 6th, 2026

View details for race Mountain Memories 5K

MCXC 5K

Richmond, KY

Saturday, June 6th, 2026

Trail

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No Greater Honor 5K

Lexington, KY

Saturday, June 6th, 2026

1 Mile

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Medal Madness 5K, 10K & 13.1M at Richmond, KY (24)

Richmond, KY

Saturday, June 13th, 2026

10K

Half

View details for race Medal Madness 5K, 10K & 13.1M at Richmond, KY (24)

Beer Cheese 5K

Winchester, KY

Saturday, June 13th, 2026

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Wild Hearts Superhero 5K, 10K & Kids Super Sprint

Lexington, KY

Saturday, June 13th, 2026

10K

View details for race Wild Hearts Superhero 5K, 10K & Kids Super Sprint

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

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

Slade, KY

Saturday, June 27th, 2026

Trail

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Stars, Stripes & Strides 5K

Versailles, KY

Saturday, June 27th, 2026

View details for race Stars, Stripes & Strides 5K

Run Morehead 5K

Morehead, KY

Friday, July 3rd, 2026

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Blackberry Festival 5K

Carlisle, KY

Saturday, July 4th, 2026

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Bluegrass 10,000

Lexington, KY

Saturday, July 4th, 2026

10K

1 Mile

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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

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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 2.5k/5k/10k

Lexington, KY

Friday, July 24th, 2026

10K

View details for race Distillery Dash Cross Country 2.5k/5k/10k

Shepherd's House Run For Recovery

Lexington, KY

Saturday, July 25th, 2026

View details for race Shepherd's House Run For Recovery

Run White & Blue 5K & 10K

Lexington, KY

Saturday, July 25th, 2026

10K

1 Mile

Fast

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A Midsummer Night's Run 5K

Lexington, KY

Saturday, August 8th, 2026

View details for race A Midsummer Night's Run 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)

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

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

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CASA Superhero Run

Versailles, KY

Saturday, August 22nd, 2026

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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

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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

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

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

Richmond, KY

Saturday, September 12th, 2026

10K

Half

View details for race Medal Madness 5K, 10K & 13.1M at Richmond, KY (37) 30

Freebird 5K

Lexington, KY

Saturday, September 12th, 2026

1 Mile

Trail

Fast

View details for race Freebird 5K

Explore more in Winchester, KY

Distances:

5K 10K Half Marathon Marathon

Months:

May June July

Tags:

Trail Boston Qualifiers Fast Courses

State:

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