Upcoming 5K Races Near Winchester, KY

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Run Baby Run 5K Benefiting NICU Babies

Lexington, KY

Saturday, September 26th, 2026

Trail

Fast

View details for race Run Baby Run 5K Benefiting NICU Babies

Fly Sam Fly 5K run/walk

Stanford, KY

Sunday, September 27th, 2026

View details for race Fly Sam Fly 5K run/walk

UK DPT 5K

Lexington, KY

Saturday, October 3rd, 2026

View details for race UK DPT 5K

Foundations 4 Hope 5K - Kentucky

Lexington, KY

Saturday, October 3rd, 2026

Trail

View details for race Foundations 4 Hope 5K - Kentucky

Redeeming Hope’s Blueheart Twilight Run 5K

Richmond, KY

Saturday, October 10th, 2026

1 Mile

View details for race Redeeming Hope’s Blueheart Twilight Run 5K

KTFMC 5K At Gainsborough Farm

Versailles, KY

Saturday, October 10th, 2026

Trail

View details for race KTFMC 5K At Gainsborough Farm

Monster Mash & Dash 5K Glow Run

Lexington, KY

Saturday, October 10th, 2026

1 Mile

Fast

View details for race Monster Mash & Dash 5K Glow Run

Haunted 5K, 10K & 13.1M at Richmond, KY (41)

Richmond, KY

Saturday, October 10th, 2026

10K

Half

View details for race Haunted 5K, 10K & 13.1M at Richmond, KY (41)

The Iron Horse Half Marathon, 12k & 5k

Midway, KY

Sunday, October 11th, 2026

Half

12K

View details for race The Iron Horse Half Marathon, 12k & 5k

The Running Pumpkin

Lexington, KY

Saturday, October 17th, 2026

View details for race The Running Pumpkin

Renfro Rock 'N Run Half Marathon / 5K

Mount Vernon, KY

Saturday, October 24th, 2026

Half

View details for race Renfro Rock 'N Run Half Marathon / 5K

Miles For Medicine 5K Run/Walk

Lexington, KY

Saturday, October 24th, 2026

1 Mile

Trail

Fast

View details for race Miles For Medicine 5K Run/Walk

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

Danville, KY

Saturday, October 31st, 2026

10K

Half

View details for race Medal Madness 5K, 10K, & 13.1M at Danville, KY (44)

Better Together 5K

Berea, KY

Saturday, November 7th, 2026

Trail

Fast

View details for race Better Together 5K

Turkey Trot for a Cure 5K Walk/Run for Alzheimer's

Morehead, KY

Saturday, November 7th, 2026

View details for race Turkey Trot for a Cure 5K Walk/Run for Alzheimer's

Officer Daniel Ellis Memorial 5K

Richmond, KY

Saturday, November 7th, 2026

View details for race Officer Daniel Ellis Memorial 5K

The Eagle Chase 5K

Lexington, KY

Saturday, November 7th, 2026

View details for race The Eagle Chase 5K

Gobbler 5K, 10K & 13.1M at Richmond, KY (46)

Richmond, KY

Saturday, November 14th, 2026

10K

Half

View details for race Gobbler 5K, 10K & 13.1M at Richmond, KY (46)

Turkey Strut 5K

Nicholasville, KY

Saturday, November 21st, 2026

View details for race Turkey Strut 5K

The Gobbler Half Marathon, 10K & 5K

Lexington, KY

Sunday, November 22nd, 2026

Half

10K

View details for race The Gobbler Half Marathon, 10K & 5K

Thoroughbred Classic 5K

Lexington, KY

Thursday, November 26th, 2026

View details for race Thoroughbred Classic 5K

Titletown Turkey Trot, Presented by DOE

Danville, KY

Thursday, November 26th, 2026

1 Mile

View details for race Titletown Turkey Trot, Presented by DOE

Woodford County Santa Shuffle 5K & Kids Elf Dash

Versailles, KY

Saturday, December 5th, 2026

View details for race Woodford County Santa Shuffle 5K & Kids Elf Dash

Frankfort Frosty 5K

Frankfort, KY

Sunday, December 6th, 2026

Trail

View details for race Frankfort Frosty 5K

Holiday 5K, 10K & 13.1M at Richmond, KY (50)

Richmond, KY

Saturday, December 12th, 2026

10K

Half

View details for race Holiday 5K, 10K & 13.1M at Richmond, KY (50)

St. Nicholasville Ugly Sweater 3K

Nicholasville, KY

Saturday, December 12th, 2026

View details for race St. Nicholasville Ugly Sweater 3K

Frosty Feet 5K

Richmond, KY

Saturday, January 30th, 2027

10K

View details for race Frosty Feet 5K

Hillbilly Hustle 5K & 10K

Georgetown, KY

Saturday, March 27th, 2027

10K

View details for race Hillbilly Hustle 5K & 10K

Brandon True Memorial Heroes For The Homeless 5...

Lexington, KY

Saturday, April 17th, 2027

1 Mile

Trail

Fast

View details for race Brandon True Memorial Heroes For The Homeless 5K Presented by Anderson Communities

Westside 5K Derby Dash

Junction City, KY

Sunday, May 2nd, 2027

View details for race Westside 5K Derby Dash

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