Upcoming Races Near Winchester, KY

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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)

Constitution 5K Run for the Arts 2025

Danville, KY

Sunday, September 13th, 2026

View details for race Constitution 5K Run for the Arts 2025

Patriot Chase 5K Run/Walk

Richmond, KY

Sunday, September 13th, 2026

View details for race Patriot Chase 5K Run/Walk

Aphasia in Motion 5K & Fun Run

Lexington, KY

Friday, September 18th, 2026

1 Mile

View details for race Aphasia in Motion 5K & Fun Run

Run To Remember 5K

Frankfort, KY

Friday, September 18th, 2026

View details for race Run To Remember 5K

Tracks for Packs 5K Run/Walk

Richmond, KY

Saturday, September 19th, 2026

View details for race Tracks for Packs 5K Run/Walk

Harrodsburg Animal Hospital Harrodsburg Oktober...

Harrodsburg, KY

Saturday, September 19th, 2026

View details for race Harrodsburg Animal Hospital Harrodsburg Oktoberfest 5K Walk/Run

J.J. the Jet Plane Foundation 5K Color Run/Walk...

Frenchburg, KY

Saturday, September 19th, 2026

View details for race J.J. the Jet Plane Foundation 5K Color Run/Walk for Pediatric Cancer

Run4DC

Versailles, KY

Saturday, September 19th, 2026

View details for race Run4DC

Spoonbread Festival 5K

Berea, KY

Sunday, September 20th, 2026

1 Mile

Trail

View details for race Spoonbread Festival 5K

Second Stride 5K and 2.5K Run/Walk at Claiborne...

Paris, KY

Friday, September 25th, 2026

View details for race Second Stride 5K and 2.5K Run/Walk at Claiborne Farm

Montgomery County All Paws 3K

Mount Sterling, KY

Friday, September 25th, 2026

1 Mile

View details for race Montgomery County All Paws 3K

10,000 Meter on Van Meter

Winchester, KY

Saturday, September 26th, 2026

10K

View details for race 10,000 Meter on Van Meter

Scarecrow Shuffle 5k

Carlisle, KY

Saturday, September 26th, 2026

View details for race Scarecrow Shuffle 5k

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

The Raven 10K

Lexington, KY

Sunday, September 27th, 2026

10K

Trail

View details for race The Raven 10K

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

The Rugged Red Trail Half Marathon

Slade, KY

Saturday, October 3rd, 2026

Half

Trail

View details for race The Rugged Red Trail Half Marathon

Foundations 4 Hope 5K - Kentucky

Lexington, KY

Saturday, October 3rd, 2026

Trail

View details for race Foundations 4 Hope 5K - Kentucky

6th Annual Queenslake Mogadishu Mile Kentucky

Georgetown, KY

Saturday, October 3rd, 2026

1 Mile

View details for race 6th Annual Queenslake Mogadishu Mile Kentucky

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)

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

Redeeming Hope’s Rise Up & Run 5K

Richmond, KY

Saturday, October 10th, 2026

1 Mile

View details for race Redeeming Hope’s Rise Up & Run 5K

KTFMC 5K At Gainsborough Farm

Versailles, KY

Saturday, October 10th, 2026

Trail

View details for race KTFMC 5K At Gainsborough Farm

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)

The Eagle Chase 5K

Lexington, KY

Saturday, November 7th, 2026

View details for race The Eagle Chase 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

Better Together 5K

Berea, KY

Saturday, November 7th, 2026

Trail

Fast

View details for race Better Together 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)

The Red Monster

Slade, KY

Saturday, November 14th, 2026

Ultra

Trail

View details for race The Red Monster

Dirty Dog Trail 4 Miler

Lexington, KY

Saturday, November 14th, 2026

Trail

View details for race Dirty Dog Trail 4 Miler

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

St. Nicholasville Ugly Sweater 3K

Nicholasville, KY

Saturday, December 12th, 2026

View details for race St. Nicholasville Ugly Sweater 3K

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)

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

Howlin' Wolfe 25k/50k

Slade, KY

Saturday, March 27th, 2027

Ultra

Trail

View details for race Howlin' Wolfe 25k/50k

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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