Upcoming Races Near Winchester, KY

Organize a race? Get it in front of thousands of runners.

Add it free Feature it

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

KTFMC 5K At Gainsborough Farm

Versailles, KY

Saturday, October 10th, 2026

Trail

View details for race KTFMC 5K At Gainsborough Farm

Forkland Festival Fox and Hound 4K

Gravel Switch, KY

Saturday, October 10th, 2026

Trail

View details for race Forkland Festival Fox and Hound 4K

The Tri-County Kentucky United Way Spirit 5K

Bardstown, KY

Saturday, October 10th, 2026

View details for race The Tri-County Kentucky United Way Spirit 5K

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

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

Little Rooster Run

Glencoe, KY

Friday, October 16th, 2026

Ultra

View details for race Little Rooster Run

Knox/Whitley Humane Association 5K Mutt Strut a...

CORBIN, KY

Saturday, October 17th, 2026

1 Mile

Fast

View details for race Knox/Whitley Humane Association 5K Mutt Strut and Dogwalk

The Running Pumpkin

Lexington, KY

Saturday, October 17th, 2026

View details for race The Running Pumpkin

LCRH Run and Walk To Remember 5K

Somerset, KY

Saturday, October 17th, 2026

View details for race LCRH Run and Walk To Remember 5K

Dash For A Cure 5K

London, KY

Sunday, October 18th, 2026

1 Mile

Fast

View details for race Dash For A Cure 5K

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

Red Wolf Rampage

Rising Sun, IN

Saturday, October 24th, 2026

10K

Trail

View details for race Red Wolf Rampage

Little Batty Trail Runs

Nancy, KY

Sunday, October 25th, 2026

Half

10K

Trail

View details for race Little Batty Trail Runs

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)

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

The Wildcat @ General Butler

Carrollton, KY

Saturday, November 7th, 2026

10K

Half

Trail

View details for race The Wildcat @ General Butler

Better Together 5K

Berea, KY

Saturday, November 7th, 2026

Trail

Fast

View details for race Better Together 5K

The Eagle Chase 5K

Lexington, KY

Saturday, November 7th, 2026

View details for race The Eagle Chase 5K

Officer Daniel Ellis Memorial 5K

Richmond, KY

Saturday, November 7th, 2026

View details for race Officer Daniel Ellis Memorial 5K

Dirty Dog Trail 4 Miler

Lexington, KY

Saturday, November 14th, 2026

Trail

View details for race Dirty Dog Trail 4 Miler

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

Bleeding Disorders of Kentucky Hemo Hustle

Shelbyville, KY

Saturday, November 14th, 2026

View details for race Bleeding Disorders of Kentucky Hemo Hustle

Honor Run Half Marathon

Florence, KY

Sunday, November 15th, 2026

Half

10K

View details for race Honor Run Half Marathon

St. Vincent De Paul Turkeyfoot Trot

Crestview Hills, KY

Saturday, November 21st, 2026

View details for race St. Vincent De Paul Turkeyfoot Trot

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

Titletown Turkey Trot, Presented by DOE

Danville, KY

Thursday, November 26th, 2026

1 Mile

View details for race Titletown Turkey Trot, Presented by DOE

Thoroughbred Classic 5K

Lexington, KY

Thursday, November 26th, 2026

View details for race Thoroughbred Classic 5K

Turkey Fun Run & Family Stroll 5K

Bardstown, KY

Thursday, November 26th, 2026

View details for race Turkey Fun Run & Family Stroll 5K

Pilgrimage in the Park 5K Run/Walk

Nancy, KY

Thursday, November 26th, 2026

1 Mile

Trail

View details for race Pilgrimage in the Park 5K Run/Walk

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

Topo Trail Marathon Races

Bethel, OH

Sunday, December 6th, 2026

10K

Half

Marathon

Trail

View details for race Topo Trail Marathon Races

Frankfort Frosty 5K

Frankfort, KY

Sunday, December 6th, 2026

Trail

View details for race Frankfort Frosty 5K

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

Richmond, KY

Saturday, December 12th, 2026

10K

Half

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

Christmas Island Jingle Bell Run

Burnside, KY

Saturday, December 12th, 2026

View details for race Christmas Island Jingle Bell Run

St. Nicholasville Ugly Sweater 3K

Nicholasville, KY

Saturday, December 12th, 2026

View details for race St. Nicholasville Ugly Sweater 3K

Frozen Nuts Trail Run

Nancy, KY

Saturday, January 9th, 2027

Half

10K

Trail

View details for race Frozen Nuts Trail Run

Frosty Feet 5K

Richmond, KY

Saturday, January 30th, 2027

10K

View details for race Frosty Feet 5K

Shamrock Shuffle 5K

Somerset, KY

Saturday, March 13th, 2027

View details for race Shamrock Shuffle 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

Beechwood PTSA Tiger Trail 5K

Ft Mitchell, KY

Saturday, April 24th, 2027

Trail

View details for race Beechwood PTSA Tiger Trail 5K

Westside 5K Derby Dash

Junction City, KY

Sunday, May 2nd, 2027

View details for race Westside 5K Derby Dash

Mount Washington Spring Festival 5K (May 8. 2027)

Mt Washington, KY

Saturday, May 8th, 2027

View details for race Mount Washington Spring Festival 5K (May 8. 2027)

Buffalo Trace Stampede

Maysville, KY

Saturday, June 12th, 2027

1 Mile

Fast

View details for race Buffalo Trace Stampede

Prev 1 2

Explore more in Winchester, KY

Jump straight to races by distance, month, or type.

Distance

5K 10K Half Marathon Marathon

Month

June July August

Race type

Trail Boston Qualifiers Fast Courses

Run clubs

Run clubs in Winchester

Nearby

Lexington Richmond Nicholasville Georgetown Berea Versailles All Kentucky races