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45 races within 25 mi of Winchester, KY

Tap a distance to add it to your season

Fri · Oct30
Graveyard Gallop 5K
Lexington, KY21 mi away
Ideal weather · 93/100 Typical: 62° / 41°F · 31% rain
Sat · Oct31
Madison Central DanceBlue For The Kids 5K
Richmond, KY17 mi away
Ideal weather · 93/100 Typical: 62° / 41°F · 31% rain
30% slower times (5K)past finishers

Sat · Nov

7

Officer Daniel Ellis Memorial 5K

Richmond, KY17 mi away

Ideal weather · 91/100 Typical: 59° / 37°F · 25% rain

4% faster times (5K)past finishers

Sat · Nov7

The Eagle Chase 5K

Lexington, KY19 mi away

Ideal weather · 91/100 Typical: 59° / 37°F · 25% rain

Sat · Nov14

Dirty Dog Trail 4 Miler

Lexington, KY15 mi away

Ideal weather · 86/100 Typical: 55° / 35°F · 26% rain

Sat · Nov14

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

Richmond, KY17 mi away

Ideal weather · 94/100 Typical: 55° / 35°F · 26% rain

Sun · Nov15

Dixie Dash 5K & Kid's Sprint

Lexington, KY21 mi away

Ideal weather · 86/100 Typical: 54° / 34°F · 26% rain

Sat · Nov21

Run for a Reason 5K

Mount Sterling, KY13 mi away

Good weather · 82/100 Typical: 52° / 33°F · 28% rain

Sat · Nov21

Southern Lights Stroll 5K

Lexington, KY21 mi away

Good weather · 82/100 Typical: 52° / 32°F · 27% rain

Sat · Nov21to Nov 22

Tough Turkey 1-day & 2-day Challenge

Nicholasville, KY24 mi away

Good weather · 82/100 Typical: 52° / 32°F · 27% rain

Sat · Nov21

Turkey Strut 5K

Nicholasville, KY24 mi away

Good weather · 82/100 Typical: 52° / 32°F · 27% rain

9% faster times (5K)past finishers

Sun · Nov22

The Gobbler Half Marathon, 10K & 5K

Lexington, KY21 mi away

Ideal weather · 89/100 Typical: 51° / 32°F · 28% rain

6% faster times (half)past finishers

Thu · Nov26

Thoroughbred Classic 5K

Lexington, KY25 mi away

Good weather · 79/100 Typical: 50° / 31°F · 30% rain

Sat · Dec12

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

Richmond, KY17 mi away

Good weather · 79/100 Typical: 44° / 28°F · 34% rain

Sat · Dec12

St. Nicholasville Ugly Sweater 3K

Nicholasville, KY24 mi away

Good weather · 72/100 Typical: 44° / 28°F · 34% rain

Sat · Dec12

YMCA REINDEER RAMBLE 5K Presented by Publix®

Lexington, KY25 mi away

Good weather · 72/100 Typical: 44° / 28°F · 34% rain

Sun · Dec20

Reindeer Runway 2 & 1/2 Mile Run/Walk

Nicholasville, KY24 mi away

Good weather · 72/100 Typical: 45° / 29°F · 36% rain

Sat · Jan9

New Year 5K, 10K, & 13.1M at Richmond, KY (02)

Richmond, KY17 mi away

Good weather · 73/100 Typical: 40° / 25°F · 33% rain

Sat · Jan30

Medal Madness 5K, 10K, & 13.1M at Richmond, KY (05)

Richmond, KY17 mi away

Good weather · 72/100 Typical: 41° / 24°F · 34% rain

Sat · Jan30

Y Not Tri

Paris, KY16 mi awayPostponed

Harsh weather · 19/100 Typical: 41° / 25°F · 34% rain

Sat · Feb13

Medal Madness 5K, 10K & 13.1M at Richmond, KY (07)

Richmond, KY17 mi away

Good weather · 73/100 Typical: 42° / 24°F · 33% rain

Sat · Mar13

Pirate 5K, 10K & 13.1M at Richmond, KY (11)

Richmond, KY17 mi away

Ideal weather · 88/100 Typical: 55° / 34°F · 35% rain

Sat · Apr3

Lions Run for Sight 5K

Lexington, KY21 mi awayRegistration opens Oct 31, 2026

Ideal weather · 86/100 Typical: 61° / 40°F · 41% rain

7% slower times (5K)past finishers

Sat · Apr10

Bunny 5K, 10K & 13.1M at Richmond, KY (15)

Richmond, KY17 mi away

Ideal weather · 88/100 Typical: 64° / 42°F · 39% rain

Sat · Apr10

Horse Capital Marathon & Half Marathon

Lexington, KY21 mi away

Ideal weather · 88/100 Typical: 64° / 42°F · 39% rain

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