Running races in Kentucky in Oct 2027

14 races in date order

Ragnar Road Bourbon Chase
October 2027 · Clermont, KY · 206 Mile Relay
A relay across Kentucky's bourbon country

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The Bourbon Chase
October 2027 · Clermont, KY · Marathon · Half Marathon · 10K · 5K
A 200 mile relay through Kentucky bourbon country

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The Rugged Red Trail Half Marathon
October 2027 · Slade, KY · Half Marathon
Trail half through the Red River Gorge, Slade

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Tails & Tatas Breast Cancer Awareness 5k Run/Walk
October 2027 · Elizabethtown, KY · 5K · 1 Mile
Dog-friendly 5K starting at a car dealership

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Haunted 5K, 10K & 13.1M at Richmond, KY (41)
October 2027 · Richmond, KY · Half Marathon · 10K · 5K

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Monster Mash & Dash 5K Glow Run
October 2027 · Lexington, KY · 5K Run/Walk · 1 Mile Fun Walk · 0.4 km

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Paint Pikeville Pink 5K Run/Walk
October 2027 · Pikeville, KY · 5K · 1 Mile Walk

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Iron Horse Half Marathon
October 2027 · Midway, KY · Half Marathon · 12k · 5k
Rolling half marathon through Kentucky Bluegrass horse country

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LBL BRIDGE TO BRIDGE TRAIL RUN
October 2027 · Hardin, KY · Single Runner · Two Person Relay · Three Person Relay
Crossing two bridges over Kentucky's twin lakes

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The Running Pumpkin
October 2027 · Lexington, KY · 5K

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Hoptown Half Marathon and 5K
October 2027 · Hopkinsville, KY · Half Marathon · 5K

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The American Bluegrass Classic
October 2027 · Paducah, KY · Marathon · Half Marathon
Inaugural marathon debuting in Paducah, Kentucky

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Urban Bourbon Half Marathon
October 2027 · Louisville, KY · Half Marathon · 5K
Passes Louisville's bourbon distilleries downtown

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Dash For A Cure 5K
October 2027 · London, KY · 5K Run/Walk · 1 Mile Fun Walk · Kid's Dash

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← Kentucky Oct Nov Dec Jan 2027 Feb 2027 Mar 2027 Apr 2027 May 2027 Jun 2027 Jul 2027 Aug 2027 Sep 2027

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Every race here is published by its organiser; RunCalendar checks the date and the entry window against the organiser's own page and rebuilds this calendar every night. A confirmed date shows its day; a provisional one shows only its month. Last updated 22 October 2026.