44 running, walking, cycling, and other events in Lexington, Kentucky

From big races to Saturday morning group runs—find running, walking, cycling, and fun run events and connect with the local endurance sports community.

• Seton Catholic School Run for the Nun 5K [runsignup.com]
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  Sat, May 30, 2026 at 7:45 AM

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  A running tradition in Lexington since 1990!

  Join us for the 36th Anniversary of Seton Catholic's Run For The Nun 5K & Kids 1/3 Mile Fun Run/Walk to be held on Saturday, May 30, 2026 at 8:00am.

  RACE...

  A running tradition in Lexington since 1990!

  Join us for the 36th Anniversary of Seton Catholic's Run For The Nun 5K & Kids 1/3 Mile Fun Run/Walk to be held on Saturday, May 30, 2026 at 8:00am.

  RACE FEATURES

  • Scenic 5K Course

  • Commemorative race T-shirts

  • Overall, Age Group and Team Awards

  • Kids 1/3 Mile Dash (7:45am)

  Overall awards (top 3 M/F) will be based on gun time (head to head competition) and age group awards (top 3 M/F) will be based on chip time. Age groups are 14 & under, 15-19, 20-24, 25-29, 30-34, 35-39, ..., 70-74, 75-79, 80 & over.

  3.1 Miles 5k Fun Run Run Walk

  1730 Summerhill Drive, Lexington, Kentucky, 40515, United States
  OpenStreetMap Google Maps
• No Greater Honor 5K [nogreaterhonorrun.org] [Register at runsignup.com]
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  Sat, Jun 06, 2026 at 12:00 AM

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  Join us for the 6th Annual No Greater Honor 5K Run presented by Honor Flight Kentucky. Run or walk 3.1 miles and receive a commemorative race shirt.

  SATURDAY, JUNE 6, 2026, AT 8:00AM AT KEENELAND...

  Join us for the 6th Annual No Greater Honor 5K Run presented by Honor Flight Kentucky. Run or walk 3.1 miles and receive a commemorative race shirt.

  SATURDAY, JUNE 6, 2026, AT 8:00AM AT KEENELAND RACECOURSE

  This race is about honoring our veterans and supporting a great local cause, Honor Flight Kentucky. (Read more about their mission below.) Our race will feature a scenic 5K route on the historic Keeneland Racecourse grounds, commemorative men's/women's/youth sized race T-shirts, free race photos, overall & age group awards and more.

  RACE FEATURES:

  • Scenic course at Keeneland Racecourse

  • Free Race Photos

  • Commemorative Performance/Tech Race Shirts

  • Overall and Age Group Awards

  • 5K, 1 Miler and Kids Dash plus a Virtual Option for those who can't join us in person

  • Walkers welcomed!

  We've enabled SOCIAL TEAMS for this race. Expand your race day fun by starting or joining a social team. Invite your friends, family, & co-workers to join your team. We'll have a prize for the largest team, and teams of 5 or more SAVE $3.00 per team member.

  PACKET PICKUP Our packet pickup will be held on Friday, June 5th from 4-6pm at J&H Running Company (197 Moore Drive in Lexington!. There will also be race morning packet pickup offered from 7:00-8:15am. You can pickup for friends/family with no credentials, paperwork or ID necessary.

  DISCOUNT FOR VETERANS & ACTIVE DUTY MILITARY Use coupon code SERVICE at online checkout to SAVE $5 on your registration. Thank you for your service!!!

  Our online registration will remain open until race morning.

  5K ROUTE MAP

  1k 1 Miles 3.1 Miles 5k Run Virtual Walk

  Lexington, Kentucky, 40510, United States
  OpenStreetMap Google Maps
• Wild Hearts Superhero 5K, 10K & Kids Super Sprint [kerringtonsheart.org] [Register at runsignup.com]
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  Sat, Jun 13, 2026 at 12:00 AM

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  Join us for our Superhero themed races which offer something for everyone (5K Run/Walk, 10K Run & Kids Super Sprint)!

  SATURDAY, JUNE 13, 2026 *** KID"S SUPER SPRINT - 7:30AM, 5K & 10K - 8:00AM ***...

  Join us for our Superhero themed races which offer something for everyone (5K Run/Walk, 10K Run & Kids Super Sprint)!

  SATURDAY, JUNE 13, 2026 *** KID"S SUPER SPRINT - 7:30AM, 5K & 10K - 8:00AM *** KEENELAND RACECOURSE

  RACE FEATURES:

  • Scenic course at the historic Keeneland Racecourse (Lexington KY)

  • Commemorative Race Shirts & Enamel Collector Pins

  • Superhero themed race --- Prizes for: Superhero Boy & Girl, Superhero Man & Woman, Super Pet, Super Stroller & Best T-shirt

  • Chip timed (5K and 10K) --- Thanks RaceRise

  • Free Race Photos

  • DJ James Hummel (Freestyle Entertainment)

  • 10K - Finisher Medals, Overall & Age Group Pins

  • 5K - Overall & Age Group Medal Awards

  • Age Groups (5K & 10K) - 0-11, 12-15, 16-19, 20-24, 25-29 .... (5 year) ... 75-79, 80+

  • Kids Super Sprint (Ages 2-10) - receive a participant medal

  Our race supports Kerrington's Heart. We provide hope, help and healing to CHD families.

  The purpose of this event is not only to increase overall awareness concerning Congenital Heart Defects (CHD), but to raise funds in furtherance of our mission to provide education, support, and encouragement for children with heart disease, their families, and caregivers.

  CHD is the #1 birth defect in America, and we’re fighting every day to make a difference in the lives of Kentucky families affected by this condition.

  Visit our non-profit online at www.kerringtonsheart.org.

  5K ROUTE MAP

  10K ROUTE MAP

  PACKET PICKUP:

  Friday June 12th from 3:00pm-6:00pm

  Greyline Station (beside North Lime Coffee & Donuts)

  101 West Loudon Street, Lexington, KY 40508

  Picking up for family, friends and team members is highly encouraged. The more racers that can pick up on Friday the better for all! Expect long lines for those picking up day of race event.

  3.1 Miles 5k 10k Kids Run Sprint Super Sprint Walk

  Lexington, Kentucky, 40510, United States
  OpenStreetMap Google Maps
• Bluegrass 10,000 [runsignup.com]
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  Sat, Jul 04, 2026 at 12:00 AM

  Description

  Join us for the 50th Annual Bluegrass 10,000 on Saturday, July 4th, 2026.

  COURSE RECORDS

  Female: Katy Kunc 33:33.7 (2021)

  Male: Marcus Nenow 29:14 (1983)

  Push Rim Wheelchair Female: Aerelle Jones 32:09 (2018)

  Push Rim Wheelchair Male: Paul Dietrich 24:19 (1996)

  Hand-Cranked Wheelchair Male: Greg Queen 18:45 (2014)

  Hand-Cranked Wheelchair Female: Carley Pearson 25:44 (2014)

  1 Miles 3.1 Miles 6.2 Miles Run Wheelchair

  Lexington, Kentucky, 40507, United States
  OpenStreetMap Google Maps
• Distillery Dash Cross Country 5k/10k [runsignup.com]
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  Fri, Jul 24, 2026 at 7:00 PM

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  The Distillery Dash is the first in a three part XC series collaborating with local distilleries, breweries and wineries! Sign up early for the lowest prices, and Run for Bourbon!

  The Distillery Dash...

  The Distillery Dash is the first in a three part XC series collaborating with local distilleries, breweries and wineries! Sign up early for the lowest prices, and Run for Bourbon!

  The Distillery Dash will feature a 5k and 10k cross-country race options at beautiful Masterson Station Park. All participants will receive a race t-shirt, finisher's award, and a bourbon tasting drink ticket.

  Participants under 21 will receive all portions of the finisher award except for the tasting tickets.

  The afterparty will run until 10:00 p.m., so hang around for music, bourbon tastings, drink sales, food trucks, and a great time! Register for all three races in the series for a special finisher's award at the end of the series!

  The 5k will be open to walkers, but we will enforce a cutoff pace of 16 minutes/mile for the 10k due to concerns with sunset.

  Event Map

  Packet Pickup

  Packet Pickup prior to Race Day TBD

  Race day packet pickup: Friday, July 24, 6 p.m. - 6:45 p.m. at the Masterson Station Fairgrounds.

  If possible, please pick up your packet early to help ensure a smoother race day. You may also pick up for friends.

  Register for all three races in the Beer, Bourbon & Wine Series for a special finisher's award at the end of the series!

  Race 1 - Race 2 - Race 3

  The Central Kentucky Beer, Bourbon & Wine Cross Country Series is presented by John’s Bluegrass Racing Company and sponsored by Diadora.

  5k 10k Run Walk

  3051 Leestown Rd, Lexington, Kentucky, 40511, United States
  OpenStreetMap Google Maps
• Run White & Blue 5K & 10K [runsignup.com]
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  Sat, Jul 25, 2026 at 12:00 AM

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  Join us for this 3rd Annual race that celebrate the life & legacy of CPT. Alan Kurre Elliott!

  Saturday, July 25, 2026, at 8:00am at Coldstream Park in North Lexington

  We race to make a difference and...

  Join us for this 3rd Annual race that celebrate the life & legacy of CPT. Alan Kurre Elliott!

  Saturday, July 25, 2026, at 8:00am at Coldstream Park in North Lexington

  We race to make a difference and honor a life well lived. The “CPT. Alan Kurre Elliott Memorial Run” is more than just a race; it is a tribute to a remarkable person, and an opportunity to give back. All proceeds will fund the “CPT. Alan Kurre Elliott Memorial Student Award” for undergraduate students in the Kinesiology Department at the University of Kentucky who embody Alan’s outstanding character. (Read more below)

  RACE FEATURES:

  • Flat/fast 5K and 10K courses at scenic Coldstream Park in North Lexington

  • Commemorative super soft poly/cotton T-shirts

  • Patriotic themed race

  • Awards for Top 3 M/F Overall and Top 3 M/F in 10-year age groups (5K & 10K)

  • Free Race Photos (Thanks Ruby Cline-Eaton!)

  • Social teams to enhance your race experience (Prize for the largest team)

  • Convenient race morning packet pickup

  • 5K run/walk, 10K run (chip timed), 2 Mile Ruck/Walk (untimed) and virtual option

  • Food, fun, music and fellowship for a great cause

  PACKET PICKUP Our PPU plans will be announced closer to the race date. We will definitely have race morning packet pickup at Coldstream Park from 6:45-8am.

  5K ROUTE MAP

  10K ROUTE MAP

  The 10K ROUTE will just do the 5K out and back route twice. There will be a turnaround just in front of the 5K finish line with a water station at that point. 10K participants will turn at that point and run the same 5K course a 2nd time.

  NEW FOR 2026 --- We've added a 2 Mile Walk/Ruck

  CPT Elliott set off on Sunday, July 30, 2023, intending to complete a ruck march in preparation for an upcoming tryout with Special Mission Unit. Two miles into his run/ruck, he has hit and killed in a hit-and-run. This year, we will be changing Run, White, & Blue’s “1-mile fun run/walk” to 2 miles in tribute and encourage all who would like to honor Alan and other service members lost in the line of duty to complete the 2 miles carrying a rucksack.

  1 Miles 3.1 Miles 5k 6.2 Miles 10k Fun Run Run Virtual Walk

  Lexington, Kentucky, 40511, United States
  OpenStreetMap Google Maps
• Shepherd's House Run For Recovery [runsignup.com]
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  Sat, Jul 25, 2026 at 8:00 AM

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  The Shepherd’s House is hosting the 27th Annual Run for Recovery 5K and Fun Walk. We are EXCITED to be BACK AT KEENELAND again in 2026 offering a live event. Again this year a VIRTUAL Run/Walk option...

  The Shepherd’s House is hosting the 27th Annual Run for Recovery 5K and Fun Walk. We are EXCITED to be BACK AT KEENELAND again in 2026 offering a live event. Again this year a VIRTUAL Run/Walk option will be available for those who prefer to participate remotely and still support the Shepherd's House. The Shepherd’s House operates several Recovery Treatment Programs throughout Central Kentucky ranging from In-Patient, Intensive Out-Patient, Recovery Housing, Community Impact, Recovery Community Center, and Jail Substance Abuse Programs. All of our programs are highly structured programs that promote personal responsibility, accountability, and life skills to successfully live in recovery.

  This fundraising event is a celebration of recovery and attracts both serious and recreational runners, walkers, and dogs. This event has something for everyone. Family friendly, pet friendly, and supports a great mission! We can't wait to see you at Keeneland in July 2026! Join us in Celebrating Recovery in the Bluegrass!

  5k Run Virtual Walk

  AM, Lexington, Kentucky, 40510, United States
  OpenStreetMap Google Maps
• A Midsummer Night's Run 5K [runsignup.com]
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  Sat, Aug 08, 2026 at 12:00 AM

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  Let's close out the summer with Lexington's most exciting race!

  The 42nd Annual A Midsummer Night's Run!

  The 2026 A Midsummer Night's Run presented by CHI Saint Joseph Health is a live, in-person...

  Let's close out the summer with Lexington's most exciting race!

  The 42nd Annual A Midsummer Night's Run!

  The 2026 A Midsummer Night's Run presented by CHI Saint Joseph Health is a live, in-person race in downtown Lexington scheduled for Saturday, August 8, 2026 at 7:30pm. We are providing a virtual participant option for those who can't (or choose not to) join us in person. Additionally the Fastest Kid In Town Kids Races (Ages 2-12) will be held at 6pm.

  RACE DAY SCHEDULE (Saturday, August 8, 2026)

  • 4:30PM --- Packet Pickup Opens (Packet Pickup Tent on Courthouse Plaza Lawn)

  • 5:45PM --- Fastest Kid In Town Meeting with Parents/Kids (Corner of Limestone & Short Streets)

  • 6:00PM --- Fastest Kid in Town Races (Ages 2-12)

  • 7:20PM --- Brief Pre-Race Program

  • 7:30PM --- A Midsummer Night's Run 5K START

  • 8:00PM --- Awards Tent Open (For pickup of Age Group Awards (Top 3 M/F in each 5 year division)

  • 8:15PM --- Awards Presented to Top 3 Male & Female Overall winners

  RACE FEATURES

  • A unique downtown race in the heart of Lexington, Kentucky

  • Commemorative race T-shirts

  • 5K Run/Walk and Fastest Kid In Town (Ages 2-12)

  • Awards for top Overall & Age Group finishers

  • Free Race Photos

  • Team Pricing (Teams of 5 or more SAVE $5 on each team member's registration fee)

  • Virtual Option for those who can't join the race in-person

  • DJ & Food Trucks

  RACE DONATIONS All race donations made by A Midsummer Night’s Run participants will support the Saint Joseph Hospital Foundation’s Yes, Mamm! program which provides free mammography screening, diagnostics services, and program support to uninsured or underinsured women and men.

  PACKET PICKUP There will be two prerace packet pickup opportunities. We encourage all local runners to pickup in advance. You can pickup for friends, family and team members with no credentials, paperwork or ID's required.

  • Packet Pickup #1: Location TBD, Thursday, August 6th from 12pm-6pm

  • Packet Pickup #2: Location TBD, Friday, August 7th from 2pm-7pm

  5K AWARDS Awards will be presented to the Top 3 M/F Overall finishers and Top 3 M/F in the following Age Groups (0-14, 15-19, 20-24, 25-29, 30-34, 35-39, 40-44, 45-49, 50-54, 55-59, 60-64, 65-69, 70-74, 75-79, & 80+)

  5K ROUTE MAP

  3.1 Miles 5k Run Virtual Walk

  Lexington, Kentucky, 40507, United States
  OpenStreetMap Google Maps
• DV8K Life Changing Run (8K & 4K) [runsignup.com]
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  Sat, Aug 15, 2026 at 6:30 AM

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  Some run for fun. Some run for health. Now, run to change a life.

  Support the DV8 Kitchen Vocational Training Foundation's

  Employee Success Program!

  Join us for the 8th Annual DV8K Life Changing Run...

  Some run for fun. Some run for health. Now, run to change a life.

  Support the DV8 Kitchen Vocational Training Foundation's

  Employee Success Program!

  Join us for the 8th Annual DV8K Life Changing Run on Saturday, August 15, 2026, at 8:00 a.m. at Keeneland Racecourse.

  The race will feature our signature 8K (4.97 miles), a 4K (2.5 miles) run/walk, and Kids' 1/4 Mile Dash. The races will cover much of the scenic Keeneland grounds. Run or walk the 4K with strollers welcomed. The 8K is a double loop course and only for runners who can maintain a 15 minute/mile pace.

  We also have a Virtual Runner/Walker category for those who want to support the race and cause, but who cannot join us in person. Register as a virtual runner/walker, and we'll mail your race packet (bib & race shirt), and you can run/walk your own DV8K or 4K on your own timeline anywhere in the world.

  The 2026 DV8K Run will raise funds to further DV8's mission of employing and empowering people in early stages of addiction recovery.

  RACE FEATURES

  • Awesome unique course at historic Keeneland Racetrack

  • Race produced and chip timed by RaceRise

  • DJ Stitz keeping the energy upbeat

  • 8K Awards - Overall Top 3 M/F & Top 3 M/F Age Groups (5-year divisions), 4K Awards - Top 3 M/F Overall

  • Commemorative men's/unisex sized race t-shirts (while supplies last)

  • Post-race eats from DV8 Kitchen

  • All participants who pick up packet on Thursday receive a race goodie bag with coupon for a complimentary cinnamon roll or breakfast sandwich

  • Walkers & strollers welcomed for our 4K distance race

  • Kids' 1/4-mile Dash (kids receive a commemorative shirt)

  • Food, fun and fellowship for a great local cause!

  8K Age Group Awards: 0-14, 15-19, 20-24, 25-29, 30-34, 35-39, 40-44, 45-49, 50-54, 55-59, 60-64, 65-69, 70+

  PACKET PICKUP

  Thursday, August 13th from 4-7pm at DV8 Kitchen East End Location

  There will be race day packet pickup from 6:45-7:45 a.m. at Keeneland.

  FORM A LIFE-CHANGING TEAM AND SAVE!

  Form a Life-Changing Team of 5 or more runners/walkers, and you can all SAVE $3 on your individual registrations. Teams can be as large as you want.

  It's simple to CREATE A TEAM when you register. Give yourself a TEAM NAME (the more creative, the better!) and invite your friends, family, running buddies, or co-workers to join your team. When they register (after you), they will be able to select your team from a list of existing teams. For the team pricing, the first 4 members of a team will pay full price. The 5th person joining + anyone joining the team afterward will pay the current registration fee with a $3 discount. When the 5th person joins to fully consummate a 5 person team, the first 4 registrants will each be refunded $3 on their credit card. Team members can be participating in any of our four events: the 8K, 4K, 1K Kids' Dash, or Virtual Run/Walk. If you want to create a password to be shared and used when your team members join the team, that is allowed (but not required). There will be no formal competition between the teams other than our recognizing the largest team, but this gives you a way to save and get your friends

  and family involved in this fun race.

  Don't go it alone — FORM A LIFE CHANGING TEAM and save!

  8K ROUTE MAP

  4K ROUTE MAP

  1k 4k 8k Run Virtual Walk

  Lexington, Kentucky, 40510, United States
  OpenStreetMap Google Maps
• Cabernet Canter Cross Country 5K/10K [runsignup.com]
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  Fri, Aug 28, 2026 at 6:45 PM

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  Run for wine at the eighth annual Cabernet Canter Cross Country 5K/10K at Talon Winery!

  Participants will run a beautiful cross-country race at Talon Winery, and receive a finishers award and drink...

  Run for wine at the eighth annual Cabernet Canter Cross Country 5K/10K at Talon Winery!

  Participants will run a beautiful cross-country race at Talon Winery, and receive a finishers award and drink ticket redeemable for one glass of Talon wine. Participants under 21 will receive all portions of the finisher award except for the glass of wine.

  Stick around after the event to shop the great selection of wines and hang out with live music! The after-party will run until 10 p.m. in the Talon Winery tasting room and Monarch Pavilion.

  Packet Pickup

  TBD

  Race day packet pickup: Friday, August 29, 6 p.m. - 6:45 p.m. at the Talon Winery Tasting Pavilion.

  If possible, please pick up your packet early to help ensure a smoother race day. You may also pick up for friends.

  The Central Kentucky Beer, Bourbon & Wine Cross Country Series is presented by John’s Bluegrass Racing Company and sponsored by Diadora.

  5k 10k Run

  7086 Tates Creek Road, Lexington, Kentucky, 40515, United States
  OpenStreetMap Google Maps
• Freebird 5K [runsignup.com]
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  Sat, Sep 12, 2026 at 12:00 AM

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  Join us for the 2nd Annual Freebird 5K Run/Walk honoring the life & legacy of Charles "Charlie" O'Connell.

  SATURDAY, SEPTEMBER 12, 2026 AT 8:00AM AT COLDSTREAM DOG PARK/LEGACY TRAIL

  RACE FEATURES:

  *...

  Join us for the 2nd Annual Freebird 5K Run/Walk honoring the life & legacy of Charles "Charlie" O'Connell.

  SATURDAY, SEPTEMBER 12, 2026 AT 8:00AM AT COLDSTREAM DOG PARK/LEGACY TRAIL

  RACE FEATURES:

  • Flat/fast and scenic course at Coldstream Park/Legacy Trail

  • Commemorative unisex sized T-shirts (Or select the No Shirt option)

  • 5K Run/Walk, 1 Miler (untimed) Fun Walk & Virtual Option

  • Overall Top 3 M/F & Top 3 M/F Age Group Awards (0-14, 15-19, 20-24 and 5-year groups to 65-69, 70+)

  • Free Race Photos (Thanks Paul Martin Photography) & Finish Line Photo Contest

  • Social Teams to Enhance Your Race Experience (Prize for the largest team)

  • Convenient race morning Packet Pickup at Coldstream Park

  • Food, fun and fellowship as we honor a great Lexingtonian and his legacy

  Our race will benefit the Lexington Public Safety Museum which is dedicated to preserving, collecting, and exhibiting the history of all public safety agencies within Fayette County, Kentucky. It serves as an ambassador and advocate for public safety, promoting safety awareness, diversity, and collective heritage.

  Charles “Charlie” O’Connell July 5, 1954 – September 16, 2021; A larger than life spirit that is still felt within Lexington! Affectionately called Charlie ‘O by many that knew him, he was a husband, a son, a brother, an uncle and a beloved friend of so many! Charlie was as public servant to the core. He was always ready to offer a helping hand to anyone in need! Charlie devoted his life to public safety! Charlie worked for UKPD, Lexington PD, Lexington E911 as a PD Dispatcher and Fire Dispatch Supervisor. Charlie had a public safety heart, a servant leader. Charlie left everyone he came in contact better! Charlie was a music enthusiast and adventurous! Whether he was running, bicycling, riding in his convertible, motorcycling, or flying his Cessna he loved the feeling of the wind. He loved feeling free! Our 5K was founded in honor of Charlie’s legacy in public safety. Fly high Charlie O' ---- Freebird!

  1 Miles 3.1 Miles 5k Cycling Run Trail Virtual Walk

  Lexington, Kentucky, 40511, United States
  OpenStreetMap Google Maps
• Susan Bradley-Cox Tri for Sight Triathlon/Duathlon [runsignup.com]
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  Sun, Sep 13, 2026 at 7:45 AM

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  The Susan Bradley-Cox Tri for Sight will be hosted by The Club at UK’s Spindletop Hall, on Sunday, September 13, 2026. The USAT-sanctioned event features a 400-meter swim in a heated, outdoor pool...

  The Susan Bradley-Cox Tri for Sight will be hosted by The Club at UK’s Spindletop Hall, on Sunday, September 13, 2026. The USAT-sanctioned event features a 400-meter swim in a heated, outdoor pool with a time trial start on 15-second intervals. The duathletes will instead be treated to a relatively flat, fast and scenic 2-mile run behind and beside Spindletop. Both Tri and Du events will then transition to a 12.6-mile bike course on low-traffic roads in the beautiful horse country located just east of the Kentucky Horse Park. The Tri and Du events both finish with a 3 mile run.

  The aqua-bike will have the same format as the triathlon for the swim and bike stages. ATTENTION: Aqua-bike athletes timing will end upon re-entering the transition area after the bike stage.

  Aqua-run athletes will start the swim once the last triathlete/aqua-biker is out of the pool and then do the same swim course, followed by a quick transition and out onto the 3-mile run course.

  Must register by Wednesday, July 29, 2026 to ensure you receive your desired shirt size.

  Aquabike Cycling Duathlon Run Swim Triathlon

  Lexington, Kentucky, 40511, United States
  OpenStreetMap Google Maps
• Bourbon Burn [bourboncountryburn.com] [Register at runsignup.com]
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  Thu, Sep 24, 2026 at 2:00 PM

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  Event Date: September 25th - 27th, 2026

  Location: Kentucky Horse Park Campground, Lexington, KY

  The Bourbon Burn — part bike tour, part bourbon festival — is a three-day, fully-supported bicycle tour...

  Event Date: September 25th - 27th, 2026

  Location: Kentucky Horse Park Campground, Lexington, KY

  The Bourbon Burn — part bike tour, part bourbon festival — is a three-day, fully-supported bicycle tour of the bourbon distilleries and Thoroughbred horse farms of central Kentucky. Explore quiet country roads and quaint communities en route to distilleries nestled amongst the rolling bluegrass hills. Daily distance options range from 20 - 100+ miles and stop at numerous distilleries big and small throughout the event.

  Back at Bourbon Base Camp - located at the Kentucky Horse Park Campground in Lexington, KY - sip local bourbon from the same distilleries you biked to that day (plus others!) and enjoy live entertainment as you mix and mingle with friends, old and new. Registration is open to riders 21+ (by event date).

  The Burn offers loops departing from the Bourbon Base Camp each morning. Decide each day just how much Burn you want to earn, with short, medium, or long options ranging from 20 - 100+ miles. The best part of a loop ride? You won't have to pack up your tent or check out of your hotel room all weekend!

  In addition to a 3-day registration, we also offer a 2-day registration option for those who are not able to attend the full experience.

  Cycling

  Lexington, Kentucky, 40511, United States
  OpenStreetMap Google Maps
• Run Baby Run 5K Benefiting NICU Babies [runsignup.com]
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  Sat, Sep 26, 2026 at 12:00 AM

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  Join us for this fun 5th annual race at Coldstream Park to support NICU babies.

  The 5th Annual RUN BABY RUN 5K will be held on Saturday, September 26, 2026 at 9:00am at Coldstream Park/Legacy Trail...

  Join us for this fun 5th annual race at Coldstream Park to support NICU babies.

  The 5th Annual RUN BABY RUN 5K will be held on Saturday, September 26, 2026 at 9:00am at Coldstream Park/Legacy Trail in Northwest Lexington. Run/walk in-person or join us as a virtual participant and run/walk your 3.1 miles from anywhere. We also have a Kid's Dash (1/4 mile) for kiddos 10 and under!

  RACE FEATURES:

  • Flat/fast course on the Legacy Trail through scenic Coldstream Park

  • Commemorative race T-shirts

  • Free race photos (Thanks Ruby Cline-Eaton)

  • Chip timing (Thanks RaceRise)

  • Awards for Top 3 M/F Overall and Age Groups (5-year divisions)

  • Social teams to expand your race fun/experience (We'll have a prize for the largest team)

  • 5K run/walk, Kid's 1/4 Mile Dash and Virtual option

  • Food, fun and fellowship

  5K ROUTE MAP

  PACKET PICKUP We will be holding our packet pickup on race morning (Saturday, 9/26/26) from 7:30-8:45am at Coldstream Park. If the size of the race grows to the point of needing an advanced day PPU then we'll announce those details.

  3.1 Miles 5k Run Trail Virtual Walk

  Coldstream Park/Legacy Trail, Lexington, Kentucky, 40511, United States
  OpenStreetMap Google Maps
• The Raven 10K [runsignup.com]
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  Sun, Sep 27, 2026 at 12:00 AM

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  Join us for the 12th annual Raven 10K Trail Run on the grounds of Raven Run Nature Sanctuary.

  Our 2026 in-person race will be held on Sunday, September 27th at 9:00am. There will also be a Raven 10K...

  Join us for the 12th annual Raven 10K Trail Run on the grounds of Raven Run Nature Sanctuary.

  Our 2026 in-person race will be held on Sunday, September 27th at 9:00am. There will also be a Raven 10K Virtual option for those who want to participate on their own schedule.

  The race is presented by Lexington Parks & Recreation!

  REGISTRATION FEE: $42 Raven 10K (In-person) until September 13th at 11:59pm, $50 after. - $30 Raven 10K (virtual)

  Race Capacity: 170 Runners (Limit in place due to parking capacity at the park)

  PACKET PICKUP: TBD

  LAST CHANCE PACKET PICKUP: Sunday, September 27th 7:30 - 8:30am at Raven Run Nature Sanctuary. - 3885 Raven Run Way, Lexington, KY 40515

  RACE DAY --- ARRIVE BY 8:30AM We ask all participants to arrive and be checked in by 8:30am. We'll have a mandatory runner meeting at 8:55am. We'll start the race promptly at 9:00am.

  VIRTUAL RUN/WALK/HIKE OPTION: For those who would like to participate but can't or don't want to join us for the in-person event, we have a virtual option for $30, $25 without a shirt. You run/walk/hike your 10K prior to September 28th, and you'll earn a commemorative race shirt. There are no awards or results submission for the virtual, all on the honor system. You can run/walk/hike your 10K (6.2 miles) from Raven Run Nature Sanctuary or the local/route of your choice. Race shirts will be mailed to virtual participants.

  TIME/PACE LIMIT: We have use of the park until 11:30am, so our race has a 2.5-hour (24 minute/mile) pace limit.

  AWARDS: We will present awards following the race to the Top 3 M/F Overall finishers as well as the Top 3 M/F in the following age groups (0-9, 10-19, 20-24, 25-29, 30-34, 35-39, 40-44, 45-49, 50-54, 55-59, 60-64, 65-69, 70+

  6.2 Miles 10k Run Trail Virtual Walk

  Lexington, Kentucky, 40515, United States
  OpenStreetMap Google Maps
• Foundations 4 Hope 5K - Kentucky [runsignup.com]
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  Sat, Oct 03, 2026 at 8:00 AM

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  Foundations For Hope 5K- October 3, 2026 8:00 am

  • Chipped Time Event

  • Run or Walk 5K

  • Fun For All

  • Jerry Can 5K Relay - will be a (3) person relay with both men's teams and women's teams welcome....

  Foundations For Hope 5K- October 3, 2026 8:00 am

  • Chipped Time Event

  • Run or Walk 5K

  • Fun For All

  • Jerry Can 5K Relay - will be a (3) person relay with both men's teams and women's teams welcome. Each team will run/walk the 5K with a Jerry can provided by Foundations 4 Hope. The Jerry can will be filled with 5 Gallons (42lbs) of water for men teams and 3 Gallons (25lbs) of water for women teams. Time results end when the Jerry Can carried by each team crosses the finish line. Each team will sign up for the race as single entry but will be responsible for forming their own (3) person teams. The Jerry can can be carried in any position desired but no straps or alternative methods/additions to the can will be permitted. All age athletes are welcomed!

  • Starts and Ends at Alltech Arena on the beautiful grounds of the Kentucky Horse Park!

  The goal of the Foundations for Hope 5K is to Advance the Gospel by empowering the local church, investing in individuals, providing critical resources, and equipping Christian leaders. This year’s 5K will support a combination of these efforts, through the local church in East Africa, by providing communities with Christian leaders, churches, clean water, and medicine. Join us for a great event and be part of a generation being changed by the love of Jesus.

  3.1 Miles 5k Run Walk

  4089 Iron Works Pike, Lexington, Kentucky, 40511, United States
  OpenStreetMap Google Maps
• Monster Mash & Dash 5K Glow Run [runsignup.com]
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  Sat, Oct 10, 2026 at 12:00 AM

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  Join us for the 4th Annual Monster Mash & Dash 5K Glow Run supporting direct services at Recovery Cafe Lexington

  SATURDAY, OCTOBER 10, 2026 *** 6:00PM (Trunk or Treat at 7:15PM) *** COLDSTREAM...

  Join us for the 4th Annual Monster Mash & Dash 5K Glow Run supporting direct services at Recovery Cafe Lexington

  SATURDAY, OCTOBER 10, 2026 *** 6:00PM (Trunk or Treat at 7:15PM) *** COLDSTREAM RESEACH PARK (Lexington)

  RACE FEATURES:

  • Scenic, flat/fast course at Coldstream Research Park

  • Commemative unisex sized T-shirts

  • Overall & Age Group Awards (5-year divisions)

  • 5K Run/Walk, 1 Mile Fun Walk (untimed), Kid's Dash & Virtual option

  • Music, food, fun and fellowship

  • Dress Up's encouraged! Prizes for the best dressed!

  • Social Teams to expand your race experience. We'll have a prize for the largest team!

  • Free Race Photos (Thanks Paul Martin Photography)

  • Trunk or Treat to follow the races & awards ceremony

  5K ROUTE MAP

  PACKET PICKUP Our only packet pickup will be at Coldstream Dog Park (race venue) on Saturday, October 10th from 4:30-6:00pm.

  Recovery Cafe Lexington is a peer-led, peer-run community space for individuals to build recovery relationships and find supportive resources. We aren’t the type of café that sells sandwiches or lattés; we're a gathering space for folks on a recovery journey and our allies. We celebrate every type and pathway of recovery (substance use, mental health, housing insecurity, and more). No matter the need, we have resources to help; whether you or someone you know is in long-term recovery or contemplating making a change. We invite anyone to attend a support group, a sober social event, or see a Recovery Coach who can help be a guide through unique challenges. A new life is waiting for you!

  OUR VISION To empower people in their own recovery with a welcoming community driven sanctuary to connect with one another, heal, feel accepted, loved, and worthy of success in their life.

  OUR GUIDING PRINCIPLES 1.Connect with divine Love in ourselves and others, 2. Show Respect 3. Cultivate Compassion, 4. Practice Forgiveness, 5. Encourage Growth, 6. Give Back

  The Monster Mash and Dash 5K Glow Run will support direct services at Recovery Cafe Lexington, including School for Recovery Learning Programs, Weekend Life-Enrichment Retreats, Sober-Social Events, and direct financial assistance to program participants.

  1 Miles 3.1 Miles 5k Run Virtual Walk

  Lexington, Kentucky, 40511, United States
  OpenStreetMap Google Maps
• The Running Pumpkin [runsignup.com]
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  Sat, Oct 17, 2026 at 9:00 AM

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  Gleaning Housing is hosting the second annual Running Pumpkin 5k. Bring a pumpkin or if you are feeling more festive dress in your best pumpkin costume. We will provide pumpkins for anyone that...

  Gleaning Housing is hosting the second annual Running Pumpkin 5k. Bring a pumpkin or if you are feeling more festive dress in your best pumpkin costume. We will provide pumpkins for anyone that donated $20 or more to Gleanings Housing. Gleanings is a nonprofit that builds affordable rental housing in Lexington, Ky.

  Snacks and drinks will provide for all race participants.

  All are welcome for a fun fall run/walk.

  5k Run Walk

  Coldstream Park/Legacy Trail, Lexington, Kentucky, 40511, United States
  OpenStreetMap Google Maps
• Miles For Medicine 5K Run/Walk [runsignup.com]
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  Sat, Oct 24, 2026 at 12:00 AM

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  Join us for the 3rd Annual Miles For Medicine 5K Run/Walk as we raise funds to support the University of Kentucky College of Medicine Salvation Army Clinic!

  Saturday, October 24, 2026 at 9:00am at...

  Join us for the 3rd Annual Miles For Medicine 5K Run/Walk as we raise funds to support the University of Kentucky College of Medicine Salvation Army Clinic!

  Saturday, October 24, 2026 at 9:00am at Coldstream Park in Northwest Lexington

  RACE FEATURES:

  • Flat/fast 5K route on the Legacy Trail through scenic Coldstream Park

  • Commemorative performance T-shirts (Men's, Women's, Youth sizes)

  • Awards for Top 3 M/F Overall and Top 3 M/F in 5-year age groups

  • DJ and Free Race Photos (Thanks Paul Martin Photography)

  • Social Teams to Expand/Enhance your Race Experience (Prize for the largest social team)

  • Chip timing for the 5K provided by RaceRise

  • 5K Run/Walk, 1 Mile Walk (untimed), Kid's Dash & Virtual Option

  • Food, fun and fellowship for a great cause!

  WHY WE RACE?

  Our race will support the University of Kentucky College of Medicine Salvation Army Clinic (SAC).

  The University of Kentucky College of Medicine Salvation Army Clinic (SAC) has been serving Lexington residents for free since 1986. The clinic is located in and treats residents of the Salvation Army women and children’s shelter. The clinic currently has twice weekly adult clinics, and monthly pediatric and ophthalmology clinics along with oral cancer screenings provided by ENT and free weekly tobacco cessation groups. We also help patients sign-up for insurance, get established with primary care and dental care, and connect them with other community resources. The clinic is fully run by medical students with the support of volunteer physicians, pharmacists, and pharmacy students. The mission of SAC is to allow students to get early clinical exposure by assuming a leadership role in improving the health and well-being of the underserved populations in Lexington and to increase awareness of the social determinants of health while providing free medical services. Without the service and

  leadership of our volunteers, we would not be able to operate the clinic. The Salvation Army Clinic is completely dependent on donations and grants. All monies raised will go towards the purchase of medications and supplies for the clinic.

  5K ROUTE

  PACKET PICKUP DETAILS - We are conducting our packet pickup on race morning (Saturday) from 7:30-8:45am at Coldstream Dog Park. Look for the orange/blue RaceRise tent on race day. Pickup for friends/family/team members is fine and encouraged. There is no advanced day PPU for this year's race.

  1 Miles 3.1 Miles 5k Run Trail Virtual Walk

  Lexington, Kentucky, 40511, United States
  OpenStreetMap Google Maps
• The Gobbler Half Marathon, 10K & 5K [runsignup.com]
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  Sun, Nov 22, 2026 at 12:00 AM

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  THANKSGIVING WILL NEVER BE THE SAME AGAIN!

  Join us for the 11th Annual Gobbler Half Marathon, 10K & 5K on Sunday, November 22, 2026, at 8:30am at Mereworth Farm in West Lexington. Earn your...

  THANKSGIVING WILL NEVER BE THE SAME AGAIN!

  Join us for the 11th Annual Gobbler Half Marathon, 10K & 5K on Sunday, November 22, 2026, at 8:30am at Mereworth Farm in West Lexington. Earn your Thanksgiving feast the following Thursday with a scenic Half Marathon, 10K, or 5K through beautiful bluegrass horse country.

  RACE FEATURES:

  • Scenic country course through horse country

  • Start/Finish on Mereworth Farm (Home of New Vocations Racehorse Adoption)

  • Finisher's medals for all 3 races

  • Commemorative long sleeved performance race shirts

  • DJ James Hummel/Freestyle Entertainment

  • Free Race Photos (Ruby Cline-Eaton and JA Laub Photography)

  • A distance for everyone --- Half Marathon, 10K, 5K and Virtual Option

  • Overall & Age Group Awards for all 3 races (5-year age divisions)

  • Berserker Brew Coffee & Hot Cocoa

  • Food, fun and fellowship for a great cause

  In addition to our in-person race, we are also providing a VIRTUAL OPTION for those who can't join us in person (or who are not ready for an in-person race). Those who register as a virtual participant can run/walk/hike their race on their own schedule and on their own course. Virtual participants will earn a commemorative shirt and finisher's medal. We will mail out virtual packets to those who live outside of the Central Kentucky area. The registration fee for the virtual race (any distance) is $45.

  Our race charitable beneficiaries will be New Vocations Racehorse Adoption. Read more about this worthy local charity below.

  Our scenic half marathon course will traverse through beautiful horse country and past a number of our horse farms.

  IMPORTANT NOTE: Because our race starts and finishes on a horse farm, dogs are not allowed in this race as their presence could disturb the horses.

  Commemorative long-sleeved shirts (men's/women's sized) are on a first come, first served basis. When you register if your size is not available, you can either select another size or "no shirt option" to SAVE $5.00. We will have a SHIRT SWAP immediately following the race for anyone who either did not receive a shirt or got a size that they would like to trade with another participant. If we have race no shows, their shirts will be available for swap following the race.

  There will be a 15 minute/mile (3:15 total time) pace limit imposed for the half marathon race per contract with the City of Lexington. Walkers and strollers are welcomed in the 10K and 5K races. No dogs are allowed.

  PACKET PICKUP - 3 ADVANCED OPPORTUNITIES TO PICKUP FOR YOU AND FRIENDS/FAMILY

  • Thursday, November 19th from 5-7pm at J&H Running Company (197 Moore Drive, Lexington, KY 40503)

  • Friday, November 20th from 4-6pm at J&H Running Company (197 Moore Drive, Lexington, KY 40503)

  • Saturday, November 21st from 1-4pm at J&H Running Company (197 Moore Drive, Lexington, KY 40503)

  There will also be limited race day PPU from 7:15-8:30am mostly designed for our out of town/out of state runners. This will be a Mereworth Farm our race venue.

  HALF MARATHON COURSE CLICK HERE

  10K COURSE CLICK HERE

  5K COURSE CLICK HERE

  VOLUNTEERING Please consider volunteering for our benefiting charities at this race (or having friends/family do so). Our race day shift generally runs from 6:30am-12:00pm. Once you sign up, we'll be in touch with you about more details, duties, etc...

  3.1 Miles 5k 6.2 Miles 10k 13.1 Miles Half Marathon Run Virtual Walk

  Lexington, Kentucky, 40511, United States
  OpenStreetMap Google Maps
• Pioneer Coaching [pioneerultraraces.com] [Register at runsignup.com]
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  Thu, Dec 31, 2026 at 12:00 AM

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  • We offer sessions by the hour, keeping the price fair for you.

  • Individualized plans and meeting notes that cover everything we talked about.

  • Race specific packages that include four sessions,...

  • We offer sessions by the hour, keeping the price fair for you.

  • Individualized plans and meeting notes that cover everything we talked about.

  • Race specific packages that include four sessions, and initial session, a session at the midway point of your training block, pre-race strategy meeting, and post-race debrief.

  • Corporate run coaching and corporate run events

  Scroll down to see a detailed breakdown of each of our services!

  Run

  1320 Gray Hawk Road, Lexington, Kentucky, 40502, United States
  OpenStreetMap Google Maps

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