Cycling in Lexington, Kentucky | 2026-2027

Reforest Frenzy [runsignup.com]
Sat, Mar 21, 2026 at 8:00 AM

Description

Run with us to help Reforest the Bluegrass!

John’s Bluegrass Racing Company, ASICS & Lexington’s Division of Environmental Services are excited to present the seventh annual Reforest Frenzy at Hisle...

Run with us to help Reforest the Bluegrass!

John’s Bluegrass Racing Company, ASICS & Lexington’s Division of Environmental Services are excited to present the seventh annual Reforest Frenzy at Hisle Farm Park. Race proceeds will help raise money to purchase trees for this year’s Reforest the Bluegrass in April. With your help, we hope to plant hundreds of trees after the race at home and thousands more during Reforest the Bluegrass.

All race participants will receive a Reforest Frenzy shirt, and the option to take a tree to plant at home after their run or walk.

Overall Awards for Top 3 Male & Female in each distance.

Packet Pickup:

Thursday 3/19: 10am - 8pm @ John's Run/Walk Shop 317 S. Ashland Ave, Lexington KY 40502

Friday 3/20: 10am - 8pm @ John's Run/Walk Shop 317 S. Ashland Ave, Lexington KY 40502

Race Day pick up at Race HQ @ Hisle Farm Park 7am - 8am.

Sustainability:

Reforest the Bluegrass is an annual event at which volunteers of all ages get together for a fun day of tree planting that leaves a lasting positive imprint on our Commonwealth. Since 1999, Reforest the Bluegrass has enabled more than 18,000 volunteers to plant 215,000 tree seedlings across Central Kentucky.

John’s Run/Walk Shop is committed to helping protect the ground we run and walk on and the air we breathe. In addition to putting on the Reforest Frenzy we engage in local sustainability efforts in many other ways. We are a Green Check-certified business. We offer our stores as drop-off points for the City of Lexington to collect yard signs and holiday lights for recycling, and we take used shoes to refurbish or recycle through Sneaker Impact.

We’re excited to partner with ASICS for this race, as they are working toward a net-zero 2050 target. ASICS has set several targets and actions, involving the increased use of renewable energy and overall reduction in energy use in their operations.

Course Map

1 Miles 5k 10k Cycling Run Walk
3551 Briar Hill Rd, Lexington, Kentucky, 40516, United States
OpenStreetMap Google Maps

Freebird 5K [runsignup.com]
Sat, Sep 12, 2026 at 12:00 AM
Description
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]
Sun, Sep 13, 2026 at 7:45 AM

Description

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]
Thu, Sep 24, 2026 at 2:00 PM

Description

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

4 cycling events in Lexington, Kentucky

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Local Clubs & Organizations