May 2020 Lexington Area Events

Oaks Day at Buffalo Trace | Frankfort May 1

Experience the excitement of Derby weekend with another Kentucky tradition: bourbon. Enjoy complimentary tours and tastings all day from 9:00a–4:30p. Enjoy live festive Bluegrass music, shopping, food and more while treating yourself to bourbon ice cream made with our Buffalo Trace Bourbon. For more information, click here.

Lillies in Lexington | Keeneland | May 1

Hosted by Easter Seals Cardinal Hill, from 3 – 7pm. For more information click here.

Fiber to Fabric | Fort Boonesborough | May 2

This is a hands on history event that teaches turning flax and wool into fabric including wool and flax preparation, spinning, and weaving on period looms. For more information go to

Derby Day in Lexington | Keeneland | May 2

H’ARTFUL OF FUN | Living Arts & Science Center | May 9, 7 – 11pm

A dazzling celebration of art and science education! Join us at the place where creativity grows for a magical evening of food, friends and fun. Enjoy Lexington’s best art auction, live and silent auctions, live music, dinner and spirits and artful surprises.

Dancing with the Lexington Stars| Marriott Griffin Gate | May 9

Lexington Heart Walk | Keeneland | May 9

Taste of the Bluegrass | Keeneland | May 15

Neon Night Run | Downtown Richmond | May 22

The streets of downtown Richmond come to life with color at this fun, family friendly run/walk to increase cancer awareness in our community. Join us for the inaugural Neon Night Run on Friday, May 22, 2020 at 9 p.m. in Downtown Richmond. This Paint the Town Pink event will include commemorative T-shirts, glow medals for all finishers, overall awards, music, food, fun and fellowship. Register today for the early bird discount at

Horsey Hundred | Georgetown | May 22 – 24

The Horsey Hundred is the signature ride of the Bluegrass Cycling Club. The Horsey Hundred is held annually on Memorial Day weekend and draws thousands. For more information visit the event website.

Big Lex 4 Miler | May 23 | Race Rise, Lexington 8 – 10 am

Join us for the race that celebrates all that is great about Lexington!
The 2nd Annual BIG LEX 4 Miler on Saturday, May 23, 2020 at 8:00am at historic Keeneland Race Course. This is the 1st leg of the 2020 Bluegrass Trifecta Race Series.

The Big Lex will officially kick off summer in the Bluegrass. Our race will feature commemorative race shirts (Men’s and Women’s sizes available), a unique 4 mile race course through the historic Keeneland grounds, an exciting team competition, overall and age group awards, post race massage, DJ James Hummel (Freestyle Entertainment) and an awesome post race celebration.

Spring Trade Days | Fort Boonesborough | May 23

Visit a gathering of merchants, traders, artisans, Native Americans, longhunters, scouts and other frontier characters. Listen to period music as you visit the camps and shop. For more information go to