May 2019 | Lexington Area Events


Kentucky Baseball vs. UARK | Lexington | May 3

Come watch UKY Baseball take on University of Arkansas at Kentucky Proud Park at 6:30pm. Jersey Tote Bag Giveaway.

Kentucky Oaks Day Party – Lillies in Lexington | Keeneland | May 3

Keeneland Room, 3:00 p.m. – 7:00 p.m.

Celebrate Kentucky Oaks Day in the beautiful Keeneland Room, adjacent to the outdoor terrace overlooking the track!

  • Heavy Hors D’Oeuvres
  • Two Drink Tickets, Cash Bar
  • Live Simulcasting of all races from Churchill Downs
  • In-Room Wagering for both Oaks Day & Derby Day Races
  • Handicapping Seminars, Keeneland Betologist!
  • Bourbon Tastings
  • Behind the Scenes Keeneland Tour
  • Live Music in Keeneland Paddock: 4:00pm—6:00pm

Backstretch Tour | Keeneland | May 3

Join us for a look at Thoroughbred racing at its finest. Begin your day on the backside with a walk through the barns to see raceday preparations underway. Other tour stops include a trackside view of morning workouts, the racing office and restricted Jockey’s Quarters. For more information visit Keeneland’s website.


Pushing the Envelope – Mail Art | UK Art Museum | Opens May 3

Pushing the Envelope is drawn from collections of the Smithsonian’s Archives of American Art and was curated by Miriam Kienle, a University of Kentucky assistant professor of art history, in conjunction with students in her special topics seminar on the international mail art movement. Click here for more information.


May 4 & 5, 11 & 12 | Ward Hall Tours |Georgetown


Governor’s Downtown Derby Celebration | Frankfort | May 4

Governor and First Lady Bevin cordially invite all Kentuckians and their guests to join them at the Governor’s Downtown Derby Celebration on May 4th from 9:00 a.m. until 1:00 p.m. in downtown Frankfort. 

The 2019 Derby Celebration will showcase Frankfort with new and traditional festivities for which the Governor’s Derby Celebration is known—offering plenty of color, excitement, entertainment, children’s activities, and food to suit all tastes.  >>Read More


Mayfest Arts Fair | Lexington | May 11-12

In it’s 25th year, Mayfest is a visual, performing and literary arts fair that takes place annually on Mother’s Day weekend, in historic Gratz Park. The festival includes a variety of juried art and craft vendors from around the state and country

Iron Stomachs and White Knuckles Presentation | Lexington | May 11

On Saturday May 11, Mike Braasch visits the Aviation Museum of Kentucky from the Ohio University Avionics Engineering Center. His presentation “Iron Stomachs and White Knuckles: 56 Years of Navigation Flight Testing” tells the story of the Engineering Center’s experiences over the years. This program will have a special start time of 3 pm.                       


My Old Kentucky Dinner Train’s Murder Mystery | Bardstown | May 11

We invite you to join us on board for a memorable journey that’s sure to keep you guessing. While riding through Kentucky’s scenic countryside, guests will enjoy a four course meal and a live murder mystery show! The events lasts approximately two and a half hours and will thrill the young and young at heart. Tickets are $109.95 for adults and $69.95 for children (5-12). The excursion begins at 5:00 p.m. at the Train Depot. Reservations recommended. 602 N Third St., 502-348-7300 or 866-801-3463.

Bulegrass River Run 2019 | May 11

This spring grab a kayak, paddle board, or canoe and join EKI & friends for the third annual Bluegrass River Run (BRR) presented by Visit Lex, one of the largest paddling events in Kentucky. We’ll launch from Fort Boonesborough State Park paddling along pool 9 of the Kentucky River, which is located just south of Lexington. The journey allows you to take in the incredible beauty of the 60+ ft cliffs of the palisades, musical artists playing from docks along the river, and the camaraderie of floating with people from all across the country. For more information, visit the event page.


Hands on Workshops | Berea | May 11 & 12

The HOW program gives visitors a chance to learn more from master craftspeople and artists such as glass blowing, jewelry making, fiber arts, sustainable living, blacksmithing and many more. For more information or to register, go to or call 800-598-5263.


My Old Kentucky Dinner Train’s Mother’s Day Excursion | Bardstown | May 12

Mother’s Day is our standard three course lunch with a specific surprise for all the mothers. Tickets are $69.95 for adults and $44.95 for children (5-12). 602 N Third St. 11:30 a.m. Reservations required. 502-3487300 or 866-801-3463.

Farmer to Table Dinner | Blue Grass Stockyards | May 16


B-17 “Aluminum Overcast” at Aviation Museum of KY | Lexington | May 16 – 19

Scheduled to stop by the Aviation Museum of Kentucky May 16-19 is the B-17 “Aluminum Overcast” from the Experimental Aircraft Association. WW II bombers are a big attraction at the museum, and the B-17 will be available for ground tours and for flights.


Alice in Wonderland Story Circle | Ashland – Henry Clay Estate – Lexington | May 18

The circle of stumps under the Catalpa is a lovely setting for Story Circles. Three Story Circles include snack, gift, and a unique photo opportunity. Our first Story Circle will be Alice in Wonderland themed and will be at 10:00 am on May 18th. Weather permitting, we’ll gather at the Story Circle for our snack and reading, then characters from Alice will be in the formal garden for a photo opportunity.  For more information visit the event page.

My Old Kentucky Dinner Train’s Bourbon Excursion | Bardstown | May 18

Relax while you enjoy a 2½ hour excursion through the beautiful Central Kentucky countryside, a gourmet four-course meal, a tasting of bourbon hosted by a master distiller and a souvenir rocks glass. All guests must be 21 years and older. 5:00 p.m. Reservations required. $109.95 per adult. 602 N Third St., 502-3487300 or 866-801-3463.

Kentucky Railway Museum’s Train Robbery | Bardstown | May 18

Join us for a wild ride as your train gets robbed by a gang of train robbers! Train departs at 2 p.m. Train ride is approximately 2 hours. You will be robbed! Proceeds benefit the Crusade for Children. Adults: $21.00 Children $16.00 (ages 2-12) under 2 is free.136 S. Main St., New Haven. 502-549-5470 or 800-272-0152.

Sidewalk Sale | Georgetown | May 18

To kick off the much-anticipated summer, we are happy to present this year’s first Sidewalk Sale on Saturday, May 18! Shop all day in Downtown Georgetown for special discounts & promotions from participating businesses. Whether it’s a new pair of shorts or flip-flops, we have just what you need at our annual Sidewalk Sale! 


Flight Simulator Sunday at Aviation Museum of KY | Lexington | May 19

Try your hand at flight on one of the flight simulators at the Aviation Museum of Kentucky. Offered the third Sunday of the month from 1:30 – 4:30. Included with the cost of admission.


Split Rock Jumping Tour | Lexington | May 22 – 26

Along with watching the highest level of Show Jumping, spectators will have access to a variety of boutiques, food vendors, children/family activities, and live music.

Horsey Hundred Bicycling Event | Georgetown & Surrounding Area | May 24 – 26

Horsey Hundred is a leading central Kentucky cycling event sponsored by the Bluegrass Cycle Club. This event takes place on Memorial Day Weekend and features 30, 50, 66 & 100 mile rides in areas surrounding Georgetown, Kentucky. The Horsey 100 welcomes over 2200 cyclists from all over the country and internationally for road cycling and southern hospitality. Rides begin on the campus of Georgetown College and continue across Kentucky’s most scenic countryside. Riders travel through quaint historic towns and along backroads bordering some of the world’s most famous horse farms.

Friday Night Block Party | Versailles | May 24

Friday Night Block Party brought to you by the City of Versailles and the Versailles Merchant Association. Enjoy live music, food and drink vendors and activities for the whole family! There will be dancing at this family-friendly event! Held on W. Green St.

Longhorn Sale | Bluegrass Stockyards | May 24 – 25

Art in the Park | Versailles | May 24 – 25

Enjoy seeing and purchasing the amazing work of artists and craftspeople at the 11th annual Art in the Park events. There is something for everyone from jewelry, pottery, quilts, floral, wood and more. 104 Park St., Versailles

Party in the Park | Georgetown | May 25

Celebrate summertime with live music, food and drinks during Georgetown, KY’s Party in the Park concert series. Downtown Georgetown’s Royal Spring Park invites the public on Saturday, May 25 for a fun and free evening featuring local artist Danny Brook. The party starts at 7pm and ends when the crowd goes quiet. For more information, visit or contact Georgetown/Scott County Tourism at 502-863-2547. Royal Spring Park

My Old Kentucky Dinner Train’s Murder Mystery | Bardstown | May 25

We invite you to join us on board for a memorable journey that’s sure to keep you guessing. While riding through Kentucky’s scenic countryside, guests will enjoy a four course meal and a live murder mystery show! The events lasts approximately two and a half hours and will thrill the young and young at heart. Tickets are $109.95 for adults and $69.95 for children (5-12). The excursion begins at 5:00 p.m. at the Train Depot. Reservations recommended. 602 N Third St., 502-348-7300 or 866-801-3463.

Whiskey City Cruisers | Bardstown | May 25

Stroll among classic cars from yesteryear. Fourth Saturday of the month April-October. Kentucky Home Square shopping center. 2 p.m. – dusk. 502-348-6456 or 800-638-4877.

Chamber Music Festival of the Bluegrass | Harrodsburg | May 25 – 26

Spend the weekend with world-acclaimed chamber musicians from New York’s Chamber Music Society of Lincoln Center. Special performances in the Meadow View Barn at 11am and 5pm. Enjoy educational lectures, exploring the history of each piece of music in the festival. Shaker Village of Pleasant Hill, Harrodsburg.


Frankfest | Frankfort | May 26

Kick off summer with live music, children & arts activities, a car cruise, and refreshments at Lakeview Parkon Sunday, May 26th! This event is free & everyone is welcome! Click here for specific event details.


Lexington Legends Baseball | Lexington | May 30 – June 2

Bring the whole family for a fun time at the ball park as the Legends host the Charleston RiverDogs featuring Saturday Night Fireworks. Whitaker Bank Ballpark.

Summer Concert Series 2019 | Bardstown | May 31

Free weekly band concert series featuring a wide variety of musical styles, from bluegrass to jazz, to classic rock, to country and Sousa. 7 – 9 p.m. at Bardstown Community Park. (In the event of rain, concert will be held at the Farmers Market on East Flaget Ave.) 502-348-4877 or 800-638-4877.


Vintage Market Days | KY Horse Park | May 31 – June 2

This upscale vintage inspired indoor/outdoor market features original art, antiques, clothing, jewelry, handmade treasures, home decor, outdoor furnishings, consumable yummies, live music, food trucks and more. Covered Arena at the Kentucky Horse Park.