MAY EVENTS: Local Events We ❤

Local events we LOVE this month

Events in Central Kentucky - May 2017

The month of May in Central Kentucky features everything from farmer’s markets to Mayfest to LOTS of Memorial Day/weekend celebration events….and so much more! 

Tea Tuesday at WavelandTea Tuesday at Waveland

May 2 @ 2:00 pm 3:30 pm

Waveland State Historic Site: 225 Waveland Museum Lane Lexington, KY 40514
Tea is served in the mansion on fine china. All tea’s include a program, savory food and is served by period dress interpreters. Once finished with the tea, enjoy a tour of the Waveland Mansion. Reservations are required.

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Big Band and Jazz Concert Series

Big Band & Jazz 2017

Every Tuesday May 2 @ 7:00 pm8:30 pm

MoonDance at Midnight Pass Amphitheatre: 1152 Monarch Street Lexington, KY 40513

Big Band & Jazz, one of Lexington’s longest running and most beloved concert series, features great jazz and big band music weekly.  The May and June concerts will be held at Moondance at Midnight Pass Amphitheatre in Beaumont Circle.  Bring your lawn chairs or blankets for seating. 

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Intercollegiate Horse Show Association National Championships

May 4 @ 8:00 amMay 7 @ 5:00 pmKY Horse Park: 4089 Iron Works Parkway Lexington, KY 40511

The 2017 IHSA National Championships will take place at the Alltech Arena. IHSA promotes competition for full time student riders of all skill levels, who compete individually and as teams at regional to national levels based on the principle that any college student should be able to participate in horse shows regardless of financial status, gender or riding level. Find out more » 



Central Bank Thursday Night Live

Central Bank Presents Thursday Night Live


Each Thursday @ 5:00 pm8:00 pm

Cheapside Park Fifth Third Bank Pavilion: 251 West Main Street Lexington, KY 40507

Beverages, food from local restaurants and great music by live bands! Every Thursday through October 12th. Find out more »



Oaks Day Party

Oaks Day Party @ Keeneland


May 5

Keeneland: 4201 Versailles Road Lexington, KY 40510 

FRIDAY, MAY 5 – OAKS DAY Watch and wager on the Kentucky Oaks at Keeneland! General admission and parking are free. Gates open at 9:00 a.m. ET. Patrons are permitted to picnic inside the grandstand area for this event. Tents, canopies, grills and glass are not permitted in the Paddock, Walking Ring or North Terrace. Patrons are not permitted to bring alcohol. Coolers are allowed, but are subject to inspection. Pets are not allowed. Find out more »


KY Derby at Keeneland

Kentucky Derby Party @ Keeneland

May 6

Keeneland: 4201 Versailles Road Lexington, KY 40510

Festivities include live music, pony rides, food and wagering! Known as the largest Derby party in the world!  Don’t miss the world’s biggest Derby Party! With over 1,000 televisions, easy access to wagering, great food, activities for the kids and more, Derby Day at Keeneland is the perfect place to view the Run for the Roses. Details: Gates open at 9:00 a.m. Patrons are permitted to picnic inside the grandstand area for this event. Tents, canopies, grills and glass are…  Find out more »


Sleeping Beauty with the Russian National Ballet Theatre

May 7 @ 3:00 pm5:00 pm

EKU Center for the Arts1 Hall Drive Richmond, KY 40475

Direct from Moscow! An enchanted romantic fairy tale for all ages, the Russian National Ballet Theatre brings Sleeping Beauty to life through this ballet perfect for the entire family. With a timeless score by Tchaikovsky, the ballet captures the delight, fantasy, and drama of this cherished story. With its roots in the Bolshoi, the Russian National Ballet remains a standard bearer for the traditions and majesty of classic Russian ballet.   Tickets: … Find out more »


Wine and Vine Fest

The Kentucky Wine & Vine Fest

May 11May 13

Downtown Nicholasville, 996 North Main Street Nicholasville, KY

About the Event Picture it:  It’s the 2nd Saturday in May, and you and your friends are sipping and savoring your way through the booths of over a dozen Kentucky wineries, including Jean Farris Winery, Talon Winery, and Elk Creek Vineyards –-all at the 2017 Kentucky Wine & Vine Fest.  The festival, held in historic downtown Nicholasville (home of First Vineyard, the first commercial vineyard in the United States) and Chrisman Mill Vineyard,  is designed to celebrate all of the wonderful things that make the…  Find out more »

Peter Pan

Peter Pan w/ KY Ballet Theatre

May 12May 13

Lexington Opera House, 401 West Short Street Lexington, KY 40507

Mother’s Day weekend will never be the same as Peter and Wendy fly across the stage (literally!) by ZFx Flying during this beautiful story. Indians, lost boys, tinker bell and of course, Peter will whisk you away to Never Never Land where Captain Hook and the pirates offer hilarious obstacles for Peter and his companions. Presented by The Kentucky Ballet Theatre.  Details Dates: Friday, May 12, 2017 – Saturday, May 13, 2017 Times:Friday 7:00 p.m. and Saturday 2:00 p.m. and…Find out more »



MayFest Arts Fair 2017

May 13May 14

Gratz Park, 251 West 2nd Street Lexington, KY 40507

Mayfest is a juried art fair with a focus on casual, family-friendly atmosphere.  Included are up to 100 Artist Vendors, Young Artists, Demonstrating Artists and Activity Artists, performances by musicians, dancers, strolling performers and children’s activities.  Details Dates: Saturday, May 13, 2017 – Sunday, May 14, 2017 Times:Saturday 10:00 AM – 6:00 PM, Sunday 11:00 AM – 5:00 PM Location:Gratz Park & Transylvania Admission:FREE Find out more »

John’s Run Local 8K

May 13 @ 8:00 am12:00 pm

KY Horse Park, 4089 Iron Works Parkway Lexington, KY 40511

The run honors and commemorates John Sensenig’s 40 years of service to the local running community. John has been a fixture in the local running and walking community since opening his first local running shop in 1977. John’s Run Local 8k has grown from the desire to celebrate all he has given to the local Lexington and Central Kentucky community.   Join us at the beautiful Kentucky Horse Park on May 13, 2017 to honor and commemorate John Sensenig’s 40…Find out more »

Fishing Derby

May 13 @ 9:00 am12:00 pm

Jacobson Park, 4001 Athens-Boonesboro Road Lexington, KY 40509

The Union Sportsmen’s Alliance and Kentucky American Water invite you to bring the kids out for a fun day of fishing for trout and catfish. The first 200 kids will receive a free fishing rod, reel, tackle and tackle box. Instruction and assistance will be available. Kids age 15 and younger do not need a fishing license. Older youth and adults can purchase a 1-day fishing license for $7 at All youth must be accompanied by an adult.  Find out more »

Southland Street Fair

May 13 @ 3:00 pm8:00 pm

Southland Neighborhood, Southland Drive Lexington, KY

The whole family is invited out to one of Lexington’s hottest and most eclectic neighborhood to enjoy music, food, kids activities and a chance to support local businesses. #SouthlandStreetFair  Find out more »

Bluegrass Classic Stockdog Trials

May 17May 21

Masterson Station Park, 3051 Leestown Road Lexington, KY 40511

The famous Bluegrass Classic Stockdog Trial will once again be held at Lexington’s Masterson Station Park on May 17-21, 2017, marking 55 years of border collie trials in the Bluegrass. This competition is one of the longest-running, largest, and most prestigious trials in the country. The competition draws top handlers from across the USA and Canada, as well as hundreds of local spectators. The Bluegrass Classic dates from at least 1960, and was held for many years at Walnut Hall…Find out more »

Kentucky Sheep and Fiber Festival

May 20May 21

Masterson Station Park, 3051 Leestown Road Lexington, KY 40511

This year’s 8th annual festival exists to bring together the arts and crafts community with the producers of the fibers they utilize. With over 100 vendors each year, live animals, sheep shearing demonstrations and an amazing array of classes – the festival has something for everyone!  Details Saturday 9:00 a.m.-5:00 p.m. & Sunday 10:00 a.m.-4:00 p.m. Location:Masterson Station Park Admission:$5 out more »


RJ Corman 5k Run/Walk for Chrysalis House

May 20 @ 9:00 am5:00 pm

RJ Corman Hangar, 101 RJ Corman Drive Nicholasville, KY 

Prize money for top 3 male and female finishers. Post-race lunch prepared by My Old Kentucky Dinner Train Executive Chef. This is a completed closed course on the grounds of RJ Corman. Children’s activities. Register online. Proceeds benefit Chrysalis House. Find out more »


Vintage Market Days: Home Sweet Home


May 26May 28

KY Horse Park, 4089 Iron Works Parkway Lexington, KY 40511 


Vintage Market Days® is an upscale vintage-inspired indoor/outdoor market featuring original art, antiques, clothing, jewelry, handmade treasures, home décor, outdoor furnishings, consumable yummies, seasonal plantings and a little more. Vintage Market Days® events are so much more than a flea market. Each Vintage Market Days® event is a unique opportunity for vendors to display their talents and passions in creative venues. An upscale, vintage-inspired indoor/outdoor market featuring original art, antiques, clothing, jewelry, handmade treasures, home décor, outdoor furnishings, consumable yummies,…  Find out more »


2 thoughts on “MAY EVENTS: Local Events We ❤

  1. Very impressive! I really enjoyed reading each…..
    So colorful and eye catching! Frances Hall recently
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    should impress most people,

    1. We are so glad Frances was able to help you with your real estate needs. She is a FANTASTIC agent and we are so honored that she works with us. We hope that she and Rector Hayden can continue serving you with any of your home ownership wants and needs!

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