No matter the time of year, our community is buzzing with events and activities for the whole family. Flashback to the days of radio with a live performance “broadcast” hosted by the KCAL Old Time Radio Troupe or hear a Chautauqua reenactor recount the story of local historical figure, Jemima Boone at the Jessamine County Library. Search for artifacts with the archaeologists at Camp Nelson National Monument, attend our summer concert series to fill your evening with the sweet sounds of local Kentucky music, or sample all the finest Kentucky-crafted vintages at the Wine & Vine Festival. Visit our event calendar below to find out which events coincide with your visit to Jessamine County. We’ll see you there!

Annual Events

400 Mile Yard Sale – US 68

Travel along US 68 for a yard sale like no other.  This year’s dates have been changed to October 2, 3 & 4, 2020 due to COVID-19.  

Asbury University Sports

Let’s go Eagles!  No matter the season, Asbury always has a great game to catch!

Dinner & Show - Old Time Radio Troop @ First Vineyard

The Old Time Radio Troupe’s performance has been postponed until August 8 (everything else remains the same). If you have already purchased tickets, please call KCAL’s box office at 859-885-5363 as soon as possible to let them know if you still want to attend on August 8.
First Vineyard is so glad to once again be hosting the Jessamine County Old Time Radio Troupe, who will be performing the 1940 classic comedy My Favorite Wife, as a staged radio broadcast, on Saturday, May 9, 2020. The dinner, which is optional, will be catered by Judy Gurnee Catering, and will consist of Sliced Pork Loin with Bourbon-Spiked Bacon and Red Onion Sauce; Garlic Linguini Parmigiana (linguini, spinach, caramelized onion, and garlic in creamy sauce) (Side Dish or Vegetarian Entrée); Rosemary Roasted Potatoes with Butter, Mixed Greens Salad with Garden Vegetables and Choice of Dressings; Homemade Yeast Rolls; Shaker Lemon Pound Cake with Wild Blackberry Sauce or Chocolate Cobbler with Whipped Cream; Iced Tea or Citrus Water. Wine will be available for purchase.
To purchase your ticket(s) or for more information, please call the KCAL box office at 859 885-5363. Seating is limited so please call asap!
Dinner 6:00 – 7:00 ($17.50)
Show 7:30 – 8:30 ($10.00)
Dinner & Show $27.50

Gospel on the Green Music Series

Gospel on the Green Music Series takes place in Wilmore, KY on Friday evenings during the summer.

2020 Dates:  

Highbridge Film Festival

The Highbridge Film Festival is the largest event on Asbury’s campus each year…other than graduation. It is sold out year-after-year. It showcases high school and Asbury University student films. Highbridge is dedicated to expressing and exploring the human condition through the power of the visual story.  

Highbridge Film Festival will be going virtual this year! Come and join us on April 25, 2020 at 7:00 PM (EDT)!
The virtual link will be posted later.

High Bridge Homecoming Festival

Enjoy the beauty of High Bridge Park at the annual High Bridge Homecoming Festival.  Antique tractors, cars, craft and food vendors as well as local musicians such as our very own Moron Brothers will truly entertain at this great event.  August 15-16, 2020

Jessamine County Fair

It’s the annual county fair!  From funnel cakes, cotton candy, pageants, mud runs, livestock show and carnival rides, there’s so much to enjoy! July 6 – 11, 2020

Jessamine Fall Fest

Enjoy the fall festival of Jessamine in downtown Nicholasville.  Children activities, petting zoo, music, food trucks, crafts and more. September 25-26, 2020

Kentucky Wine & Vine Fest

Kentucky’s premiere wine event celebrating not only wineries here in Jessamine but across the whole bluegrass state.  This year’s Wine&Vine has been rescheduled for Saturday, August 29.  

More Tales, Wilmore Storytelling Festival

Come to Wilmore and enjoy the 4th annual More Tales, Wilmore Storytelling Festival.  There will also be food and craft vendors. So come enjoy a weekend of stories, food, fun and crafts.  September 18-19, 2020

Nicholasville’s Farmers Markets

Open Every Saturday now May thru October 9 am – 1 p, 717 North Main Street Nicholasville, Kentucky

Paint the Town Banner -

The Paint the Town Banner Event will be held  at the Blue Building at City/County Park in Nicholasville. This community art project brings together all ages and talents to create colorful banners for Nicholasville’s Main Street. Painting times are 9:00 am and 2:00 pm. Participant applications available at the Jessamine County Courthouse, 101 North Main Street in Nicholasville. There are a limited number of spots available and applications are on a first come basis. For more information, please contact Justin Ray at 859-533-5184 or the County Judge’s Office at 859-885-4500. Special thanks to Goff Tents & Events.

PGA’s Barbasol Championship

Enjoy the PGA’s very own Barbasol Championship at Keene Trace.  Did you know that the PGA will host this event in Nicholasville through 2023?  There’s plenty of time to book your tickets and watch some of golf’s best athletes here in the bluegrass state.  July 16-19, 2020.

Saint Nich Fest & Parade

Enjoy the spirit of Christmas in downtown Nicholasville, Kentucky.  The Saint Nich Fest offers craft vendors, food trucks, kettle corn, lights and of course the annual Christmas parade.  December 19, 2020.

Spooky Time on Main – Nicholasville

Bring the kids to the Trick or Treat Halloween festivities.  October 31, 2020

Stonebridge Concert Series

On Saturday evenings in Wilmore during the summer, this concert series features a variety of music: jazz, bluegrass, big band, folk, Dixieland, etc.  Event starts at 7pm.  

Taste of Jessamine

Who doesn’t enjoy some good food and company?  The annual Taste of Jessamine features a wide variety of delicious foods and treats brought to you by the locals of Jessamine.  Sponsored by First Southern National Bank, this event takes place at the RJ Corman Hanger directly off US 27 in Nicholasville, May 8, 2020

Treats on Main – Wilmore

Bring the kids to the Trick or Treat Halloween festivities.  October 31, 2020.  

VisitJessamine Bowl

Enjoy the bowl game hosted by VisitJessamine as our two local teams of East & West Jessamine High invite other teams in a fun football and soccer tournament.

Wilmore’s Coaster Car Derby

Enjoy Main Street in Wilmore and watch the coaster cars race down the street in this fun event in the spring.  

Wilmore’s Craft Fair

Wilmore opens the streets to art and craft vendors in conjuction with the Asbury Alumni Weekend.  October 3, 2020

Wilmore’s Farmers Markets

Wilmore’s Farmers Market takes place every Saturday from May to the end of September.  Located at 339 East Main Street, Wilmore, KY 40390 from 8am to Noon.

Wilmore’s Old Fashioned Christmas

Explore the streets of Wilmore with open houses, official tree lighting and musical concert.  This event takes place the first Saturday in December.  December 5, 2020

Wilmore’s Veteran’s Day Parade

Celebrate the veterans the Saturday morning before Veteran’s Day Parade.  This year the event will take place November 7, 2020.

Community Calendar


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