No matter the time of year, we have something going on to celebrate the season in a unique way.  Check out our annual events below or scroll through our event calendar and schedule the right time to visit that just so happens to peak your interest.

Annual Events

400 Mile Yard Sale – US 68

Travel along US 68 for a yard sale like no other.  June 6-9, 2019

Asbury University Sports

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

Camp Nelson Civil War Days.

Discover the rich history of Camp Nelson with their annual Civil War Days.  Second weekend in September

International Color Run

Enjoy this fun and colorful 5K run through beautiful Wilmore in support of mission work.  5k race is Saturday, September 21, 2019 @ 9AM rain or shine.  The International Color Run is brought to you by both GO InterNational and Cornerstone International. These two organizations, in partnership, hope to promote the importance of missions and gain support from the community.

Winery Comedy Tour at First Vineyard - June 29

Nationally recognized comedians travel the country tasting local wine and making new fans in this new comedy circuit that brings quality comedy to folks for a fraction of what antiquated comedy clubs demand. Come out for a night of hilarious comedy and great local wines. This comedy tour takes top comedians who you’ve seen on TV and sends them out on the road to perform at wineries throughout the country. Find out which local wines pair best with hysterical laughter when The Winery Comedy Tour comes to your town.

Visit for more information and to get tickets

Gospel on the Green Music Series

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

2019 Dates:  June 14 & 28, July 12 & 26 and August 9 & 23

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 17-18, 2019.

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.  April 27, 2019.

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 8 – 13, 2019

Jessamine Fall Fest

Enjoy the fall festival of Jessamine in downtown Nicholasville.  Children activities, petting zoo, music, food trucks, crafts and more. September 28, 2019

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 will be June 14 & 15, 2019.

More Tales, Wilmore Storytelling Festival

Come to Wilmore and enjoy the 3rd annual More Tales, Wilmore Storytelling Festival. This year features Kim Weitkamp, Stephen Hollen and Tim Lowry, just a few renown storytellers that will grace the stage.  There will also be food and craft vendors. So come enjoy a weekend of stories, food, fun and crafts.  September 20-21, 2019

Nicholasville’s Farmers Markets

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

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 18-21, 2019.

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 14, 2019.

Spooky Time on Main – Nicholasville

Bring the kids to the Trick or Treat Halloween festivities.

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.  2019 Dates:  June 15 & 29, July 13 & 27, and August 10 & 24

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 10, 2019

Treats on Main – Wilmore

Bring the kids to the Trick or Treat Halloween festivities.

VisitJessamine Bowl

August 23, 2019 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.  This year’s Coaster Car Derby will be April 27, 2019.

Wilmore’s Craft Fair

Wilmore opens the streets to art and craft vendors in conjuction with the Asbury Alumni Weekend.  October 5, 2019

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 7, 2019

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 9, 2019.

Paint the Town Banner - June 27, 2019

The 2019 Paint the Town Banner Event will be held on Thursday, June 27th 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.

Community Calendar


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