Annual Events are listed below. For a more complete list of events, visit our Calendar.

women tasting wine

The Kentucky Wine & Vine Fest [May]

Join us on the second Saturday of May at the Kentucky Wine & Vine Fest as we showcase vineyards and wineries from across the state. While you browse the winery booths, listen to live music and enjoy Kentucky Proud food products.

Phone:  859-887-4351                    Website:

Camp Nelson CemeteryCamp Nelson National Cemetery Memorial Day Commemoration [Memorial Day]

Annual ceremony to honor the memory of the veterans of this nation.

Phone: 859-885-5727


400 Mile Sale [First weekend in June from Thursday to Sunday]

Dozens of communities, hundreds of yard sales, antique shops, food vendors and fundraisers participate in this annual 4-day event at Servant-Heart Farm on US 68 in Wilmore.

Phone: 859-858-4411

Wilmore Fourth of July

4th of July Festival [1st Saturday in July]

For a 4th of July experience that will make you feel as if you’ve stepped back in time to the days when a walk down Main Street was “the bee’s knees,” visit the Wilmore 4th of July Festival.

Phone: 859-858-4411

Summer 2012 Willow and Sophia 093

Stonebridge Concert Series [Saturdays in July and August]

Free concerts with music ranging from Dixieland and the Blues to Southern Rock, Swing, and even contemporary and pop music. Chairs and tables are provided; refreshments for purchase from a local food vendor. Visitors may also bring their own blankets, chairs and snacks.

Phone: 859-858-4411

Jessamine County Fair [Mid July]

The Jessamine County Fair is held annually in Nicholasville, Kentucky at the Fairgrounds. Features include: FFA, 4H and FCCLA, Beef and Dairy Shows, Truck and Tractor Events, Pet Shows, a Demolition Derby, Pageants, and much, much more!

Phone: 859-885-3112
Website: Bowl [Mid-August]

Annual high school football invitational and soccerama.



High Bridge Homecoming Festival [3rd full weekend in August]

Free weekend-long festival with live music, dance, storytelling, arts, crafts, children’s activities, KY River boat tours, historical displays and local history/river museum, raffles, silent auction, dessert auction and more.

Phone: 859-858-3895

sneak peak shot

Camp Nelson Civil War Days [2nd weekend in September]

Annual Camp Nelson Civil War Days Living History Event on the grounds of the best-preserved Union Army supply depot and African American recruitment site in the nation — the 525-acre Camp Nelson Civil War Heritage Park. Military re-enactors perform infantry and artillery demonstrations with cannon firing throughout both days. First-person interpretations of soldiers and civilians, presentations, tours, period music, archaeological dig and more.

Phone: 859-881-5716 

Wilmore Arts and Crafts Festival

More Tales:  Wilmore’s Story Telling Festival, and Wilmore Arts & Crafts Festival [1st Saturday in October]

Join us for a storytelling competition,”spine tingling tales, ” by master storytellers, and more during Wilmore’s Storytelling Festival; during Wilmore’s Arts & Crafts Festival, approximately 50 vendors offer fine artist work and hand-crafted items such as stained glass, jewelry, hand carved and other wood items. A cake auction during the event benefits the Wilmore – Highbridge Community Service Center. Live music throughout the day.

Phone: 859-858-4411


Spooky Time on Main Street in Nicholasville [October]

Trick or Treating, children’s activities in historic downtown Nicholasville.

Phone: 859-885-4500


County Holiday Kick-Off [1st Weekend in December]

Join us for our Annual Tree Lighting Ceremony. Pictures with Santa, live music and performances by several local organizations.

Phone: 859-885-4500

Click to visit photo gallery.

For regular updates and information on Jessamine County tourism locations, like “Destination Jessamine” on Facebook.