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.  Also available on Saturday:  our Kentucky Arts & Crafts, a Kentucky Art Walk, and Cooking with Kentucky Wine Demonstrations featuring renowned local chefs.  The festival also includes a Kentucky Farm to Table Dinner (Thursday) Kentucky Equine & Wine Tours (Friday).


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.


Wilmore Arts and Crafts Festival

Wilmore Arts & Crafts Festival [1st Saturday in October]

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: 859.881.3820


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

Annual Circle of Giving Wreath Display and 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.