2026 Boonesborough Boogie Nationals

Fort Boonesborough Living History 9 Oct 2026

Winchester Pride + Inclusion Festival 2026

Depot St, Winchester, KY 40391, United States 3 Oct 2026

Clark Co Fall Demo Derby

Clark County Fair & Horse Show, Inc. 3 Oct 2026

Market to Main

32 Wall Street, 40391-1900 13 Jun 2026

Book Nook’s Fall Author Fest

66 S Main St. Winchester Ky 26 Sep 2026

Christmas at Aisling House: Victorian Christmas Tea

Aisling House 19 Nov 2026

Pig Pickin’ for the Past

Hollyrood 28 Beckner Street, Winchester, Ky 40391 26 Sep 2026

Survive or Thrive 26 - KENTUCKY

2661 Clintonville Rd, Winchester, KY 40391-8980, United States 9 Oct 2026

Halloween @ Old Habits

3685 Four Mile Road, Winchester, KY, USA 31 Oct 2026

Christmas at Aisling House: Christmas Brunch

Aisling House 6 Dec 2026

Practical Magic: A Night at the Cottage

55 S Main St, Winchester, KY, United States, Kentucky 40391 3 Oct 2026

3rd Annual Black Azz Camping Trip

Black Roots Farm 9 Oct 2026

Community Book Club w/ Rev. Ryan

5 Cleveland Avenue Ste 209 Winchester, KY 30 Sep 2026

New Year’s Eve at Aisling House: VIP Overnight Experience

Aisling House 31 Dec 2026

Christmas at Aisling House: Open House

Aisling House 6 Dec 2026

Vampire Ball

Whiskey and Wiles 30 Oct 2026

New Year’s Eve at Aisling House: The Black Tie Celebration

Aisling House 31 Dec 2026

Aerial Yoga Teacher Training

The Fly Witches 25 Sep 2026

The Red Moon Release Signing

2 S Main St, Suite 200, Winchester, KY 3 Oct 2026

TRU Challenge Festivus

4793 Suite A Rockwell Rd, Winchester, KY 10 Oct 2026