Explore Winchester

Happening Next in Winchester

Upcoming Events in Winchester

Christmas at Aisling House: Victorian Christmas Tea

Aisling House 20 Nov 2026
HOLIDAY USD 157

Christmas at Aisling House: Christmas Brunch

Aisling House 6 Dec 2026
FITNESS USD 145

Christmas at Aisling House: Open House

Aisling House 6 Dec 2026
FITNESS USD 45

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

Aisling House 31 Dec 2026
FITNESS USD 482

Build Your Stack with Bluegrass Silver Co

21 S Main St, Winchester, KY, United States, Kentucky 40391 14 Nov 2026

The Nook After Dark

2 S Main St, Suite 200, Winchester, KY, United States, Kentucky 40391 21 Nov 2026
ENTERTAINMENT

Pumpkin Painting

36 N Highland St., Winchester, KY 21 Nov 2026
ART

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

Aisling House 31 Dec 2026
FITNESS USD 21,338

🦃 EVERYTHING BUT THE TURKEY BINGO! 🦃

30 Beckner St, Winchester, KY 40391-1810, United States 13 Nov 2026
BINGO

I am Financially Free: Family Wealth & Wellness Experience

2745 Boonesboro Rd, Winchester, KY 40391-9291, United States 21 Nov 2026
HEALTH-WELLNESS

Ladies’ Night

36 N Highland St., Winchester, KY 14 Nov 2026
ART

WWKY Radio Chamber After Hours

Boone House Grill 11 Nov 2026

Author Signing Olivia Mcintyre

2 S Main St, Suite 200, Winchester, KY, United States, Kentucky 40391 14 Nov 2026
ART

One More Round is coming to Winchester Elks Lodge

Winchester Elks Lodge # 2816 20 Nov 2026

Friendsgiving Chili Cook Off & Community Dinner

Emmanuel Episcopal Church 15 Nov 2026
THANKSGIVING

Downtown Holiday Pop-Up Shop

The Hall on Main Coffee and Cafe 14 Nov 2026
POP-UPS

Downtown Winchester Holiday Open House!

Main Street, Winchester, KY, United States, Kentucky 40391 13 Nov 2026
HOLIDAY

LunaLuxe Holiday Open House

LunaLuxe 5 Dec 2026
HOLIDAY FREE

Christmas at Aisling House: VIP Weekend Family Suite

Aisling House 5 Dec 2026
FITNESS USD 1,811
Browse by category

More things to do in Winchester