Upcoming Holidays & Highlights in Central Kentucky

This page will be dedicated to a rolling list of upcoming holidays and highlight days. Hoping that keeping it all on one page will make it easier to find & bookmark. For certain larger holidays, I’ll still make a big list post like I typically do, and I’ll link to that here when I do!

Yearly Fall 2026 Events Post

September 11 (9/11)

Toast to the First Responders, Military, & Veterans | Belle’s Cocktail House | 9/11, 9:11P

Honoring Dolly

Discover Dance with Dolly | Gatton Park | 9/11, 7P

Sing Your Brunch Off: Dolly Edition | The Cellar B&G | 9/19

Dolly Par-Tea | Olive’s Apron | 9/19

Lussi Brown Coffee Bar: Specialty Drinks, donating $1 to the Imagination Library | All September

Harvest Moon (9/26)

Harvest Moon Party | Harkness Edwards Vineyard (Winchester) | 9/25, 5P-8P

Harvest Moon Hike | Shaker Village of Pleasant Hill (Harrodsburg) | 9/26, 7:30P

Bourbon Heritage Month (September)

Bourbon by the Signs | Holly Hill Cooking Studio (Versailles) | 9/3 & 9, 6:30P

Kentucky Bourbon Festival | Bardstown, KY | 9/11-9/13

Bourbon & Beyond | Louisville, KY | 9/24-9/27

Fall Events

Versailles Twilight Festival | Downtown Versailles | 9/12, 12P-9P

Apple Festival | Evans Orchard | 9/12-9/13

AutumnFest | Bi-Water Farm (Georgetown) | 9/12-11/1

Fall Kick Off Festival | East Lexington Peddlers Mall | 9/13, 11A-5P

Paris Pumpkin Festival | Paris | 9/19, 9A-8P

Midway Fall Festival | Downtown Midway | 9/19-9/20

Fall for Fritz Farm | Fritz Farm | 9/20, 1P-6P

Pumpkin Roll Making Class | Harkness Edwards Vineyard (Winchester) | 9/20, 3:30P

Decorative Pumpkin Making Class | Harkness Edwards Vineyard (Winchester) | 9/25, 5P

Decorative Pumpkin Making Class | Harkness Edwards Vineyard (Winchester) | 9/26, 2:30P

Bluegrass Creative Fall Market | Lexington Green | 9/26-9/27

Harvest Fest | Shaker Village of Pleasant Hill (Harrodsburg) | 9/26-9/27

Happy Fall Y’all Festival | Middle Springs Farm (Paris) | 10/3, 10A-6P

South Elkhorn CC Fall Festival | South Elkhorn Christian Church | 10/10, 9A-4P

Turning of the Leaves Festival | Augusta | 10/10, 10A-5P

Pumpkin Festival | Wildside Winery (Versailles) | 10/10-10/11

Pumpkin Patch Classic | Tates Creek Golf Course | 10/11, 8:30A & 2P

MQotHR Fall Festival | Mary Queen of the Holy Rosary | 10/16-10/17

Halloween Cookie Decorating | Shaker Village of Pleasant Hill (Harrodsburg) | 10/17, 3P-5P

KY Guild of Artists & Craftsmen Fall Art Market | Kentucky Artisan Center (Berea) | 10/17-10/18

Dunbar Fall Festival | Dunbar Community Center | 10/23, 6P-8P

Ginkgo Galore Festival | Wilmore | 10/24

Pumpkin Carving | Raven Run Nature Sanctuary | 10/24, 1P

Vintage Market Days Fall Market | Alltech Arena | 11/6-11/8

Twilight Critters Hike: Fall Critters | Shaker Village of Pleasant Hill (Harrodsburg) | 11/14, 5:30P-7P

Oktoberfest

Oktoberfest | Chinkapin Brewing (Georgetown) | 9/18, 4P-11P

CTK Oktoberfest | Christ the King Cathedral | 9/18-9/19

Kentucky Oktoberfest | Downtown Harrodsburg | 9/18-9/19

Oktoberfest | Ethereal | 9/26, 12P-Cl

Parktoberfest | Ashland Henry Clay Estate | 10/3

Spooky Events

Hocus Pocus Cookie Class | Harkness Edwards Vineyard (Winchester) | 9/26, 12P

Haunted Hayrides & Bonfires | Eckert’s Orchard (Versailles) | 10/2-10/31, Fridays + Saturdays

Freaky Flicks: Hocus Pocus (1993) | Masterson Station Park | 10/2, 6:30P

Adventure Theatre: Wicked Witches Brew | Shaker Village of Pleasant Hill (Harrodsburg) | 10/2-10/4

Spirit Strolls | Shaker Village of Pleasant Hill (Harrodsburg) | 10/2-10/31, Fridays + Saturdays

Obscurious Market: Trick or Treat | The Showroom (Danville) | 10/3, 12P

Freaky Flicks: Beetlejuice, Beetlejuice | Cardinal Run Park North | 10/9, 6:30P

Pumpkin Carving | Hisle Farm Park | 10/10, 10A-11:30P

3rd Annual Woodland Triangle Witchfest | Woodland Triangle Shops | 10/17

Wicked Wines & High Spirits Festival | Logan Vineyards Winery (Harrodsburg) | 10/17

Halloween Art Market | Villainous | 10/17, 5P-9P

Carv’n Chip’n | McConnell Springs Park | 10/18, 1P

Shaker Trick or Treat | Shaker Village of Pleasant Hill (Harrodsburg) | 10/23-10/24, 4:30-7P

Scarefest | Central Bank Center | 10/23-10/25

Pumpkin Carving | Raven Run Nature Sanctuary | 10/24, 1P-2:30P

Witches & Wine Festival| Wildside Winery (Versailles) | 10/24-10/25

‘Mister E of Imagination: Tales of Edgar Allen Poe’ by the Lexington Children’s Theatre | Lexington Children’s Theatre | 10/24-25, 10/31

Halloween Variety Show & Festival | Downtown Lexington | 10/25, 4:30P

Lexington Thriller Parade | Downtown Lexington | 10/25, 6:30P

Jack-o-Lantern Trail | McConnell Springs Park | 10/27-10/30

Yappy Hour: Howl-O-Ween | Masterson Station Park | 10/28, 5:30P-7:30P

Samhain | Wildside Winery (Versailles) | 10/31, 12P-6P

Lexington Trick or Treat | City-Wide | 10/31, 6P-8P

Going Batty | Shaker Village of Pleasant Hill (Harrodsburg) | 10/31, 6:30P-8P

Pleasant Hill After Dark | Shaker Village of Pleasant Hill (Harrodsburg) | 11/6-11/14

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Fall 2026

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