The Holidays in Central Kentucky 2025
Events
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Holiday Market & Visits with Santa | The Evergreen (Frankfort) | 11/1, 9A-1P
Christmas Bazaar & Breakfast | St. Leo School (Versailles) | 11/1, 9A-2P
Harvesting the Holidays | Harrison Square (Cynthiana) | 11/1, 10A-4P
Winter Art Market | Midway Art Studios | 11/1, 11A-6P
Holiday Card Making | Sparky’s Tinkery (Georgetown) | 11/1, 1P
Wake Up Santa! | Fayette Mall | 11/5, 5:30P
November Holiday Tour Lunch | The Kentucky Castle | 11/6, 20; 11A + 12P
Holiday Open House | Syers Browning | 11/5-11/9
Christmas Open House | Tunies | 11/6-11/8
Holiday Classes | Various Locations | 11/8
7P | Green Monster Rug | Craft-Tucky (Nicholasville)Christmas Open House Weekend | Ada & Lo | 11/7-11/9
Christmas Open House Cocktail Party | Ada & Lo | 11/7, 5P-7P
Christmas Sweet Treats & Sneak Peeks | My Darling & Co, Skin Boutique, Kristen’s Kreations (Versailles) | 11/7, 5P-8P
Thanksgiving Trivia Night | Boone’s Trace Grill (Richmond) | 11/7, 7P-9P
Christmas Past & Present Holiday Open Houses | Downtown Cynthiana | 11/7-11/8
Holiday Classes | Various Locations | 11/8
10A | Holiday Reed Stars | Shaker Village (Harrodsburg)
11A | Autumn Arrangement | Pinot’s Palette
2P | Holiday Reed Stars | Shaker Village (Harrodsburg)
2P | Watercolor Holiday Cards | A Likely Story (Midway)Central KY Bookstore Crawl: Holiday Hop | Various Locations | 11/8, 9A
Pumpkin Collection | Stonewall Elementary School | 11/8, 9A-12P
Holiday Market | Sadieville Farmer’s Market | 11/8, 9A-1P
Titan Holiday Craft & Vendor Fair | Royal Springs Middle School (Georgetown) | 11/8, 9A-3P
Holiday Marketplace | Providence Christian Church (Nicholasville) | 11/8, 9A-3P
Holiday Craft Bazaar | Central Baptist Church (Lawrenceburg) | 11/8, 9A-3P
Mercer 4-H Holiday One Stop Shop | The Stable at Mercer Co Fairgrounds (Harrodsburg) | 11/8, 9A-3P
5th Annual Sip & Shop | Coldwell Banker McMahan (Winchester) | 11/8, 10A-3P
Shimmer & Shine Craft Fair | Porter Memorial Baptist Church | 11/8, 10A-3P
Midway Old Fashioned Christmas Kick-Off | Downtown Midway | 11/8, 10A-4P
Gingerbread Land Holiday Open House | Em + Me Collective (Georgetown) | 11/8, 15; 10A-4P
Holiday Launch | Tiny Bird Books (Versailles) | 11/8, 10A-4P
Christmas Market | Shaker Village (Harrodsburg) | 11/8, 10A-5P
Holiday Classes | Various Locations | 11/9
1P | The Green Monster Tree | Craft-Tucky (Nicholasville)
2P | Holiday Doormat Class | Chenault Vineyards (Richmond)
3:30P | Pumpkin Floral Design | Lexington Tea & Brie
4P | Let It Snow Light Up Lean To | Craft-Tucky (Nicholasville)Pour for a Purpose: Thanksgiving Wine Market | The Willow | 11/9, 12P-4P
November Holiday Tour Dinner | The Kentucky Castle | 11/7, 11; 4:30P + 5:30P
November Holiday Tour Dinner | The Kentucky Castle | 11/11, 4:30P + 5:30P
Holiday Classes | Various Locations | 11/12
Carved Pumpkin Floral Arranging | Poppy’s Flower BarCandlelight at the Old State Capitol | Old State Capitol (Frankfort) | 11/13, 5P-8P
Jake’s Annual Friendsgiving | Jake’s Cigar Bar (Nicholasville) | 11/13, 7P
Candlelight Weekend | Downtown Frankfort | 11/13-11/15
Holiday Open Houses | 11/13-11/15
Frances M
Peggy’s Gifts
The Hidden Trove (Georgetown)Holiday Sip & Shop | Christ the King School | 11/14, 4P-9P
CASA Giving Tree Madison County | Dreaming Creek Brewery (Richmond) | 11/14, 5:30P-7:30P
Fall & Christmas Market | Grace Freewill Baptist Church | 11/14-11/15
22nd Annual Hope for the Holidays | Paul Miller Mazda | 11/14-11/15
Holiday Greenery Helpers | Shaker Village (Harrodsburg) | 11/14-11/15
Christmas Bazaar & Luncheon | St. Andrew Catholic Church (Harrodsburg) | 11/14-11/15
Holiday Market | The Kentucky Castle | 11/14-11/16
‘A Christmas Carol’ Radio Show | Rohs Opera House (Cynthiana) | 11/14-11/16
Holiday Classes | Various Locations | 11/15
11A | Turkey Lurkey | Painting with a Twist
1P | Stained Glass Angels | Art & Alley (Lawrenceburg)
2:30P | Holiday Doormat Painting | Harkness Edwards Vineyards (Winchester)
7P | Frosted Forest | Pinot’s PaletteHoliday Market | Harrison County Farmer’s Market (Cynthiana) | 11/15, 9A-3P
Holiday Barn Market | Hawk’s Nest Weddings (Winchester) | 11/15, 10A-2P
Versailles Merchant Association Christmas Open Houses | Various Locations (Versailles) | 11/15, 10A-4P
Gingerbread Land Holiday Open House | Em + Me Collective (Georgetown) | 11/15, 10A-4P
Holiday Open House | Room Service | 11/15, 10A-4P
KY Pop Ups Holiday Market | Fayette Mall Lot | 11/15, 11A-4P
Friendsgiving Sip & Shop | Girls Just Wanna Have Fun (Richmond) | 11/15, 12P
The Polar Express PJ Party | Grand Theatre (Frankfort) | 11/15, 3P
Capitol Christmas Tree Whistlestop Tour | 11/15, 5P-7P
Midway Old Fashioned Christmas Gallery Hop ‘n Shop | Downtown Midway | 11/15, 5P-8P
Friendsgiving Fundraiser | The Void Sake Co | 11/15, 7P
Bluegrass Creative Holiday Market | Lexington Green | 11/15-11/16
Annual Holiday Open House | Subject Matter | 11/15-11/16
Pre-Holiday PAUSE Wellness Retreat | Shaker Village (Harrodsburg) | 11/15-11/17
Holiday Classes | Various Locations | 11/16
Holiday Charcuterie Tree | Harkness Edwards Vineyards (Winchester)
2P | Always Jolly Rustic Santa | Painting with a Twist
2P | Watercolor Holiday Cars | Prodigy Vineyard (Frankfort)
3P | HoHoHo Lean-To | Craft-Tucky (Nicholasville)Christmas Tea Party | The Mousetrap | 11/16, 4P
Greensgiving | Neighborhood Farmacy Market (Both Locations | 11/19, 2P-7P
Thanksgiving Murder Mystery Dinner | Chenault Vineyards (Richmond) | 11/19, 6:30P-8:30P
November Holiday Lunch | The Kentucky Castle | 11/20, 11A + 12P
Glass Class: Ornaments & Christmas Trees | Fayette County Extension Office | 11/20, 1P & 5P
Thanksgiving Tasting | Paddock Bourbon Club | 11/20, 7P
‘A Christmas Carol’ by The Lexington Theatre Company | Lexington Opera House | 11/20-11/23
Holiday Classes | Various Locations | 11/21
6P | Thanksgiving Wine & Design | Georgetown Flowers & Gifts
6:30P | Snowy Stargazing Painting | Pinot’s Palette
7P | Christmas Tree Cake Door Hangers | Craft-Tucky (Nicholasville)Pink Friday | 11/21
Pink Friday Celebration | Downtown Versailles
Gifts, Sales, Bargain Bins, etc | Boutique on Maple at 721 (Nicholasville)
Gifts & Drawings | Pink Market Boutique (Georgetown)
Pirie BoutiqueEnd of Fall Market | The Void Sake Co. | 11/21, 5P-10P
Light Up Lawrenceburg | Anderson Co. Middle School (Lawrenceburg) | 11/21, 6P
Holiday Open House (Santa + Tree Lighting) | Lexington Green Shopping Center | 11/21, 6P-8P
Christmas Bazaar | Eastminster Presbyterian Church | 11/21-11/22
Holiday Mixmas Market | The Manchester Reserve | 11/21-11/22
Christmas Open House | Southern Lux Style | 11/21-11/23
Annual Winter Encampment | Old Fort Harrod State Park (Harrodsburg) | 11/21-11/23
Turkey Etouffee Season | Bourbon & Toulouse | 11/21-26
Holiday Classes | Various Locations | 11/22
10A | Holiday Reed Stars | Shaker Village (Harrodsburg)
11A | Friendsgiving Focaccia | Midway Art Studios
11A | Crazy Reindeer Painting | Painting with a Twist
11A | Winter Wreath Painting | Pinot’s Palette
1P | Cornhusk Angels | Shaker Village (Harrodsburg)
2P | Peppermint Jar Centerpiece | Craft-Tucky (Nicholasville)
3P | Farmhouse Frosty Painting | Painting with a Twist
3P | Holiday Tree Painting | Harkness Edwards Vineyards (Winchester)
4P | Ornament Painting Fundraiser | Elements Clay (Lawrenceburg)
7P | Holiday Pick Up Painting | Painting with a TwistYouth Turkey Run | Castlewood Community Center | 11/22, 9A-11A
Christmas Market | Seton Catholic School | 11/22, 9A-1P
Family Class: Holiday Card Making | The Living Arts & Science Center | 11/22, 10A-12P
Christmas Vendor Market | Local Roots KY (Winchester) | 11/22, 10A-4P
Turkey Trot Fun Run | Huntertown Park (Versailles) | 11/22, 11A
United Vendors Holiday Fair | Immanuel Baptist Church | 11/22, 11A-3P
$20 Holiday Art Market | Greyline Station | 11/22, 11A-3P
Cranksgiving | Broke Spoke | 11/22, 12P
Holiday Market | PKL Lex | 11/22, 1P-5P
Friendsgiving Holiday Tea | Lexington Tea & Brie | 11/22, 3:30P-5:30P
Southern Lights Stroll | The KY Horse Park | 11/22, 5:30P
Christmas Tree Lighting | Old Fort Harrod State Park (Harrosdsburg) | 11/22, 6P
Ravesgiving Party | Neon Nights | 11/22, 8:30P
Friendsgiving Latin Dance Social | El Jefe | 11/22, 9P-12A
Holiday Classes | Various Locations | 11/23
2P | Merry Macrame Ornaments | Mick’s Pot Shop
2P | Holiday Barn Painting | Painting with a Twist
3P | Merry Christmas Door Hanger | Craft-Tucky (Nicholasville)
5:30P | Holiday Paint Your Pet | Painting with a TwistKY Pop-Ups Holiday Market | Regal Cinemas Lot (Hamburg) | 11/23, 12P-5P
Back Alley Book Swap: Holiday TBR Edition | Tiny Bird Books (Versailles) | 11/23, 2P
Tidings of Comfort & Calm: A Holiday Self Care Workshop | Lexington Salt Cave | 11/23, 4P-5:30P
Annual 2nd District Tree Lighting & Toy Drive | Lexington Fire Station No. 24 | 11/23, 2P-4P
Trash Movie Monday: Thanksgiving Edition | Arcadium | 11/24, 7:30P
Holiday Classes | Various Locations | 11/25
Thanksgiving Floral Centerpiece | Poppy’s Flower BarHick’s & Funfsinn’s 5th Annual Tunes for Toys | The Burl | 11/26, 6P
The Night Before Thanksgiving Show | Comedy Off Broadway | 11/26, 7P
Holiday Classes | 11/28
7P | A Very Van Gogh Christmas | Pinot’s Palette
7P | Sea Glass Christmas Tree | Craft-Tucky (Nicholasville)
7:30P | Blacklight Christmas Tree | Painting with a TwistSnake Cake Day | West Sixth Brewing (All Locations | 11/28
Gobble Grease Toss | Redwood Cooperative School | 11/28, 10A-2P
Pappy Thanksgiving benefiting Operation Secret Santa | Chevy Chase Inn | 11/28, 12P
Soul Stuffing Friendsgiving ft. Magnolia Boulevard | The Burl | 11/28, 8P
The Kentucky Shop BF Sip & Shop | Manchester Music Hall | 11/28-11/29
Festival of Trees + Craft Fair | Oleika Shriners Temple | 11/28-30
Holiday Classes | Various Locations | 11/29
10A | Vintage Paper Creations | Shaker Village (Harrodsburg)
12P | Ornament Wreath Class | Harkness Edwards Vineyards (Winchester)
2P | Vintage Paper Creations | Shaker Village (Harrodsburg)Blessing of the House | Shaker Village (Harrodsburg) | 11/29, 9A-11A
SBS Christmas Market | Depot Street (Winchester) | 11/29, 10A
Meet Black Santa | North Lime Donuts | 11/29, 10A-12P
Midway Old Fashioned Christmas: Santa Arrives by Train | Downtown Midway | 11/29, 10A-1P
A Kentucky Christmas | Hamburg Pavilion | 11/29, 10A-2P
SBS Market | Pinnacle Neighborhood Clubhouse | 11/29, 10A-3P
Annual Holiday Barn Market | Chenault Vineyards (Richmond) | 11/29, 10A-6P
Annual Shop Small Market | Chaotic Goods CCG | 11/29, 11A-4P
Lexington Art League Holiday Market | The Loudon House | 11/29, 12P-6P
Hancock and Shouse Bluegrass Christmas | Louis Flower Power Shop | 11/29, 12:30P-1:30P
Holiday Market | Cecily’s Hair Studio | 11/29, 1P-5P
Meet Black Santa | BK’s Cookies & More | 11/29, 2P-4P
Festival of Living Windows | Downtown Versailles | 11/29, 12/13; 5P-7P
Brunch with Santa | The Kentucky Castle | 11/30
Holiday Market Art & Craft Fair | Unitarian Universalist Church of Lexington | 11/30, 10A-2P
Feral Folk Art Market | Greyline Station | 11/30, 11A-4P
Art on the Town Holiday Market | Tandy Park | 11/30, 11A-4P
Paws 4 the Cause Winter Festival | Paws 4 the Cause | 11/30, 12P-4P
Sounds of the Season presented by the Lexington Chamber Chorale | Second Presbyterian Church | 11/30, 5P
Holiday Classes | Various Locations | 12/3
Floral Christmas Wreaths | Poppy’s Flower Bar‘Rudolph the Red Nosed Reindeer, Jr.’ | Lexington Children’s Theatre | 11/30-12/8
Christmas Shoppe in the Cottage | Ashland Henry Clay Estate | 12/1-12/6
‘It’s a Wonderful Life’ by BCTC Theatre | Pam Miller DAC | 12/4-12/6
Holiday Classes | 12/5
5P-8P | Winter Snowflake | ImpactLex
5:30P-7P | Glass Ornaments | CreatedByYou Ceramic Studio (Winchester)Versailles Tree Lighting | Downtown Versailles | 12/5, 5:30P
Jessamine Co. Christmas Tree Lighting | Jessamine Co. Courthouse (Nicholasville) | 12/5, 6P
Black Santa & The Lexington Singers in the Winter Village | Gatton Park | 12/5, 6P-7:30P
LexArts: Crafting with a Queen | LexArts Artsplace | 12/5, 6P-8P
GNO: Christmas Edition | ELITE Fitness | 12/5, 6P-9P
Jingle & Mingle | Joseph-Beth Booksellers | 12/5, 6P-10P
Nutcracker Christmas Parade | Downtown Harrodsburg | 12/5, 6:30P
Salsa Night: Winter Ski Party | The Salsa Center | 12/5, 7:30P-10:30P
Crafted Social Winter Market | Greyline Station | 12/5-12/6
‘It’s A Wonderful Life’ by the Leeds Center | Leeds Center for the Arts (Winchester) | 12/5-12/7, 12/11-12/14
Holiday Classes | 12/6
9:30A | Holiday Ornament Carving | McConnell Springs
9:30A | Melty Snowman Ornaments | Elements Clay Studio (Lawrenceburg)
10A | Santa Mug Candles | Midway Art Studio
10A-2P | Ornament Class | ImpactLex
11A-1P | Holiday Nature Ornaments | Raven Run
12P-2P | Holiday Wreaths | Harkness Edards (Winchester)
2P | Christmas Cookies | Bleubird Studio (Georgetown)
2P | Eco-Ornaments | Shaker Village (Harrodsburg)
2:30P | Freestyle Holiday Paint | Painting with a Twist
3P | Holiday Cookie Decorating | Shaker Village (Harrodsburg)Holiday Open Houses | 12/6
8A-4P | Martine’s Pastries
9A-4P | Cakes by Bebe (Wilmore)
9A-4P | Shades of Bluegrass (Wilmore)
10A-4P| Lexington Visitor’s Center
10A-7P | Shaker Village Shops (Harrodsburg)Lexington Holiday Celebration | Downtown Lexington | 12/6
10A | Candy Cane Corner Opens
10A, 10:25A | Children’s Holiday Readings | The Greenery
11A | Parade
12:30P | Post-Parade Elf Screening | Lex LiveCandlelight Tours | Ashland, Henry Clay Estate | 12/6, 12, 14
Let’s Get Lit Christmas Party | girlsgirlsgirls Burritos | 12/6
’A Charlie Chaplin Christmas’ by Lexington Ballet | Lyric Theatre | 12/6
WCCFM Christmas Market | Clark Co Farmer’s Market (Winchester) | 12/6, 8A-12P
Santa Open House | Martine’s Pastries | 12/6, 8A-4P
Wilmore’s Old Fashioned Musical Christmas | 12/6, 8:30A-8P
8:30A-3P | Craft Fair | Wilmore Municipal Center
9A-4P | Main Street Market | Downtown Wilmore
1P-3P | Asbury Equine Journey to Bethlehem | Asbury Equine Center
2P | American Songs & Carols | Wilmore Methodist Church
5:30P | Tree Lighting | Med-Save
5:45P-7:45P | Main Street Stroll | Downtown Wilmore
8P | Grand Finale Seasonal SingingUrban Village’s Christmas Market | Wilmore Presbyterian Church | 12/6, 9A-3P
2nd Annual Christmas on the Farm | BraveHearts Equine Center (Paris) | 12/6, 10A
Pancakes with Santa | Morning Pointe | 12/6, 10A-12P
Christmas Bazaar | Jack Kain Ford (Versailles) | 12/6, 10A-2:30P
Jingle Jamboree | Posh Affairs (Georgetown) | 12/6, 10A-3P
Winter Wonderland | City Limits (Nicholasville) | 12/6, 10A-4P
Holiday Market at The Well | Cherry Well Farm (Winchester) | 12/6, 10A-4P
Children’s Tea Time with Mrs. Claus | Shaker Village (Harrodsburg) | 12/6, 13, 20; 11A
Storytime with Black Santa | Barnes & Noble | 12/6, 11A-1P
Jingle Bell Bazaar | The Boutique at Merle Norman (Richmond) | 12/6, 11A-3P
Christmas Market | Georgetown Church of the Nazarene | 12/6, 11A-4P
Winter Extravaganza | Aging with Grace | 12/6, 12P-2P
Meet Biker Santa + The Grinch | Harley Davidson MoW | 12/6, 12P-3P
Holiday Gift Bottle Engraving: Maker’s Mark | Jackson’s Wine & Spirits | 12/6, 12P-4P
Deck the Halls with RMHC | Ronald McDonald House | 12/6, 12P-4P
Winter Soiree | Sorelle Aesthetics (Winchester) | 12/6, 12P-4P
Deck the Paws Crafternoon wth BBR | Ethereal Brewing | 12/6, 1P-4P
Holiday Market | Lavender in Bloom (Georgetown) | 12/6, 1P-5P
Peppermint Ball | The Ballroom House | 12/6, 1:30P-9P
Santa Visits LSC | Lexington SC Stadium | 12/6, 2P
Sugar Plum Run 5K | Downtown Versailles | 12/6, 2P
Meet Black Santa | TMobile (Richmond Rd) | 12/6, 2P-4P
The Maiden Christmas Market | Downtown Cynthiana | 12/6, 2P-7P
Holiday Highlights Tour | KY Old State Capitol (Frankfort) | 12/6, 13, 20; 3P-3:30P
Rockin’ Recovery Holiday Jam | Event Vibes | 12/6, 3P-7P
TubaChristmas | Joseph-Beth Booksellers | 12/6, 4P
A Kentucky Christmas Tree Lighting | Ashland, Henry Clay Estate | 12/6, 4P-6P
Illuminated Evenings | Shaker Village (Harrodsburg) | 12/6, 13, 20; 4P-8P
A Wonderful Woodford Christmas Parade | Downtown Versailles | 12/6, 5P
Krampus Art Market | Villainous | 12/6, 5P-10P
Paris-Bourbon Co. Christmas Parade + Tree Lighting | Paris | 12/6, 5:30P
Home for the Holidays Christmas Celebration | Downtown Georgetown | 12/6, 6P
LCT Holiday Heroes | Lexington Opera House | 12/6, 6P-6:45P
Stilt Walkers & Jugglers in the Winter Village | Gatton Park | 12/6, 6P-7:30P
Improv Bingo: Holiday Edition | The Spot Comedy Cub | 12/6, 7P
Argo Lynn Holiday Show | Chinkapin Brewing (Georgetown) | 12/6, 7P
Toy Drive for the Nest Benefit Show | The Cellar Bar & Grill | 12/6, 7P-11P
Winter Wonderland Pageant | The Bar Complex | 12/6, 8:30P
Holly Day Market | Alltech Arena (KY Horse Park) | 12/6-12/7
Princess Party | 12/6, 12P-1:30PBreakfast with the Grinch | Joseph-Beth Booksellers | 12/6-12/7, 9A
‘Holmes for the Holidays’ by the LexCath Theater | Lexington Catholic High School | 12/6-12/7
‘The Nutcracker’ on Ice | Lexington Ice Center | 12/6-12/7
LCT’s ‘Rudolph the Red-Nosed Reindeer’ | Lexington Opera House | 12/6-12/7
Holiday Craft & Vendor Fair | Mary Queen of the Holy Rosary School | 12/6-12/7
Christmas Market | Michler’s | 12/6-12/7
Collage: A Holiday Spectacular | UK’s Singletary Center | 12/6-12/7
Holiday Shop Hop | Woodland Triangle | 12/6-12/7
Christmas Market Fest | Wildside Winery (Versailles) | 12/6-12/7
Holiday Afternoon Tea | Shaker Village (Harrodsburg) | 12/6-12, Saturday + Sunday, 3P
2025 Gingerbread Showcase | Shaker Village (Harrodsburg) | 12/6-12/20
Holiday Classes | 12/7
1P | Holiday Focaccia | Harkness Edwards (Winchester)
1P-3P | Sea Glass Christmas Tree | Craft-Tucky (Nicholasville)
1:30P-8:30P | Freestyle Holiday Paints | Painting with a Teist
3:30P | Mini Holiday Pies | Harkness Edwards (Winchester)Brunch with the Grinch | Good Foods Co-Op | 12/7, 10A-2P
Brunch with Santa | Rackhouse Tavern | 12/7, 10A-2P
Annual McDaniel Memorial Choral Presentation: ‘Five Carols’ | Central Christian Church | 12/7, 11A
Holiday Drag Extravaganza | Tin Roof | 12/7, 11A
How the Bitch Stole Christmas Drag Brunch | The Void Sake Co. | 12/7, 11A
Breakfast with Santa | Carson’s | 12/7, 14; 11A-2P
Cookies & Cocoa Brunch with Santa | Boone Trace Bar & grill (Richmond) | 12/7, 11A-3P
Holiday Brunch at the Distillery | Woodford Reserve (Versailles) | 12/7, 14; 11:15A
Santa Visit | The Annex at Mirror Twin | 12/7, 12P-3P
Christmas Winter Vendor Market | 209 Events (Georgetown) | 12/7, 12P-4P
3rd Annual Hanukkah Market | Greyline Station | 12/7, 1P-4P
Santa Fly-In | Aviation Museum | 12/7, 2P
Enrich Christmas Tea | Enrich (Richmond) | 12/7, 3P-5P
Slay Bells 2025 | Lyric Theatre | 12/7, 5P-10P
A Very Merry Christmas Dinner | Fasig-Tipton | 12/7, 5:30P
A Charlie Brown Christmas & Duke Ellington’s Nutcracker Suite | The Kentucky Theatre | 12/7, 5:30P
2025 Winter Choral Concert by Scott Co & Great Crossing HSs | UK’s Singletary Center | 12/8, 7P
Holiday Dinner Tour | The Kentucky Caslte | 12/9
Holiday Horns! | UK’s Singletary Center | 12/9, 6P-8P
‘BAJA’s Jazzy Christmas XXI’ presented by UK Jazz Studies | UK’s Singletary Center | 12/9, 7:30P
Holiday Wine Classics Class | The Willow | 12/10, 6:30P
Over the Rhine Holiday Concert | The Kentucky Theatre | 12/10, 7:30P
Holiday Classes | Various Locations | 12/11
Christmas Tree Centerpiece | Poppy’s Flower BarHoliday Open Houses | Various Locations | 12/11
Bombshell Salon | 11A-8POrnament Exchange + Tree Decorating Party | Institute 193 | 12/11, 5P-7P
Santa Arrives by Helicopter | Fritz Farm | 12/11, 6P-8P
Holiday on the Hill | Heaven Hill (Bardstown) | 12/11, 6P-9P
Santa Trains | Bluegrass Railroad Museum (Versailles) | 11/29-12/14, Saturdays + Sundays
Oh Come Let Us Adore Him: A Celebration of Nativities from Around the World | Gardenside Christian Church | 12/10-12/12, 10A-12P & 5P-8P
‘It’s A Wonderful Life’ by the Leeds Center | Leeds Center for the Arts (Winchester) | 12/11-12/14
Candlelight Tours | Ashland, Henry Clay Estate | 12/12, 14
Holiday Showings: ‘The Nightmare Before Christmas | The Kentucky Theatre | 12/12, 14, 15
Reindeer Express Event | The Nest | 12/12, 9A-4P
Museum Holiday Party | Hopewell Museum (Paris) | 12/12, 5:30P
Jingle Jam | First United Methodist Church | 12/12, 6P-8P
Annual Ugly Sweater Party | Dreaming Creek Brewery (Richmond) | 12/12, 6P-8:30P
A Second Chance Christmas | The Void Sake Co | 12/12, 6P-10P
Ugly Sweater Christmas Party + Toy Drive | Slainte Public House (Georgetown) | 12/12, 6P-10:30P
Holiday Folklore by the Fireside | Woodford County Library )Versailles) | 12/12, 6P-7:30P
2025 Central KY Dance Theatre Winter Gala featuring The Nutcracker Ballet | UK’s Singletary Center | 12/12, 7P
Murder Mystery Dinner: Twas the Murder Before Christmas | Equus Run (Midway) | 12/12, 7P
The Lexington Ringers in the Winter Village | Gatton Park | 12/12, 7P-7:30P
Cookie Swap | Darling Wine Bar | 12/12, 7P-9P
Sounds of Christmas: Addie & Cole | The Willow | 12/12, 7:30P-9:30P
Unofficial Hi 5 Christmas Party for Shriners Children’s Hospital | The Cellar Bar & Grill | 12/12, 8P
Ugly Sweater Holiday Party | The Ballroom House | 12/12, 8P-10P
Hollerday Gitdown with Nicholas Jamerson | The Burl | 12/12-12/13
‘The Nutcracker’ by United Fine Arts Academy | United Talent (Georgetown) | 12/12-12/14
Holiday Classes | Various Locations | 12/13
10A-12P | Holiday Wreath Making | UK’s Arboretum
10A | Eco-Ornaments | Shaker Village
10A | Reed Stars | Shaker Village
11A | Farmhouse Christmas Painting | Painting with a Twist
2P | Eco-Ornaments | Shaker Village
2:30P | Cookie Decorating | Harkness Edwards Vineyards (Winchester)
3:#0P | All I want for Christmas is Moo Painting | Pinot’s Palette
4P | Fused Glass Christmas Lantern | Createdbyyou Studio (Winchester)
7P | Festive Christmas Path | Painting with a TwistChristmas Cookie & Beer Pairing | Blue Stallion Brewing Co | 12/13
Holiday Showings: ‘Gremlins’ | The Kentucky Theatre | 12/13, 16
Jolly Jog 2.5 Miler | Feet Fleet | 12/13, 8A
Breakfast with Santa | Oleika Shriners | 12/13, 8A-11A
Shop with a Cop | Walmart (Georgetown) | 12/13, 9A
Pancakes with Santa | Forcht Bank (Hamburg) | 12/13, 9A-11A
Breakfast with Santa | STEAM Academy | 12/13, 9A-11A
Breakfast with Santa | Fayette Co Extension Office | 12/13, 9A-12P
Lexington Marker’s Market Holiday Markets | Greyline Station | 12/13, 20; 9A-1P
Christmas Market Vendor Fair | Grace Baptist Academy (Winchester) | 12/13, 9A-2P
2nd Annual Young Entrepreneurs Holiday Market | Classic Spaces (Georgetown) | 12/13, 9A-3P
Annual Vendor Fair | Coolidge Building (Nicholasville) | 12/13, 9A-4P
St. Nich Christmas Fest | Downtown Nicholasville | 12/13, 9A-4P
Christmas at the Coolidge Vendor Market | 9A-4P
Artisan Fair | JCPL | 10A-3P
Christmas Maker’s Market | The Oaks | 10A-5P
Gingerbread Contest | 12P-2P
Ugly Sweater 5K | 4:30P
Parade | 5:30PThe Toy Chest’s Elf Workshop | Talon Winery | 12/13, 9A-5P
Reindeer Ramble 5K | Keeneland Race Track | 12/13, 10A
Holiday History Hike | Camp Nelson National Monument (Nicholasville) | 12/13, 10A-2P
Brunch with Santa | Merrick Inn | 12/13, 10A-2P
Holiday Vendor Market | Northside Elementary School (Midway) | 12/13, 10A-3P
Old Fashioned Christmas Shop & Stroll | Downtown Midway | 12/13, 10A-5P
‘A Christmas Story’ Special Screening benefiting The Nest | The KY Theatre | 12/13, 10:30A
Holiday Social | Houstondale (Paris) | 12/13, 11A + 3P
Midway Santa Shuffle 5K | Downtown Midway | 12/13, 11A
Children’s Tea Time with Mrs. Claus | Shaker Village (Harrodsburg) | 12/13, 20; 11A
Jarrett’s Joycart Toy Drive | Clarks Pump N Shop (Lucille Dr) | 12/13, 11A-1P
Richmond Area Arts Council Holiday Festival | Richmond Shopping Centre | 12/13, 11A-2P
Gingerbread Houses & Santa | Gattitown | 12/13, 11A-3P
Mini Yule Market | Creatures of Whim | 12/13, 12P-4P
Sip & Shop Holiday Market | Intl Book Project | 12/13, 12P-4P
Plant Lady Holiday Workshop Greeneryfest | Three Pines Herb Farm (Cynthiana) | 12/13, 12P-4P
A Wonderful Woodford Christmas | Versailles Entertainment District | 12/13, 12P-5P
Santa Station | High Bridge Fire Station (Wilmore) | 12/13, 1P-3P
Winter Wildlife Tree Decorating | Woodford Co Library/Walter Bradley Park (Midway) | 12/13, 1P-3P
Christmas Dog Photoshoot benefiting LHS | Ethereal Brewing | 12/13, 1P-4P
Pet Santa Photos | Noble View Vet (Georgetown) | 12/13, 1P-4P
Little Chef Holiday Workshop | Amy’s Asian Kitchen (Winchester) | 12/13, 1P-5P
Pet Photos with Santa | Boston Road Animal Clinic | 12/13, 2P-4P
The Holiday Market | Franzetti Bellisima | 12/13, 2P-4P
Meet Black Santa | Wiseguys II Barbershop | 12/13, 2P-4P
CBB Christmas Party | Country Boy Brewing (Georgetown) | 12/13, 2P-7P
Holiday Highlights Tour | KY Old State Capitol (Frankfort) | 12/13, 20; 3P-3:30P
Winter Balloon Glow | Wildside Winery (Versailles) | 12/13, 4P-7P
Santa Paws Photos | Louis Flower Power | 12/13, 4P-7P
Illuminated Evenings | Shaker Village (Harrodsburg) | 12/13, 20; 4P-8P
CANCELLED: Live Nativity | Lafayette Church of the Nazarene | 12/13, 5P
Festival of Living Windows | Downtown Versailles | 12/13, 5P-7P
Meet Black Santa | Well Groomed Barbershop | 12/13, 5P-7P
Santa in the Winter Village | Gatton Park | 12/13, 6P-8P
A Sadieville Christmas | Sadieville Depot | 12/13, 6P-8P
Drive Through Bethlehem | South Elkhorn Christian Church | 12/13, 6P-9P
Raqs al-Nour: A Winter Dance Affair | Arabesque World Dance | 12/13, 6P-10P
Polar Express Movie Experience | Rohs Opera House (Cynthiana) | 12/13, 7P
Sounds of Christmas: Miss Tina Fondren | The Willow | 12/13, 7:30P-9:30P
Christmas PJ Bar Crawl | Public Well, Neon Nights (Nicholasville) | 12/13, 8P
Salsa for Santa: Holiday Toy Drive Latin Dance Social | El Jefe Mexican Grill | 12/13, 9P-12A
Ugly Sweater Christmas Party | Tapster | 12/13, 10P
Christmas Tea | The Apiary | 12/13-12/14
Breakfast with Santa | Joseph-Beth Booksellers | 12/13-12/14, 9A
Holiday Open House | Street Scene Vintage | 12/13-12/14
Holiday Ho-Ho-Ho-Down | Wisebird Cider | 12/13-12/14
Christmas Market | Evan’s Orchard (Georgetown) | 12/13-12/14
Holiday Hop & Help | Downtown Georgetown | 12/13-12/14
‘The Nutcracker’ presented by Kentucky Ballet Theatre | Lexington Opera House | 12/13-14, 12/20-21
Holiday Classes | Various Locations | 12/14
1P | Holiday Cookies | The Grove
1P | Watercolor Christmas Cactus Painting | Mick’s Pot Spot
2P | Merry & Bright Rustic Snowmain | Painting with a Twist
3:30P | Yule Log Cakes | Harkness Edwards Vineyards (Winchester)Candlelight Tours | Ashland, Henry Clay Estate | 12/14
Holiday Showings: ‘Meet Me in St. Louis’ | The Kentucky Theatre | 12/14, 17-19
Scenic Train to Brunch with Santa | Kentucky Railway Museum (New Haven) | 12/14, 21; 9:45A
Breakfast with Santa | Carson’s | 12/14, 11A-2P
Meet Black Santa | Main Event | 12/14, 11A-2P
Holiday Brunch at the Distillery | Woodford Reserve (Versailles) | 12/14, 11:15A
Annual Music Bake Sale & Vendor Market | Beaumont Presbyterian Church | 12/14, 12P-2P
Christmas Pop Up Party | Christy & Co Salon | 12/14, 12P-6P
Pet Santa Photos + Adoption Event with FairyTails | Pet Supermarket | 12/14, 1P-4P
Santa’s Sangria Sunday with Trippin’ Roots | Wildside Winery (Versailles) | 12/14, 1P-4P
Art’r Barter: Holidaze $10 Art Market | Luigart Studios | 12/14, 1P-5P
Santa at Saxony | Saxony Farm | 12/14, 1:15P-3:15P
Pet Pictures with Santa | PetVet365 (Richmond Rd.) | 12/14, 2P-4P
Alltech Celebration of Song | Alltech Arena (The Kentucky Horse Park) | 12/14, 2:30P
Elf on the Shelf Tea | Lexington Tea & Brie | 12/14, 3:30P-5P
Songs of the Christmas Season by Cantabile Vocal Ensemble | David’s Fork Baptist Church | 12/14, 4:30P
Bedtime Stories with Santa | Louis Flower Power Shop | 12/14, 7P
Holiday Sunday Dinner Showcase & Fashion Show | Black & Williams Neighborhood Center | 12/13, 5P-11P
Triangle Park Ice Rink | Triangle Park | 10/25-?
Holiday Castle Tours | The Kentucky Castle | 11/5-?
Midway European Christmas Market | Downtown Midway | 11/7-12/19, Fridays, 6P-9P
Louis Christmas Shop | Louis Flower Power | 11/21-?
Visits with Santa | 11/29-12/14, Various Fridays-Sundays, 4P
Legend-ary Festival of Lights | Legends Field | 11/21-1/4
Trees of Hope Celebration | 11/21-11/23
Paws & Claus | 12/7
First Responders Night | 12/10
Ugly Christmas Sweater Night | 12/11
Santa Hat Giveaway, Teacher Appreciation Night | 12/12
Princess Night | 12/13
Christmas Tree Shop | Saxony Farm | 11/24-?
Christmas at Mustard Seed | Mustard Seed Hill (Millersburg) | 11/28-12/23
Shaker Christmas by Candlelight | Shaker Village (Harrodsburg) | 11/28-12/28, Fridays + Sundays, 5:30P-7:30P
Southern Lights | The Kentucky Horse Park | 11/28-12/31, 5:30P-10P
Holiday Art Market & Auction | LexArts | 11/29-12/19
A Kentucky Christmas | Hamburg Pavilion | 11/29-12/21, Saturdays + Sundays
Holiday Meals | Holly Hill Inn (Midway)
Holiday Lunch | 12/1-12/30, M-F, 11A-2P
Holiday Dinner | 12/3-12/27, W-Sat, 6P-9P
Holiday Brunch | 12/6-12/28, Sat-Sun, 11A-2P
Holiday Lunch the Trustees’ Table | Shaker Village (Harrodsburg) | 12/1-12/31
December Downtown Shopping Soiree | Downtown Lexington Shops | 12/4-12/18, Thursdays
Winter Village at Gatton | Gatton Park | 12/4-12/23, Nightly, 5P-10P
Tree Lighting Ceremony | 12/4, 6P
Santa Trains | Kentucky Railway Museum (New Haven) | 12/6-12/21, Saturdays + Sundays
Holiday Showings: ‘The Nightmare Before Christmas | The Kentucky Theatre | 12/14-15
‘The Nutcracker Sweets’ presented by the Lexington Ballet | EKU Center for the Arts (Richmond) | 12/15-12/25
Christmas Cookie Decorating with Santa | The KY Castle (Versailles) | 12/16
Holiday Tour Luncheon | The KY Castle (Versailles) | 12/16
Holiday Showings: ‘Gremlins’ | The Kentucky Theatre | 12/16
Be Merry & Bright Ride with Pedal Power | Country Boy Brewing | 12/16, 6P
Happy Holiday Classics Wine Class | The Grove | 12/16, 6P
Murder Mystery Dinner: The Holiday Heist | Equus Run Vineyards (Midway) | 12/17, 6:30P
Christmas in Full Bloom Holiday Floral Class | The Millyard (Millersburg) | 12/17, 6:30P
Christmas Murder Mystery Dinner | Wildside Winery (Versailles) | 12/17, 6:30P-8:30P
Holiday Showings: ‘Love Actually’ | The Kentucky Theatre | 12/17-18, 22
Holiday Showings: ‘Meet Me in St. Louis’ | The Kentucky Theatre | 12/17-19
Holiday Showings: ‘White Christmas’ | The Kentucky Theatre | 12/19, 21, 23-24
Last Minute Christmas Night Market | The Void Sake Co | 12/19, 5P-10P
Holiday Showings: ‘A Very Harold & Kumar Christmas’ | The Kentucky Theatre | 12/19, 10P
Omage: Feast of the Seven Fishes | The Apiary | 12/19-12/20
Holiday Showings: ‘Die Hard’ | The Kentucky Theatre | 12/19-20
Christmas Carol Cocktail Experience | The Manchester Reserve | 12/19-12/20
‘The Nutcracker in One Act’ presented by Bluegrass Youth Ballet | UK’s Singletary Center | 12/19-12/20
Holiday Classes | Various Locations | 12/20
10A | Holiday Reed Stars | Shaker Village
3P | Holiday Cookie Decorating | Shaker Village
’A Charlie Chaplin Christmas’ by Lexington Ballet | EKU Center | 12/20
Holiday Showings: ‘Home Alone’ | The Kentucky Theatre | 12/20, 22-23
Lexington Marker’s Market Holiday Markets | Greyline Station | 12/20, 9A-1P
Signs of Winter Craft Session | UK Arboretum | 12/20, 10A-11:30A
Children’s Tea Time with Mrs. Claus | Shaker Village (Harrodsburg) | 12/20; 11A
Cookies & Cookbooks | Honeywood | 12/20, 11A-2P
Last Call Art Market | West Sixth Brewing | 12/20, 11A-5P
Gingerbread Boyz 2 Men | Thirsty Fox | 12/20, 3P
Holiday Highlights Tour | KY Old State Capitol (Frankfort) | 12/20, 3P-3:30P
Christmas Holiday Tea | Lexington Tea & Brie | 12/20, 3:30P-5:30P
Holiday Sip & Shop | Chenault Vineyards (Richmond) | 12/20, 3:30P-5:30P
Illuminated Evenings | Shaker Village (Harrodsburg) | 12/20; 4P-8P
Black Santa Experience | Lyric Theatre | 12/20, 5P-9P
Happy Holidaze Party | Cannabuzz | 12/20, 6P
Holiday Princesses in the Winter Village | Gatton Park | 12/20, 6P-8P
The Muppet Christmas Carol + Sing-A-Long | The Kentucky Theatre | 12/20, 7P
‘The Nutcracker’ presented by Kentucky Ballet Theatre | Lexington Opera House | 12/20-21
Christmas on the Farm | Ashland Acres Inn (Cynthiana) | 12/20-12/21
Holiday Showings: ‘White Christmas’ and ‘It’s a Wonderful Life’ | The Kentucky Theatre | 12/21, 23-24
Holiday Drag Show | Old North Bar | 12/21
Scenic Train to Brunch with Santa | Kentucky Railway Museum (New Haven) | 12/21, 9:45A
Santa Party | District 7 Social | 12/21, 12P-2P
Charles Phoenix Holidayland | Lyric Theatre | 12/21, 2P
Holiday Showings: ‘Love Actually’ | The Kentucky Theatre | 12/22
The Lexington Ringers in the Winter Village | Gatton Park | 12/22, 7P-7:30P
Holiday Showings: ‘Home Alone’ | The Kentucky Theatre | 12/22-23
Holiday Classes | Various Locations | 12/23
Christmas Centerpiece | Poppy’s Flower Bar
A Very Merry Mill Yard Morning | The Mill Yard (Millersburg) | 12/23, 9
The Lexington Singers in the Winter Village | Gatton Park | 12/23, 7P-7:30P
Holiday Showings: ‘White Christmas’ and ‘It’s a Wonderful Life’ | The Kentucky Theatre | 12/23-24
BurLEX Heaux Heaux Holiday Show | Al’s Bar | 12/27, 9P
Dolly Parton’s Smoky Mountain Christmas Carol | Lexington Opera House | 12/28-12/28
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In-Person Options
Thanksgiving Brunch Buffet | Infinity Rooftop | Buffet-Style | 11A-3P
Thanksgiving Brunch Buffet | Rackhouse Tavern | Buffet-Style | 11A-3P | $60/adult, $25/child
Thanksgiving Feast | Marriott Griffin Gate | Buffet-Style | $75/adult, $27/child
Prix Fixe Thanksgiving Dining | Shaker Village (Harrodsburg) | $58/adult, $29/child
Thanksgiving Meal | 33 Staves/Origin Hotel | 11A-4P | $60/adult, $25/kid
Pre-Order/Carry Out Options
The Apiary: Full Meal Carry Out | Includes turkey, sides, rolles, and dessert | Pre-order through 11/21
Bella Notte: Full Meal Carry Out | Includes Turkey, sides, dessert | Pre-order through 11/19
City BBQ: Various Sized Meal Carry Out | Includes meat, sides, and buns
Martine’s: Full Dessert Menu
North Lime: Hand Turkey Donut Decorating Boxes | Pre-Order Through 11/24
Proud Mary BBQ: Full Meal Carry Out | Includes meats, sides, desserts | $199/family meal
Rackhouse Tavern: Turkey Takeout
Shaker Village (Harrodsburg): Full Meal Carry Out | Comes with Turkey, starters, sides, and dessert | $58/adult, $29/child
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Bricks & Minifigs: 30%, 10% off, and BOG50% deals
Designer Consignor: 20% off | Friday-Saturday
Clothes Mentor: 20% off clothes | Friday
Jeff Ruby’s: Gift card sale | Friday-Sunday
Lexington Salt Cave: 15% off retail, gift card sale
Local LEX Market: 20% off entire store | Friday-Saturday
Shaker Village: 20% all full priced merchandise | Saturday
Stephen Lawrence Ltd: 20% Everything | Friday + Saturday
General Holiday Sales + Promotions
Darling Wine Bar: Annual Thanksgiving Holiday Fire Sale | 11/22, 2P-5P
Drake’s
West Sixth: Holiday Bingo | 12/1-12/31
7 Brew: 7 Days of 7 Brew | 12/7-12/13
Christmas Dining
In-Person Options
The Granddam: Open 3P-7P
Pre-Order/Carry Out Options
City BBQ: Various Sized Meal Carry Out | Includes meat, sides, and buns
Crank & Boom: Ice Cream Pies | Pre-Order by 12/15
New Year’s
New Year’s Eve Eve with the Bolo Mules | The Burl | 12/30, 8P
NYE Prix Fixe Dinner | Honeywood | 12/31, 5P-9P
Elkhorn Tavern Bourbon Club NYE Dinner | Elkhorn Tavern | 12/31, 6:30P
New Year’s Eve Hike | Shaker Village (Harrodsburg) | 12/31, 8:30P-10P
Belle’s Cocktail House | NYE Blacktie & Bubbles | 12/31, 9P-2A
The Burl | New Year’s Eve with the Bolo Mules | 9P
Double Tree | New Year’s Eve Celebration | Includes celebration and accommodations | 21+
Greyline Station | Soul Blues NYE | 9P-1A | 21+ | Live music, champagne toast
The Grove | Midnight Inferno NYE Party | 8P-1A
The Kentucky Castle | The Black & White Ball
Lexington Legends | NYE Under the Lights | 5P-1A
The Manchester Hotel | Casino Royale NYE Spectacle | $125/person
Manchester Music Hall | Cosmic Countdown NYE Party | 8P
Mirror Twin Brewing | NYE 2026 | Drink specials, champagne toast, late night food specials
West Sixth Brewing | NYE Celebration | 7P | $100/2 person table | Includes table reservation, food, gifts, champagne, beer
Wise Bird Cider | Rhinestone Cowboy | 8P-1A | 21+ | Western-Inspired dress code, champagne toast
Holly Hill Co: NYE Take Out Dinners | $98/meal (feeds 2 people)
Shaker Village: New Year’s Eve Getaway (12/31-1/1) | $289 includes stay, night hike, + morning breakfast
Food, Drink, & Decor
Food & Drink
Andy’s Frozen Custard: Reindeer Tracks Concrete, Santa Brownie Sundae, Andy Nog
Bad Ass Coffee: Holiday flavored drinks + beans
The Bear & The Butcher: Holiday food + drink menus (alcoholic)
Biscuit Belly: Holiday themed coffees
The Burg Coffee Co (Lawrenceburg): Holiday drink specials (coffee, matcha, lotus energy)
Char: Holiday Drink Specials (coffee, hot chocolate)
Coffee Times: Holiday Coffee specials
Crank & boom: Holiday ice cream flavors (peppermint, spiced cookie, etc.)
Drinklings Coffee House (Wilmore): Holiday coffees
Hound & Horse Bakery: Holiday dog cookie boxes | Order by 11/24
Human Bean: Holiday drinks (coffee, energy, cocoa)
Leestown Coffee House: Holiday drink specials (coffee, matcha)
Lussi Brown Coffee Bar: Holiday drinks (Both NA and alcoholic)
McDonald’s: The Grinch Meal
McLeod’s Coffee House: Holiday drink specials (coffee, tea)
Mercantile Coffee & Feed (Nicholasville): Holiday themed drinks (coffee, cocoa, etc)
Mirror Twin Brewing: Holiday Cocktails (chai, cranberry, cinnamon, etc)
Old School Coffee: Holiday drink specials (coffee)
Papi’s: Boozy hot chocolate special
Parlor Doughnuts: Holiday donuts + coffees
Playa Bowls: Holiday Drinks, smoothies, bowls
The Sweet Boutique (Cynthiana): Holiday drink specials (coffee, tea, lotus)
West Sixth: Beer Advent Calendars, Barrel Aged Christmas Ale
Decor & Accessories
Ada & Lo: Christmas Decor
