Derby Day Brunch
Join us at Holly Hill Inn for a classic Derby Breakfast (aka Brunch!) in the quintessential Bluegrass setting. Enjoy a buffet filled with traditional Kentucky Derby favorites—fresh local asparagus, salad from our garden, Weisenberger cheese grits and more!
Derby Garden Party
Our annual Derby soirée is back! Join us at Holly Hill Inn for a Derby party in the garden, on the porch, in our dining room. We’re adding a fried chicken buffet this year, in addition to our Bluegrass Smorgasbord and welcome cocktail. Put on your fancy pants and fancy hats and make like the gentry up home in Midway! Enjoy lawn games, garden strolls, live music, horse racing action and more!
Derby Feast at West Sixth
Wanna party in the city? Join us and our friends at West Sixth Brewing for a downtown Derby party. Chef Agnes will be filling the buffet full of her tasty Puerto Rican and Bluegrass dishes.
Post-Derby Brunch
The Derby fun continues! Join us at Holly Hill Inn for a classic Derby Breakfast (aka Brunch!) in the quintessential Bluegrass setting. Enjoy a buffet filled with traditional Kentucky Derby favorites—fresh local asparagus, salad from our garden, Weisenberger cheese grits and more!
Tapas on the Corner Kickoff Night!
Join us for the first of many Tapas on the Corner nights!
Every Wednesday, beginning April 22, we’ll have live music, a rotating tapas menu, and wine by the glass or bottle at the corner of Clay Ave and Main St (in the Penny’s and Pomegranate courtyard)
Wine Guild Tasting
Join Steve Mancuso and the Holly Hill Wine Guild for their monthly wine tasting. The April theme is Reimagining Rioja. An optional buffet dinner precedes the tasting.
Wine Guild Tasting
Join Steve Mancuso and the Holly Hill Wine Guild for their monthly wine tasting. The April theme is Reimagining Rioja. An optional buffet dinner precedes the tasting.
Wine Me Up
Join us as we welcome Julianna Santo to host her beloved Wine Me Up at Honeywood! March is the time the Zodiac begins anew. It means a new start for all the signs, so let's reset with some wine and bites pairings curated for the Cardinal, Fixed, and Mutable signs. Come find out what the stars want you to drink.
The evening starts at 7pm with three wine and food pairings. This event is $45 per person and payment for dinner will be due at restaurant.
Kentucky Writers Hall of Fame Induction
Chef Ouita Michel’s late mother, Pamela Papka Sexton, will be honored at a special literary evening at the Kentucky Theatre, hosted by Lexington’s Carnegie Center, which she helped found. The event is free and open to the public.
Sunday Supper for Family Farms
Join the Community Farm Alliance of Kentucky and Holly Hill Inn for a casual Sunday supper celebrating Kentucky food and farmers. Holly Hill staff farmer David Wagoner will lead tours of the vegetable and flower gardens at Holly Hill Inn.
Local Mash at West Sixth
Join our BFFs at West Sixth Brewing as they celebrate their 14th birthday! Smithtown Seafood will be cooking up some tasty treats along with other chefs and restaurants from around Lexington!
Wild Game Dinner
Join Easterseals Bluegrass for its annual Wild Game Dinner, and enjoy a one-of-a-kind culinary experience as local chefs, including our Holly Hill Events team, prepare an inspired menu of wild game dishes
St. Patrick's Day
Enjoy St. Patrick’s Day specials like Corned Beef and Cabbage, Galway Seafood Chowder, and freshly-shucked oysters at Wallace Station, Windy Corner and Smithtown Seafood all day long!
Wine Guild Tasting
Join Steve Mancuso and the Holly Hill Wine Guild for their monthly wine tasting. The March theme is Sultry Southern France. An optional buffet dinner precedes the tasting.
Irish Sweet Treats at the Midway Bakery
Get lucky! Pre-order sweet Irish treats like Guinness Cupcakes, Green Velvet Cake, and Mint Cookies and Cream Pie from our Midway Bakery!
Wine Guild Tasting
Join Steve Mancuso and the Holly Hill Wine Guild for their monthly wine tasting. The March theme is Sultry Southern France. An optional buffet dinner precedes the tasting.
Shared Table: A Food Entrepreneur Summit
Join Holly Hill’s Ouita Michel and Toa Green of Crank & Boom, plus special guest Brian McCarty, at this half-day summit for food entrepreneurs who care about craft, longevity, and building something meaningful.
West Sixth Wedding Vendor Showcase
Planning a wedding? Come say hi to our Holly Hill Events team, led by Teresa and Scott Darnell, at this showcase in the West Sixth Barrel Room!
Burger Mania
Burger Mania 2026 tips off in Woodford County. Enjoy the Bluegrass Patty Melt at Wallace Station and a “Burger and Fries” at The Midway Bakery. Contest continues through March 15. Vote for your favorites and see who wins!
Ouita Michel at The Berry Center
Chef Ouita joins Mary Berry in conversation about the past and future of local food in the Agrarian Voices Lecture. Ouita will also be signing copies of her cookbook, Just a Few Miles South, which will be available for purchase at the Center.
March Wine Dinner
Join Chef Ouita Michel and Steve Mancuso of the Holly Hill Wine Guild for a three course wine dinner featuring Steve’s hand-picked wine selections.
Wine Guild Tasting
Join Steve Mancuso and the Holly Hill Wine Guild for their monthly wine tasting. The February theme is Piedmont: Not Just Barolo. An optional buffet dinner precedes the tasting.
Wine Guild Tasting
Join Steve Mancuso and the Holly Hill Wine Guild for their monthly wine tasting. The February theme is Piedmont: Not Just Barolo. An optional buffet dinner precedes the tasting.
Mardi Gras at Smithtown x West Sixth
Celebrate Mardi Gras in the taproom on February 17th with a true Fat Tuesday feast! Featuring creole favorites like gumbo, Creole greens, King Cake & more from Smithtown Chef Agnes Marrero.
Mardi Party at Windy Corner
Come on out for Big Easy specials and live music with the Honey Creek Stompers. Boudin balls, Cajun crab cakes, crawfish po-boy, chicken etouffée, beignets! Allons, laissez les bon temps rouler!
Besties Brunch
Grab your gals and girlies for a bubbly brunch. Featuring a special brunch menu from Chef Karl and fun and flirty drinks from our Bar Manager Leah!
Valentine's Dinner at Honeywood
Celebrate love with a delicious dinner from Chef Karl and toast one another with one of Leah’s handcrafted cocktails or a glass of bubbly.
Besties Brunch
Grab your gals and girlies for a bubbly brunch. Featuring a special brunch menu from Chef Karl and fun and flirty drinks from our Bar Manager Leah!
Valentine's Dinner for Two at Home
Order our delectable Valentine’s Dinner for Two at Home and celebrate love anywhere, anytime, anyway you like.
Pick up February 14th at three convenient locations
Game Day Table Reservations at West Sixth
Reserve a table for the big game in our Lexington taproom - pitcher & smithtown bites included with purchase!
🏈 Big Game. Cold Beer. Good Snacks. BAD BUNNY 🍻
Galentine's Day
Celebrate Galentine’s Day at our Holly Hill Cooking Studio. Decorate a mini red velvet cake with a friend, or your own sugar cookie heart, indulge in Midway Bakery sweets, write a love letter to future you.
Holly Hill Inn Reopening
We’ve missed you! Our new kitchen exhaust system is up and running; we passed the inspections, and we’re ready to welcome you back for dinner! For our first weekend back, we’ll celebrate with the joyous food of New Orleans and Cajun country, before we segue into aphrodisiacs just in time for Valentine’s Day.
Wine Me Up
Join Julianna Santo for this special edition of Wine Me Up: A Taste of Honeywood! Explore the Honeywood wine list with Julianna and enjoy a quartet of tasty bites from Honeywood chef Karl Lowe.
The evening begins with a welcome wine, followed by three wine and food parings. Tickets are $45 per person. Call Honeywood for reservations — (859) 469-8234!
French Provincial Dinner at Saxony Farm
Join us at beautiful Saxony Farm, just down the road from Holly Hill Inn, for an evening of comforting French classics from Burgundy and beyond.