A Holly Hill Holiday Menu with Bourbon Pairings

Here, Ouita and Chris Michel of Award of Excellence–winning Holly Hill Inn present a holiday menu for home cooks. Bourbon-brined pork roast is the center of this feast, with Bourbon-based cocktails and fine wines paired with each of the four courses. Most importantly, nearly all the work is done in advance, so the chef can meet and greet for a change. Enjoy!

Holly Hill’s Holiday Menu for Wine Spectator

Cocktail Hour

Cheddar Wafers and Sweet and Spicy Pecans

• Bourbon Cocktail Pairing: Honeywood Cocktail (Willett rye, grapefruit honey syrup and grapefruit juice)
• Wine Pairing: Graham Beck Brut Rosé Méthode Cap Classique Western Cape NV

Dinner Time

Roasted Kabocha Squash with Country Ham, Marcona Almonds and Bourbon Apple Cider Gastrique

• Bourbon Cocktail Pairing: Elijah Craig Old Fashioned (Elijah Craig Bourbon, spiced apple cider reduction, sassafras and sorghum bitters and apple chips)
• Wine Pairing: Leitz Riesling Spätlese Rheingau Rüdesheimer Magdalenenkreuz 2020

Bourbon-Brined Pork Roast with Tipsy Fruit Chutney and Cheese Grits Soufflé

• Bourbon Cocktail Pairing: Peytonia Punch (red wine, Buffalo Trace Bourbon, lemons, oranges, pineapple and sugar)

• Wine Pairing: Bodegas Benjamin de Rothschild and Vega Sicilia Rioja Macán Clásico 2020

Dessert

Chocolate Bread Pudding with Bourbon Butter Sauce

• Bourbon Pairing: Woodford Reserve Double Oaked
• Wine Pairing: Kopke Fine Tawny Port

Holly Hill's wafers and pecans pair perfectly with its Honeywood Bourbon cocktail. (Jessica Ebelhar)

Cocktailers

“The word cocktailers referred to the historical holy trinity of Cheddar wafers, sugared pecans and country ham biscuits. When we opened Holly Hill Inn we kept that tradition alive. In our events business, we sell thousands of each of those during Derby season especially and the holidays. The cocktailers are typically served with Bourbon. Most of the time, people would not mix the Bourbon with anything, just Bourbon and branch [water] is what they often called it.”—Ouita Michel

Cheddar Wafers

• ½ pound (2 sticks) butter, softened
• 1 pound extra sharp white Cheddar cheese, grated
• 1 egg yolk
• 2 tablespoons Dijon mustard
• 1 tablespoon brown mustard seed (optional)
• 1 tablespoon yellow mustard seed (optional)
• 1 tablespoon Coleman’s® Mustard Powder or ground mustard
• 2 teaspoons kosher salt
• ¼ to ½ teaspoon cayenne pepper, to taste
• 2 cups all-purpose flour

1. Cream the butter and cheese together in a stand mixer with the paddle attachment.

2. Once the mixture is well-combined and homogenous, add the egg yolk, Dijon mustard, mustard seeds, ground mustard, salt and cayenne pepper. Mix fully.

3. Remove the bowl from the mixer and fold the flour in by hand for a few minutes. Return to the mixer and combine thoroughly, still using the paddle attachment.

4. Chill the dough for 30 minutes, then roll into logs about the diameter of a silver dollar and approximately 10 inches long. Wrap and chill until ready to use. (The dough also freezes well.)

5. Slice thin and bake at 350° F. approximately 12 minutes. (Crisp to taste.)

Makes 2 dozen silver dollar–size wafers

Sweet and Spicy Pecans

• 1  egg white
• 1  pound pecan halves
• ⅔ cup granulated sugar
• ⅓ cup brown sugar
• 1  tablespoon salt
• ⅛ to ¼ teaspoon cayenne pepper, to taste

1. Whisk egg white until frothy; add pecans and stir to coat. Add sugar, salt and cayenne and stir.

2. Spread in a single layer on a parchment paper–lined baking sheet and bake at 275° F for 20 to 25 minutes, until crispy and lightly browned, stirring once or twice.

Bourbon Match: Honeywood Cocktail

“We named it for Honeywood Parrish Rouse and developed it when we opened our restaurant Honeywood. We wanted something that was beautiful, so it’s pink and feminine. People often think that women don’t like to drink Bourbon or rye, but that’s just not true. This is an example of a really balanced, really delicious cocktail that’s unapologetically girly, but we sell lots to men, too.”—Ouita Michel

• 1 ½ ounces Willett rye
• ½ ounce Aperol
• 1 ounce Grapefruit Syrup (see recipe below)
• 1 ounce fresh grapefruit juice
• Shake, double strain into a coupe glass; garnish with red shiso leaf
• Grapefruit Syrup
  • 1 cup shelf-stable grapefruit juice
  • 1 cup honey
  • 1 cup sugar
  • 3 slices fresh ginger

1. Combine all in a non-reactive pot. Bring to a boil, then reduce to a simmer. Simmer 15 minutes; let cool completely before removing ginger.

Wine Match: Sparkling Rosé

Graham Beck Brut Rosé Méthode Cap Classique Western Cape NV

“I always like to start a celebratory dinner with sparkling wine. And I like the rosé because it’s nice to have something with a little bit of fruit to it to go with the different flavors of the cocktails, which are a little sweet. Part of our philosophy of wine is to be reasonable and in reach but also something maybe people would be unfamiliar with. But then when you taste this and you see how good it is.”—Chris Michel

Wine Spectator Alternates: Raventós i Blanc Brut Rosé Espumoso de Nit 2022 (90, $28); Ferrari Brut Rosé Trento NV (91, $47)

Holly Hill's roasted kabocha squash pairs perfectly with either their autumn Old Fashioned or a spätlese Riesling. (Jessica Ebelhar)

Roasted Kabocha Squash with Country Ham, Marcona Almonds and Bourbon Apple Cider Gastrique

“Kabocha squash is a lot like sweet potato: It needs a lot of salt, and it’s a great foil to country ham, and the apple cider gastrique gives a nice sweet-and-sour aspect to it. The almonds are there for the crunch. Together they’re all a great pair with Bourbon.”—Ouita Michel

• One small Kabocha squash, washed thoroughly
• 2  tablespoons olive oil
• Kosher salt
• 1  cup fresh apple cider
• ½ cup toasted pumpkin seeds
• 3 ounces thinly sliced country ham (Newsom’s Prosciutto Cured Country Ham if possible)
• ¾ cup Marcona almonds, chopped
• 2  tablespoons pumpkin seed oil or other oil

1. Preheat oven to 375° F. Trim the stem off the squash, cut in half and scoop out the seeds and pulp. Cut each half into wedges, about a half-inch thick at the skin. Lay the wedges out on a sheet pan, drizzle with olive oil, and sprinkle with salt. Roast until tender and lightly brown, about 25 minutes.

2. While the squash is roasting, bring the apple cider to a boil in a saucepan and reduce by two-thirds.

3. Toast the pumpkin seeds for 5 to 10 minutes and season with salt (add a pinch of cayenne if you like a little heat).

4. To assemble the salad, arrange the wedges on a platter (or two wedges per person on individual plates). Spoon over the apple cider reduction and sprinkle with the pumpkin seeds, lightly crushing them as you go, and the almonds. Drape the wedges with country ham and drizzle with a little pumpkin seed oil.

One small squash makes 6 servings.

Prosciutto pairs best with this recipe, but any cured country ham works well in shaved-thin slices. (Jessica Ebelhar)

Bourbon Match: Elijah Craig Autumn Old Fashioned

“There’s not a party that anybody has in Kentucky where they’re not serving an Old Fashioned. Our manager at Honeywood, Leslie McPherson, developed it, and I just thought it was a really creative use of local apple cider and a way of lightening the drink slightly, and the Bourbon really shines through. It goes great with the chutney that we’re serving with the pork roast. And I love my little apple chip on the top, just for festivity.”—Ouita Michel

• 2 ounces Elijah Craig Small Batch Bourbon or Elijah Craig 12 Year Small Batch Barrel Proof Bourbon
• ¼ to ½ ounce Spiced Apple Cider Reduction (see recipe below), to taste
• 1 eye-dropper Woodford Reserve Sassafras & Sorghum Bitters
• Apple Chips (see recipe below)

1. Stir ingredients over ice then strain over a single large ice cube in an Old Fashioned glass

2. Garnish with an apple chip

Spiced Apple-Cider Reduction

• 1 cup good quality apple cider
• ½ cup brown sugar or Demerara sugar
• 1 cinnamon stick about 2 inches long
• 1 whole clove

1. Simmer all ingredients until reduced by half. Cool completely.

2. Remove cinnamon and clove before storing.

Apple Chips

• 1 good baking apple, such as a Granny Smith
• ¼ cup granulated sugar mixed with ½ teaspoon ground cinnamon

1. Peel, core, and slice the apple as thinly as possible, preferably on a mandolin.

2. Line a sheet pan with parchment paper and spread out the apple slices in a single layer.

3. Sprinkle slices with the cinnamon sugar. Bake in 225° F. oven until crispy—an hour to 90 minutes, depending upon the thickness of the apple slices.

Wine Match: Spätlese Riesling

Leitz Riesling Spätlese Rheingau Rüdesheimer Magdalenenkreuz 2020

“I love Riesling. It’s a great food wine and it doesn’t get respect from American wine drinkers. In this case, with the salty ham and starchy kabocha and salty almonds, I wanted to pick a Riesling that was just a little bit sweet. So again it’s got that sort of sweet, sour characteristic. I kind of like those long German names, because people are like, ‘What the heck is that?’ It gives people something to talk about.”—Chris Michel

Wine Spectator Alternates: Chateau Ste. Michelle-Dr. Loosen Riesling Columbia Valley Eroica 2022 (90, $20); Jorge Ordoñez & Co. Moscatel Sierras de Málaga Botani Old Vines 2023 (92, $22)

Holly Hill's Bourbon-brined pork roast isn't complete without a side of cheese grits soufflé and tipsy fruit chutney. (Jessica Ebelhar)

Bourbon-Brined Pork Roast

“My grandmother prided herself on making a delicious pork roast like this. I have found that method in Old Kentucky cookbooks. But I also found it in old Italian cookbooks and French cookbooks. It’s an old, old method, but that’s what she used to do, was she would roast pork in milk, and then the milk breaks and you strain it out and it leaves you with a delicious gravy.

It’s really nice to make a roast when you’re entertaining and it’s super easy. You can feed eight people with one roast. You don’t have to make 100 different things. The pork roast, flavorful, affordable, feeds a crowd—sounds like holiday entertaining to me.”—Ouita Michell

• 1 boneless Boston butt pork roast, about 4 pounds
• Bourbon Brine
  • 3 quarts water
  • A fifth cheap Bourbon
  • ½ cup brown sugar
  • ½ cup salt
• Braising Liquid
  • 2 cups onion, cut into medium dice
  • 1 cup celery, cut into medium dice
  • 1 cup carrots, peeled and cut into medium dice
  • 1 whole head garlic, cloves separated and peeled but left whole
  • 3 large sprigs rosemary, or 1 tablespoon dried
  • 3 large sprigs fresh sage, or 1 teaspoon dried
  • 3 to 4 bay leaves
  • 1 cup white wine
  • 2 cups chicken broth
  • 2 cups whole milk (or 4 cups whole milk if you don’t have chicken broth)
  • 2 ounces good quality Bourbon
  • 2 tablespoons butter kneaded with 2 tablespoons flour (optional)

1. Cut the Boston butt in half (it looks kind of like a square in the grocery store) into two roasts with the fat cap up, and tie each in three places.

2. Combine all the brine ingredients in a large zip-lock bag or non-reactive container. Add the pork roasts and let sit in the fridge overnight, or at least an hour or two.

3. Remove the roasts from the brine and pat dry. Season the outside with salt and pepper

4. Preheat oven to 400° F.

5. Place the onion, carrot, celery, and garlic in the bottom of a roasting pan. Lay the roasts, fat cap up, on the bed of vegetables and place in the oven.

6. Roast until the fat cap is nice and brown, about 15 minutes.

7. Reduce the heat to 350° F.

8. Add the white wine, chicken broth, milk and herbs to the roasting pan. Cover the roasting pan and place back into the oven. Note: If you can’t cover the pan, that’s fine, but you may have to add a little more milk or chicken broth during the braising process.

9. After 1 hour in the oven, remove the lid from the roasting pan and check for tenderness. Leave the lid off and roast another 45 minutes to an hour.

10. Remove the roasts from the pan and let rest on a cutting board while finishing the sauce.

11. Strain the pan juices, pressing hard on the vegetables (which can be served with the roast) and return the juices to the roasting pan. Bring the strained juices up to a simmer.

12. Add the butter and flour mixture and whisk until smooth.

13. Slice the pork roast and pour the gravy over it and the vegetables, if serving with the meat.

Tipsy Fruit Chutney

• 5 cups peeled and diced apples such as Granny Smith, Winesap, Jonathan, MacIntosh or Empire, all good, tart cooking apples
• 2 cups Tipsy Fruit (see recipe below), drained of its soaking Bourbon
• 1 orange, washed, seeded, quartered and sliced thin
• 1  onion, cut into small dice
• 1  red bell pepper, cut into small dice
• 2  cloves garlic, or to taste, minced or pressed into mix
• 2 cups brown sugar
• 1 ¾ cups apple cider vinegar
• ½ teaspoon ground cinnamon
• ¼ teaspoon ground nutmeg
• ¼ teaspoon ground ginger
• ¼ teaspoon cayenne pepper
• ⅓ cup fresh chopped ginger
• 1 ½ teaspoons salt, or to taste

1. Mix all together in a heavy-bottomed, non-reactive pot. Bring to a boil and reduce to a simmer.

2. Simmer about 30 minutes, stirring frequently until the consistency of good fruit preserves. Adjust for salt and spice.

Note: This recipe is also great substituting green tomatoes for the apples.

Tipsy Fruit

• ½ cup golden raisins
• ½ cup dark raisins
• ½ cup craisins or dried cherries
• ½ cup dried apricots cut in half
• Favorite Bourbon to cover (I  use Woodford Reserve Distiller’s Select)

1. Place all the fruit in a pint jar. Cover with Bourbon. Let soak for at least 2 days, or for 2 to 6 weeks. You can use this mix of fruit or all one kind, whatever you have.

Holly Hill Inn Cheese Grits Soufflé

• 2 cups water
• 2 cups milk
• 2 teaspoons salt, or more to taste
• 1 cup Weisenberger Mill stone-ground white grits
• 2 cups grated sharp white Cheddar cheese
• ½ teaspoon cayenne pepper
• 6 eggs, separated

1. Bring water, milk and salt to a hard boil in a heavy 2- to 4-quart pot with a lid.

2. Add grits, reduce heat and stir until the liquid comes back to a simmer and the starch begins to develop. Cover the grits and lower the heat as low as possible. (At Holly Hill, we just let the grits sit over the pilot light for about an hour and a half, “letting them swell.”) If you don’t have this kind of time, the grits should cook over very low heat for about 30 to 40 minutes. Check them occasionally to make sure they don’t scorch on the bottom, but don’t stir too frequently.

3. Remove from heat and add the cheese and cayenne. Whisk to combine the egg yolks, and stir them into the grits. Whip the egg whites until stiff and fold into the grits.

4. Turn into a buttered 6-cup soufflé dish and bake at 375° F. until golden brown and puffed on top.

Note: For an extra-rich result, substitute heavy cream for milk in the recipe. And for the love of all things Southern, please don’t use instant grits. The grits can be made a day ahead, cooled and made into a soufflé the next day. Bring them to room temperature before adding the egg yolks and beaten egg whites.

Chris and Ouita Michel share a bowl of Peytonia Punch with social media manager Tali Schroeder (far left) and general manager Donna Hecker. (Jessica Ebelhar)

Bourbon Match: Peytonia Punch

“It’s refreshing, even though the ingredients say otherwise, and most people don’t think red wine and Bourbon go well together, but they are absolutely delicious together in that punch. And it is an old recipe from the turn of the century in a cookbook written by Atholene Peyton. She was a home economics teacher out of Louisville. It was the first cookbook in Kentucky published by an African American woman. I wanted to do it for you because I wanted your readers to see that we’re mixing these two things that we think usually never should go together right in the same glass and they taste terrific.”—Ouita Michel

• 4 bottles fruity red wine
• 2 cups Buffalo Trace Bourbon
• 8 lemons
• 12 oranges
• 1 pineapple, peeled and cored
• Sugar to taste depending on ripeness of fruit, especially the pineapple; start with ½ cup
• Water as needed

1. Slice fruit and place in a large container, sprinkling each layer with sugar as you go. Pour wine and Bourbon over fruit, add water if needed to dilute slightly, and stir to combine. Can be made up to 48 hours in advance and refrigerated.

2. When ready to serve, place an ice ring in a large punch bowl and fill with punch. This will serve about three dozen guests; for a smaller crowd, simply halve the recipe. Atholene’s original recipe called for claret and the “best whiskey”!

Wine Match: Rioja or Côtes du Rhône

Bodegas Benjamin de Rothschild and Vega Sicilia Rioja Macán Clásico 2020 (90, $73)

“I wanted to go Old World, because the pork dish is old fashioned. And I didn’t want to go white wine again, because I want to do a little progression through the meal. I was thinking of something that has a little bit of earthiness to it, not super fruity, but not knock you over the head robust. This one has a neat story, because it’s the French family making wine with a venerable Rioja producer.”—Chris Michel

Wine Spectator Alternates: Bodegas LAN Rioja Gran Reserva 2017 (92, $28); Jean-Louis Chave Sélection Côtes du Rhône Mon Coeur 2022 (90, $27)

Holly Hill's chocolate bread pudding with Bourbon sauce pairs finishes off the meal on a high note with a glass of tawny Port or Vin Santo. (Jessica Ebelhar)

Chocolate Bread Pudding

“Bread pudding is so unfashionable for me, but we’ve made that recipe thousands of times. It’s one of our silver bullet recipes. The shining star for the chocolate bread pudding is the Bourbon sauce, and it goes with whatever bread pudding you make. It’s affordable, adaptable, delicious, easy to make and feeds a crowd, and those are all wonderful attributes for a holiday dessert.”—Ouita Michel

• 3 quarts cubed Italian-style bread
• 1 quart milk
• 3 eggs
• 2 cups sugar
• 2 tablespoons vanilla
• 1 teaspoon ground cinnamon
• 1 pound dark chocolate, cut into chunks
• 3 tablespoons melted butter
• Bourbon Sauce (see recipe below)

1. Soak the bread in the milk for 1 hour.

2. Mix the eggs, sugar, cinnamon and vanilla together with a whisk. Add to the bread mix. Add chocolate pieces.

3. Melt the butter in a 4-quart baking pan. Pour in the bread pudding mix. Bake at 350° F., covered, 40 to 50 minutes, then uncover and bake 10 to 15 minutes until firm and slightly crusty on the top. Serve topped with Bourbon Sauce. Makes 16 servings.

Bourbon Sauce

• 8 ounces butter
• 2  cups sugar
• 2  eggs whisked well
• ½ cup Buffalo Trace or your favorite Bourbon

1. Melt butter in a small saucepan. Add sugar and stir to dissolve.

2. Remove from heat and whisk in eggs until smooth. Whisk in Bourbon.

3. Hold in a gentle, warm water bath.

Bourbon Match: Woodford Reserve Double Oaked

“This dessert really needs a neat spirit in order to puncture through all of those luxurious flavors. Woodford Reserve Double Oaked is a great pairing because the vanilla notes in the custard really come through. It’s in a different toasted barrel twice over. That brings out a lot of that natural vanilla in the spirit itself. So I love that pairing. That’s like my old brown couch, Bourbon together. That’s something that’s tried and true.”—Ouita Michel

Wine Match: Tawny Port or Vin Santo

Kopke Fine Tawny Port

“Tawny Port has complementary flavors, and it’s not too sweet, and it’s got a little bit of acidity to it, but it’s got that sort of raisiny, spicy, nutty character with some sweetness that makes it a great complement to this dessert. It’s a little bit less 'knock you over the head' than regular Port.”—Chris Michel

Wine Spectator Alternates: Donnafugata Passito di Pantelleria Ben Ryé 2022 (94, $48/375ml); Fattoria di Felsina Vin Santo del Chianti Classico 2017 (94, $65/375ml)

Straight Up: How to Match Neat Bourbon with Food with Jack Bettridge

Granted, Kentucky hospitality is hard to beat, but the good news is that while you’re waiting to visit Bourbon country and dine at Holly Hill Inn, you can make pairings with the state’s native spirit at home. It’s a whiskey with a broad flavor palette that will strike partnerships with a range of foods you eat regularly.

Whether your plan is to match a dram with every course or make spot pairings, a few factors can point the way. Consider grain content: Being made mostly with corn, Bourbon is inherently sweet, but the other grains that make up the mash bill fine-tune it. Mix corn with rye (the usual case) and the whiskey is spicier and tart. Substitute wheat and it smooths the taste. The aging method is also paramount because Bourbon takes much of its flavor from wood casks very quickly—more than twice as fast as Scotch. Alcohol content, which runs a gamut from 80 proof to over 130 proof, can also help wend the way through a menu.

Starters

Beginning at low proof keeps the palate fresh. Basil Hayden’s, at 80 proof, still complements a salad dressing with its zesty, rye-forward grain recipe. It’s also helpful to choose youth. At about three years old, the youngster Rabbit Hole Cavehill (90 proof) is still sassy, with fruit and spice notes.

Red Meat

Bourbon and red meat make an almost can’t-go-wrong pairing because both are savory and full-bodied. But each cut deserves special consideration.

Rib eye, the big boy, needs a full-bodied liquor that won’t disappear. Extra-aged pours (12 years and up) aren’t just mellow; they have charred notes to go with the whiskey’s inherent caramel and vanilla. Consider Jefferson’s 18, Baker’s 13 and Pappy Van Winkle 15. Superhigh-proof whiskeys, such as the barrel-proof editions from Elijah Craig and E.H. Taylor, will also balance nicely.

Filet mignon, among the leanest of steak cuts, deserves not only delicate treatment but a range of flavors to complement its own. With its wheat recipe, Maker’s Mark is smooth yet complex. The No. 46 version, featuring extra aging with seared French oak staves, is toasty.

Veal, the tenderest of red meats, requires a whiskey that won’t overpower it but still offers a range of tasting notes that will set off its subtle charms. Eagle Rare 10 Year Old is more toffee than caramel, and its citrus leans to sweet orange, not lemon.

Lamb is usually described as savory and gamy, but its tanginess is what separates it from beef and makes it a candidate for pairing with Woodford Reserve, a whiskey with a high rye content and notes of cinnamon, maple, cocoa and that perennial lamb partner, mint.

Fowl

Chicken, with both white and dark meat, is hard to generalize about. With a grilled breast, it’s fun to build on the mild canvas with the contrasting flavors of charcoal and fruit that Blanton’s presents. Heavily spiced wings and fried chicken suggest entry-level but formidable Bourbons such as Jim Beam, Heaven Hill or Evan Williams Black. The same applies to other white meat and pork ribs.

Fish

It’s best not to overpower white fish with extremely full-bodied whiskey, lest you drown its charms. But complexity of flavor is a must. That’s where Michter’s Toasted Barrel Finish fits the bill. A secondary aging in toasted—not charred—barrels adds delicate notes of cinnamon, brown sugar, vanilla and, well, toast. For fattier fish, try Jack Daniel’s Bottled in Bond. Technically it’s a Tennessee whiskey, but it passes for a Bourbon and is bold, sweet and oaky, with caramel, meaty fruit and baking spices.

Dessert

Sure, they make bonbons with chocolate and whiskey, but cutting out the middleman and creating your own custom cohesion of the two renders better results. The notes of vanilla, maple candy, toffee and orange in Old Forester 100 proof come alive with chocolate.

Pairing with ice cream is an opportunity to go against type. Choose a full-bodied Bourbon at a higher proof. The cream will mellow the edges and fetch hidden flavors. Russell’s Reserve 15 Year Old, at 117.2 proof and unfiltered, has plenty of secrets to work with, especially its cherry notes.

Cheese is kind of a no-brainer. It's normally enjoyed with Sherry and Port, so try one of the Bourbons that are extra aged in casks formerly used to age those wines. Angel’s Envy Port Finished is a sultry dram of red berries, maple candy, toffee and licorice that’s an exciting contrast to cheese.