Starters
- Maryland Style Crab CakeLump Crab, Smoked Remoulade, Roasted Corn Fennel Slaw$24.00
- Deviled EggsLobster, Chives, Salmon Roe$12.00
- Whipped Goat Cheese FondueSpiced Chickpea, Roasted Tomato, Crostini, Herbs, Arbequina Olive Oil$14.00
- Rock Shrimp & Calamari Fritto MistoOld Bay, Peppadew, Pepperoncini, Meyer Lemon Aioli$20.00
- "Millionaire" Braised Benton's BaconPickled Cucumber Salad, Benne Seed$16.00
- Horseshoe Onion RingsComeback Sauce, Herbs$12.00
- Pimento Cheese, Sweet Corn & Bacon AranciniRoasted Red Pepper Coulis, Parmesan Cheese$14.00
Charcuterie + Cheese
- Pony BoardSelection of 3 Meats & 3 Cheeses$32.00
Raw + Chilled
- Oysters On The Half Shell$20.00
- Matt Winn's Classic Shrimp CocktailMiami Mustard, Zesty Horseradish Sauce$20.00
- King Crab Legs
- Maine Lobster Tail
- Winner's Circle Grand PlateauChef's Selection of Items From The Raw, Chilled Bar$145.00
Soups + Salads
- French Onion SoupSherry, Brioche Bread, Kenny's Kentucky Cheese$12.00
- Seafood GumboFresh Seafood, Okra, Saffron Rice$12.00
- Classic Caesar SaladRomaine Lettuce, White Anchovy, Parmigiano Reggiano, Rustic Crouton$13.00
- Matt Winn's Wedge SaladHeirloom Tomato, Applewood Bacon, Pickled Onion, Egg, Smoked Bleu Cheese Dressing$13.00
- Bibb & Kale SaladShaved Pickled Beet, Apple, Goat Cheese, Spiced Pecan, Grain Mustard Vinaigrette$13.00
Add Protein
- Butcher Cut Steak$30.00
- Chicken Breast$10.00
- Shrimp Scampi$12.00
- Salmon$20.00
Prime Steaks
- Petite Filet Of Beef$54.00
- Filet Of Beef$64.00
- NY Strip Steak$68.00
- Bone-In Ribeye$80.00
- Porterhouse$115.00
Charred Choices
- Wagyu Short RibWild Mushroom & Black Truffle Risotto, Red Wine & Bone Marrow Demi-Glace$40.00
- Steak Frites10oz Butcher's Cut with Pommes Frites & Garlic Butter$38.00
Sauces
- Bearnaise$6.00
- Red Wine & Bone Marrow Demi-Glace$8.00
- Horseradish Mustard Cream$6.00
- Chimichurri$6.00
- Brandy Peppercorn Sauce$8.00
Enhancements
- Oscar StyleJumbo Lump Crab, Béarnaise$20.00
- Scampi StyleWhite Wine, Garlic Herb Butter, Lemon$12.00
- Seared Sea Scallops$15.00
- Braised Benton's Bacon$8.00
- Bleu Cheese Crust$8.00
From the Kitchen
- Double Cut Pork ChopBourbon Brined, Spiced Apple Chutney, Sweet Potato Purée$38.00
- Pan Roasted ChickenWhipped Potatoes, Kale, Herb Poulet Demi$32.00
- Seared Sea ScallopsButternut Squash Purée, Pomegranate Molasses$38.00
- Scottish SalmonBrussel Spout, Celery Root Purée, Mint Salsa Verde$42.00
- Ruby Red TroutYukon Gold Potato & Pork Belly Hash, Smoked Almond Butter$34.00
Classic
- Macaroni & CheeseKenny's Kentucky Cheddar, Fontina, Cavatappi Pasta$15.00
- Whipped Potatoes$10.00
- Glazed CarrotsMaple & Local Honey$10.00
- Pommes FritesRoasted Garlic Aioli$10.00
- Salt Crusted Baked PotatoButter, Sour Cream. Loaded: Scallions, Kenny's Kentucky Cheddar, Bacon$8.00
Market
- Roasted AsparagusMeyer Lemon Hollandaise$14.00
- BroccoliniSea Salt, Lemon$12.00
- Sweet Potato PuréeBourbon Brown Butter, Kale, Candied Pecan$12.00
- Brussels SproutsCrisp Country Ham, Aged Sherry Vinegar$12.00
- Pan Roasted Cremini Mushrooms$14.00
Coffee
- Signature Blend$3.00
- Espresso$3.50
- Double Espresso$5.50
- Cappuccino$5.50
Seasonal Cocktails
- Peerless Post PositionShowcasing Matt Winn's Steakhouse Peerless Barrel Pick, this cocktail incorporates honey syrup, Lemon juice and housemade Peach & Apricot Tea$15.00
- The Witching HourOur seasonal variant on the tried and true margarita using Herradura Blanco Tequila, Cointreau, Guajillo Pepper syrup, muddled serrano peppers and a Tajin rim$15.00
- Cherry Blossom Gin FlipA spring makeover for the traditional gin flip using Bombay Gin, St. Germain Elderflower Liqueur, our housemade cherry & rosemary syrup, with fresh egg white$15.00
- Watermelon Basil CrushA refreshing cocktail over crushed ice using Finlandia Vodka, fresh pressed watermelon & lime juices and muddled basil$15.00
- Citrus SparklerThis springtime option will not disappoint our Sangria lovers. Grand Marnier, Sauvginon Blanc, white cranberry & lime juice perfectly compliment this cocktail with a sparkling Prosecco finish$15.00
- Raspberry & Thyme Sour MocktailAn alcohol-free sour with our housemade Thyme & Raspberry syrup combined with Yuzu and soda$11.00
Signature Cocktails
- Matt Winn's Signature Mint JulepMade with Matt Winn's Bourbon Selection using the finest Kentucky Colonel mint gently steeped in simple syrup and finished with a bitters spritz. A time-honored tradition$15.00
- The Charred StaveBarrel aged Manhattan made with Woodford Reserve Rye, Carpano Antica Formula Sweet Vermouth and two styles of bitters served in a torched Cherry Wood smoked glass$15.00
- 1876 Improved Whiskey CocktailIntroduced by Jerry Thomas in the year after Oliver Lewis rode Aristides to win the very first Kentucky Derby, we present this cocktail with subtle twists. Made with Matt Winn's Woodford Reserve Select, two bitters, gum syrup, maraschino liqueur, absinthe rinse and a lemon twist$15.00
- Smoked Maple Old FashionedTake your Old Fashioned experience to the next level with Old Forester 100 Bourbon, maple syrup, and chocolate bitters served in a smoked highball with orange peel and cinnamon stick$15.00
- The Oaks LilyDeveloped by Tim Laird in honor of the "Lilies for Fillies" Kentucky Oaks race, this cocktail is now a signature drink of Churchill Downs$15.00
- 75 DaysHonoring Matt Winn's 75 Kentucky Derbys and the average 75 days annually of thoroughbred racing at Churchill Downs. A French 75 fused with an enhanced Daisy made with Starlight Distillery Simon's 1794 gin, house made sour mix, fresh egg white and sparkling wine. Also available with vodka$15.00
Closing Cocktails
- Chocolate Nuts & BerriesChambord, Frangelico, and heavy cream shaken over ice with dark chocolate shavings to close your Matt Winn's experience$15.00
- Kentucky CoffeeMatt Winn's Signature Coffee, with Bourbon Cream Liqueur and served piping hot$14.00
- Our Colonel's FinishOur Matt Winn's Signature Bourbon presented slightly chilled and sweetened with an accent of Amaretto. Garnished with candied ginger bourbon ball$15.00
- Kentucky Caramel MochaMatt Winn's Signature Coffee, Double Chocolate Bourbon, Salted Caramel Cream Liqueur, Whipped Cream$14.00
Dessert Wines
- Dessert WinesPlease See Our Wine Book For A Selection Of Ports, Madeiras, Sherry & Sweet Wines
Rare Spirits
- Atherton 1944 Prohibition Era WhiskeySold as medicinal whisky during Prohibition$525.00
- Heaven Hill 27 YearFewer than 3,000 bottles made$525.00
- Old Heaven Hill 21 YearExport bottling with dripping red wax$850.00
- Johnny Drum 12 Year 86 Proof 1980s$250.00
- Old Grand-Dad Bottled-In-Bond 4 Year 1962$250.00
- Old Grand-Dad Portugal Export 1988$250.00
- Old Stagg 1961$265.00
- Pappy Van Winkle 20 Year$300.00
- Pappy Van Winkle 23 Year$550.00
- Very Olde St. Nick Lost Barrel 17 YearProduced in early 1980s, it was removed from crumbling barrels in the late 90s and held in hibernation until the perfect time for bottling$265.00
- Woodford Reserve, Baccarat EditionFinished in XO Cognac Barrels and presented in a Baccarat Decanter$400.00
- Dumbarton 1977The Last Drop Distillers. Single Grain Scotch Whiskey. Only 150 bottles produced world wide$1,000.00
- The Glenfiddich 2626 Year Old Single Malt Scotch$125.00
- 1925 Hors D'Age Grand Champange CognacThe Last Drop Distillers. Almost a century old. Less than 200 bottles produced$1,200.00
- Louis XIIIby Remy Martin Cognac$750.00
Flights
- Pappy Van Winkle FamilyIncludes the entire line of 10 Year, 12 Year, 15 Year, 20 Year, & 23 Year$725.00
- Heaven HillTwo pour flight consisting of The 21 Year & 27 Year$700.00
- Buffalo Trace Antique CollectionEagle Rare 17 Year, George T. Stagg, Sazerac 18 Year, Thomas H. Handy, & William Larue Weller$525.00
- Corti Brother's Van Winkle Special Reserve0.5oz Pour of Each Expression. The First Special Selection Barrels Of Julian Van Winkle & Darrell Corti. The Barrels From The Late 60's & Early 70's. Includes Red Wax, Red Wax 19 Year, Black Wax 19 Year, & Gold Wax 20 Year. These Are Considered The Rarest Bourbons In The World$8,300.00
Starters
- Kung Pao CalamariSorghum Chile Crisp, Peanut, Celery, Lime
- French Onion SoupCopper & Kings Brandy, Kenny's Kentucky Rose, Duck Fat Crouton
- Matt Winn's Wedge SaladSmoked Blue Cheese Dressing, Preserved Tomato, Candied Broadbent Bacon, Pickled Onion, Sieved Egg
Entrées
- Black Hawk Farm BurgerBroadbent Bacon, Kenny's Cheddar, Pop's Pickles, Pomme Frites, Roasted Shallot Aioli
- Steak Frites10oz Flat Iron with Pommes Frites & Garlic Butter
- Colonel Boujie Fried Chicken SandwichSweet & Spicy Glazed Fried Chicken Breast, Broadbent Bacon, Pimento Cheese, Comeback Sauce, Pop's Pickles, Truffle Pomme Frites, 24k Gold Leaf Half Bottle Veuve Cliquot
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