Living life between the barrel staves in Bourbon Country

Tailgating Steeplechase Style

Our annual tailgating party at the High Hope Steeplechase in Lexington has become a rite of passage for new members to our circle of friends, as well as an event those already initiated look forward to with mouth-watering anticipation.  During the early years I went through more sous chefs than Spinal Tap did drummers.  Evidently, I’m a brutal task-master in the kitchen at three in the morning which is usually when it all starts to hit the fan.  However, for the last five years we’ve kept the core of the same crew around, and along with my co-chefs (who contribute every bit as much as I do) continue to have more fun than should be allowed on a Sunday afternoon at a horse race.

It all started way back in 2000, when there were 8 of us at the party, a tabletop Coleman grill (which sat on the ground due to the lack of a table), and a menu consisting of the usual tailgate staples of burgers and brats.  A couple of people even brought chairs.  It was nothing spectacular, but we all had fun.

Three years later I decided to take this thing seriously, hauling in enough equipment to feed a Marine battalion, with the reward coming when we won “Best Food” for the first time. The following New Year’s Eve we hatched the idea to create an entire menu around bourbon. Not only would every recipe contain bourbon as an ingredient, but over the course of the menu I would use at least one bourbon from every active distillery in the state of Kentucky. The result was one of the most complicated but creatively satisfying, menu’s I’ve ever created, and a second “Best Food” award.

The Tiki Party theme in 2007 lent itself to some extreme decorating ideas. Usually the food took up so much of my attention that I never gave any thought to decorations. With a little help we decked the tent out in all manner of tiki-kitsch, and took home the “Best Theme” award. Though I was disappointed to not grab “Best Food” at the same time, it was fun to win for the decorations. Also, the television crew from TVG were impressed enough by the spread to have do a quick spot for the one of their cuts to a commercial break. When they were done filming the races, the crew ignored the well stocked hospitality tent and came back around to hang out with us.

The following year the emphasis was back on the food, and my now permanent kitchen crew and co-hosts started to take shape. This time a tequila laced menu featuring our interpretations of Cabo San Lucas and Baja California cuisine walked away with the “Best Food”. We were now feeding between 40 and 50 people each year, at that’s just the ones we knew. Countless more would wander by, especially after they announced where the best food at the steeplechase was to be found. Though I’m not overly competitive by nature, I will admit to feeling a certain amount of pride as our food is judged each year by a local chef, a graduate of the Culinary Institute of America. When the chef comes back for seconds every year, I think we have the right to brag a little.

The following year’s theme was “Mardi Gras in May”, something I’ve been wanting to do for a while. My neighbor Charlotte, breaking with tradition, agreed to a second tour of duty as co-chef and in the end turned out to be the difference maker. Even though the menu was finished earlier than ever before (see 2009 Tailgate Plans for the pre-event details), it gradually turned into the “party that almost wasn’t”. See my post of the same name for details by clicking here. In the end, we secured our fifth award in six years and won Best Food for the fourth time overall.

Preparations for the World Equestrian Games lead to the cancellation of 2010’s race, but we sprung back in 2011 with a 10th anniversary / birthday party entitled “A Pirate Looks at Forty – featuring the High Hope Pirates of the Paddock” and gathered our fifth  “Best Food” award (and our sixth award overall).  Our menu was laced with rum, and frankly so were we by the time it was all over.  I figured if I had to turn forty in a few weeks, I was going to throw a party to go with it, and why not just combine it with High Hope?
For 2012 our plans were to hang around the Caribbean for a little “Havana Daydreaming”, and focus on the food and drinks from our island neighbor 90 miles off the coast of Florida.  A few months before the event, this blog and our reputation caught the attention of the equine publication Chronicle of the Horse which included us in a feature on steeplechase tailgating (see The Chronicle Connection – March 2012 issue). Even with some Cuban inspired pork with habanero mojo, pineapple infused cocktails and Papa Hemingway’s own Bloody Mary recipe, we honestly didn’t expect to win.  But at the end of the day we had enjoyed plenty of daiquiris on were our way to a sixth “Best Food” award.  Our local paper, The Lexington Herald-Leader, gave us a nice shout out in their write-up of the day (see “Thousands Support Charities at High Hope Steeplechase”).  As you can see, the pressure and scale of this event keeps growing.

What follows below are the menu’s from our seven award winning endeavors. Each menu took around four months to plan, test and finalize. The dishes themselves are a combination of what we come up with on our own, supplemented by whatever we might find from other sources that sounds good. The goal is always to come up with as much of the menu on our own as we can, and the ones I’m most proud of are always the original creations, and some of our favorites have a way on reappearing every few years – albeit always in slightly altered forms. As this site grows and develops I’ll start posting some of the recipes from these and other events. If there is one you are just dying to have, post a comment and let me know. Enjoy!

WINNER BEST FOOD – High Hope Steeplechase “Wasting Away Again in Margaritaville” Tailgate Party (May 18th, 2003)

  • Margarita’s
  • Bloody Mary’s
  • Key Lime Rum Martini’s
  • “Backdraft” Homebrewed Red Ale
  • Salsa Borracho
  • Meatballs in Tangy Tequila Sauce
  • Hoodoo Jamaican Rum Jerked Chicken Wings
  • Bourbon and Bacon Baked Beans
  • Apple Slaw with Poppyseed Honey Dressing
  • Kentucky Chocolate Bourbon Tarts
  • Whipping Cream Pound Cake

WINNER BEST FOOD – High Hope Steeplechase “The Kentucky Bourbon Trail” Tailgate Party (May 21st, 2006)

  • Kentucky Margarita’s
  • Moon Glow’s
  • The “Build Your Own” Mint Julep Bar
  • Four Roses “Wildcat Bleu” Cheese Ball
  • Booker’s Bourbon Cheese Ball
  • Buffalo Trace Wings
  • Smoked Turkey and Swiss Finger Sandwiches with Bourbon Apple Nut Chutney
  • Kickin’ Chicken Quesadillas
  • Old Whiskey River Bayou Bourbon Shrimp Skewers
  • Old Grand Dad’s Meatballs with Peachy Bourbon Sauce
  • Jim Beam’s Bourbon and Bacon Baked Beans
  • Pappy’s Bourbon Baked Apples
  • Cornbread with Bourbon Honey Butter
  • Peachy Bread Pudding with Maker’s Mark Sauce
  • Woodford Reserve Bourbon Chocolate Cake
  • Bourbon Tarts
  • Bourbon Blossoms (Bourbon Lemon Tarts)
  • Banana’s Forrester (a Kentucky version of Banana’s Foster)

WINNER BEST THEME – High Hope Steeplechase “The Tiki Bar Is Open” Tailgate Party (May 20th, 2007)

  • Blue Tahitian Tequila Coolers
  • An original Pacific Rim inspired version of the Bloody Mary
  • Trader Vic’s original Mai Tai’s
  • Tonga ‘tini’s
  • The “Build Your Own” Rum Punch Bar
  • Kilauea Volcano Shrimp Skewers with Peanut Dipping Sauce
  • John Frum Mango Salsa
  • Warm Brie with Tropical Fruit Compote
  • Flying Tiger Wings
  • Tiki Taco’s with Haleiwa Barbecue Sauce
  • Lava Rocks (Meatballs) in a Chile Guava Barbecue Sauce
  • Hilo Tropical Fruit Salad with Papaya-Honey-Yogurt Dressing
  • Mango Lilikoi Island Slaw
  • White Chocolate Macadamia Nut Banana Pudding
  • Grilled Pineapple with Butter Rum Glaze and Vanilla Mascarpone
  • Limbo Lime Tarts
  • The Tiki’s God’s Delight – Double Chocolate Rum Cake topped with Strawberry Rum Genache

WINNER BEST FOOD – High Hope Steeplechase “Let Me Take You Down To Cabo” Tailgate Party (May 18th, 2008)

  • Waborita’s
  • Bloody Maria’s
  • Baja Typhoon’s
  • Red Rocker Seviche
  • Garden Salsa, Salsa Borracho and Mexican Beer Cheese
  • Wabo Wings with Banana-Habanero-Ginger Salsa
  • Tequila Meatballs
  • Scallops with Tequila, Tomatoes and Chiles
  • Del Mar Skirt Steak Tacos
  • Baja Beach Tacos with Tequila-Lime Salsa
  • Tropical Fruit Salad with Honey-Lime-Ginger Dressing
  • Avocado and Mango Slaw with Cuervo-Orange Vinaigrette
  • Cornbread Salad with Chipotle-Cheddar Dressing
  • Grilled Margarita Pineapple with Mint Whipped Cream
  • Margarita Tarts
  • Chocolate Kahlua’ Tarts

WINNER BEST FOOD – High Hope Steeplechase “Mardi Gras In May” Tailgate Party (May 17th, 2009)


Click here to see pictures and results of the 2009 Mardi Gras in May Tailgate Party!

  • Bayou Bloody Mary’s
  • Bourbon Street Hurricane’s
  • Bajou Margarita’s
  • Backdraft Brewery’s New Orleans Red Voodoo Ale
  • Gulf Shrimp Gazpacho Shooters
  • Bourbon Street Pecans
  • Bayou Barbecue Shrimp
  • Gator Wings
  • Creole Gumbo with White Rice
  • Cajun Crawfish Boil
  • Muffaletta Sandwiches
  • Alligator Meatballs
  • New Orleans Fruit Salad with Poppyseed Dressing
  • Creole Remoulade Slaw
  • Macque Choux
  • Banana’s Foster Bread Pudding with Rum and Bourbon Sauce

WINNER BEST FOOD – High Hope Steeplechase “A Pirate Looks at Forty” Tailgate Party (May 22nd, 2011)

Click here to view the official invitation for the 2011 Pirate Looks at Forty Tailgate Party!

  • The Maelstrom Cocktail
  • The Blind Luck Cocktail (aka “A Dead Reckoning”)
  • The Bloody Effen Mary
  • Backdraft Brewery’s Red Beard’s Red Ale
  • Backdraft Brewery’s Jolly Roger Hard Cider
  • Pork Belly Skewers with Sweet & Spicy Chile Glaze
  • Beef and Cayenne Kefta with Spicy Orange Harissa Sauce
  • Tortuga Rum Jerked Chicken Wings with Banana Ginger Habanero Salsa
  • Asian Crab Cakes with Peanut Cilantro Dipping Sauce
  • Brown Sugar and Tarragon Rubbed Lamb Skewers
  • Green Papaya and Mango Salad with Citrus Marinated Prawns
  • Spicy Indian Slaw with Chiles and Roasted Peanuts
  • Key Lime Rum Cakes with Rum Glaze
  • Chocolate Expresso Cakes with Kahlua Genache

Pirate chef and friends in front of the Jolly Roger

WINNER BEST FOOD – High Hope Steeplechase “Havana Daydreaming” Tailgate Party (May 20th, 2012)


  • Papa Hemingway’s Bloody Mary – Ernest Hemingway’s very own cocktail recipe!
  • Pineapple Sage Daiquiri’s
  • Passionfruit “Fusion” Mojito’s
  • Blood Orange Sangria
  • Backdraft Brewery’s “Communist Lager”
  • Pinchos de Camorones (shrimp skewers) with Plantain and Habanero Salsa
  • Pinchos de Pollo (chicken skewers) with Cuban Barbecue Sauce
  • Cumin seasoned Pork with Blood Orange-Habanero Mojo and Cuban Slaw
  • Sofrito Potato Salad with Spanish Chorizo
  • Ensalada Cubana with Asparagus
  • Black Beans with Garlic and Bay Leaf over White Rice
  • Tropical Ambrosia Fruit Salad
  • Banana Rum Cake with Rum Caramel Sauce
  • Pineapple Lime Tarts

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