There are plenty of signs that harvest is approaching at Sweet Cheeks Winery: grapes beginning to ripen, the vineyard shifting toward late summer, and the anticipation of another vintage just around the corner. For our team, there’s another tradition that has marked the season over the years – a little friendly competition.

Our staff chili cook-off began as a way to gather in August, celebrate the end of a busy summer, and kick off the excitement of harvest. It was a favorite event of our founder, Dan—and he also had a reputation for being the one to beat.

After taking a break from the tradition, we brought the chili cook-off back last year. In honor of its return, we’re sharing two recipes with a little Sweet Cheeks history behind them: Dan’s famously hearty “Chilly” and our latest winning recipe, inspired by the appropriately named “World’s Second Best Chili.”

Because when Dan’s recipe is in the mix, second best might just be the highest title available.

Founder Dan’s “Chilly”

It wouldn’t be a Sweet Cheeks chili cook-off without starting with Dan.

His “Chilly” is not a subtle bowl of chili. Venison, beef, and pork create a hearty base, while jalapeño, tomato, garlic, pilsner, and a generous splash of Kentucky bourbon build layers of flavor as everything slowly simmers together.

Ingredients

  • ¼ cup butter
  • 1 lb. ground venison
  • 1 lb. beef stew meat, cubed
  • 1 lb. pork stew meat, cubed
  • 1 large onion, chopped
  • 1 fresh jalapeño pepper, seeded and minced
  • 3 tablespoons chili powder
  • 1½ teaspoons ground cumin
  • ½ teaspoon cayenne pepper
  • 2 (14 oz.) cans stewed tomatoes, with juice
  • 1 (15 oz.) can tomato sauce
  • 6 cloves garlic, minced
  • 4 beef bouillon cubes, crumbled
  • 2 (12 oz.) cans pilsner-style beer
  • 2 cups water
  • ¼ cup Kentucky bourbon

Make It

Melt the butter in a large, heavy-bottomed pot over medium heat. Add the venison, beef, and pork and cook until the meat is completely browned.

Add the onion and jalapeño and continue cooking until softened. Stir in the chili powder, cumin, and cayenne.

Add the stewed tomatoes and their juices, tomato sauce, garlic, beef bouillon, pilsner, water, and bourbon. Stir well and bring everything to a boil.

Reduce the heat to low, cover, and simmer for at least 1–2 hours, stirring occasionally, until the meat is tender and the flavors have had plenty of time to come together.

Pour It With

Make it a true Dan pairing by enjoying this recipe with a glass of his favorite red wine, Syrah!

Katie’s 2nd Best Chili

Last year’s winning chili started with a recipe Katie discovered years ago called World’s Second Best Chili. Her version takes that recipe in a slightly different direction by roasting the fresh tomatoes, chile peppers, and poblanos before they ever reach the pot. 

Roasting concentrates the tomatoes while giving the peppers a smoky, charred quality. Then everything gets a long, slow simmer, resulting in the kind of rich chili that seems made for a cool harvest evening. 

And around here, calling it the 2nd Best Chili feels particularly appropriate.

Serves approximately 8

Ingredients

Roasted Vegetables

  • 2 lbs. Roma or plum tomatoes, halved
  • 2 poblano peppers
  • 2 chile peppers, such as jalapeño or Anaheim
  • 1 tablespoon olive oil
  • Salt and pepper

For the Chili

  • 2 lbs. ground beef
  • 2 medium red onions, chopped
  • 4 garlic cloves, minced
  • 30 oz. canned chili beans, with liquid
  • 15 oz. tomato sauce
  • 6 oz. tomato paste
  • 1 tablespoon Worcestershire sauce
  • 3 cups unsalted beef stock
  • ¼ cup all-purpose flour
  • 1 tablespoon brown sugar

Season With

  • 1½ tablespoons kosher salt
  • 1½ tablespoons ground cumin
  • 2 teaspoons dried oregano
  • 2 teaspoons ancho chile powder or chili powder
  • 1½ teaspoons onion powder
  • 1½ teaspoons smoked paprika
  • 1 teaspoon cayenne pepper
  • 1 teaspoon garlic powder
  • ½ teaspoon freshly ground black pepper

Make It

Preheat the oven to 425°F. Arrange the tomatoes cut-side up on a sheet pan with the whole poblanos and chile peppers. Drizzle the tomatoes with olive oil and season lightly with salt and pepper.

Roast for 25–35 minutes, turning the peppers occasionally, until the tomatoes are softened and caramelized and the peppers are blistered. Transfer the peppers to a covered bowl for about 10 minutes, then remove the loose skins, stems, and seeds. Roughly chop the peppers and tomatoes, reserving the tomato juices.

In a large Dutch oven over medium heat, brown the ground beef with the onions. Once the beef is nearly cooked through, add the garlic and seasonings and cook for another 1–2 minutes.

Sprinkle the flour over the mixture and stir to combine. Add the roasted tomatoes and peppers, chili beans, tomato sauce, tomato paste, Worcestershire sauce, beef stock, and brown sugar.

Bring to a gentle simmer, reduce the heat to low, and cook uncovered for approximately 2½–3 hours, stirring occasionally. If the chili becomes too thick, add a splash of beef stock until it reaches your preferred consistency.

Season to taste and serve with your favorite chili toppings.

Pour It With

Malbec is a natural match. Its dark fruit and fuller body have enough character for the beef and long-simmered tomato, while the roasted peppers and smoky spices bring out the wine’s savory side.

A Tradition Worth Bringing Back

Harvest is one of the most exciting times of year at Sweet Cheeks, but it’s also one of our busiest. The chili cook-off gives our team a chance to gather before the pace really picks up – to share a meal, enjoy some friendly competition, and celebrate the vintage ahead.

Bringing it back also means carrying forward one of Dan’s favorite traditions. And while there may be a new winner each year, his “Chilly” will always hold a special place in Sweet Cheeks history.

So we’re raising a bowl, and a glass, to busy summers, new harvests, old traditions, and the pursuit of the second-best chili.

Tried one of these recipes? We’d love to see your bowl! Share your chili on social and tag Sweet Cheeks Winery so we can cheer you on.