Cocktails with Kate & James: Our Favorite Bourbon Cocktails


Hello, fellow cocktail enthusiasts. James and I are amped up for the upcoming fall season. As much as we both love summer, fall in New England is magical and we’re here for all the fall flavors. Well, at least I am. I’m not sure James loves the season with as much fervor as I do. But one thing I do know he loves as much as I do is bourbon.

Let’s be real here, bourbon is a pretty versatile spirit and you can certainly drink it during any season. It goes with summer citrus just as well as it highlights spring’s seasonings, and it certainly goes extremely well with winter ice cubes. But, for this month’s Cocktails with Kate & James, we’re pairing bourbon with sweater weather and fall spice. So grab a pumpkin and a scarf, sit back, relax, and taste the flavors.

Kate’s Chef’s-Spiced Manhattan

My most beloved bourbon cocktail is simply bourbon, preferably Angel’s Envy, on the rocks. But, for the purpose of actually making a cocktail, I turned to my close second, the Chef’s-Spiced Manhattan. I learned how to make this cocktail years ago while bartending at a Boston restaurant. The chef, David Fitzgerald, who happens to be my favorite chef that I’ve ever worked with, honed this recipe over decades.

I was actually surprised he agreed to share it with me. But he’s since retired so he probably figures it’s good to carry on his legacy. To be honest, he was more of a whiskey drinker and preferred it straight up, but he knocked it out of the park with this spiced Manhattan recipe. The marinating process takes a few days, but it’s super-easy to throw together.

Infused bourbon recipe

  • 1.75 milliliters of mid-range bourbon — Chef used Jim Beam; I prefer Four Roses
  • 2 whole cinnamon sticks
  • 1 whole star anise pod
  • 13 ounces of dried sweet red cherries — I purchased mine at Trader Joe’s, but most restaurant kitchens will probably have these on hand
  • 2-3 tablespoons of good vanilla extract. Stay away from the crappy stuff. If your vanilla extract was less than $10 for a small bottle, it’s not good enough.
  • Zest of 1 orange
  • Optional: If you’re feeling fancy, and if you can get your hands on them, add a handful of cherrywood chips to add a tannin -ike quality and really bring out the woody flavors of the bourbon

If you’re making this at a restaurant, you’ll want to add all of these ingredients to an 8-12 quart clear Cambro container with a lid. If you’re making this at home, literally any plastic container with a lid will do. Store the mixture someplace warm for up to 12 hours, like on the shelf above your burners during kitchen service at your venue, or if you’re at home, place it next to your stove as you cook dinner.

From there, move it someplace cool; a walk-in will work if you’re at a restaurant or in your basement if you’re home. Leave it there for 24-48 hours. Pro tip: If you’re marinating for 48 hours, you’ll want to remove the cinnamon sticks and star anise pod after 24 hours, as the flavor can become overpowering. Once the marinating period is over, strain the bourbon into a fast pourer or any decanter you have at home.

Now it’s time to make your Chef’s Spiced Manhattan.

Chef’s Spiced Manhattan recipe

  • 2 ounces of the infused bourbon
  • 1 ounce of sweet vermouth
  • 3 dashes of bitters. I used orange bitters because I think it highlights the flavors of the bourbon best.
  • 1 Luxardo cherry to garnish. Please do not skimp on the cherry. Only Luxardo will do!

Combine the bourbon, sweet vermouth, and bitters into your cocktail shaker with ice and shake. Strain into a coupe glass and garnish with a Luxardo Cherry. Enjoy!

James’ Fall Old Fashioned 

James’ Fall Old Fashioned really embodies all of the flavors of my favorite season. It’s sweet and woody with a hint of warm spices. Definitely a great cocktail to enjoy on a chilly evening by the fire.

Fall Old Fashioned recipe

  • 2 ounces of your favorite mid-range bourbon — James used Bulleit
  • 1 teaspoon of pure maple syrup
  • 3 dashes of bitters — James used orange bitters to enhance the fall flavors.
  • 2 Luxardo cherries: 1 for the mixture and 1 to garnish. Again, only Luxardo will do.
  • Orange peel for garnish
  • Cinnamon stick for garnish
  • Pre-made spherical ice mold if you’re fancy
  • Torch if you’re even fancier

Add one Luxardo cherry to a mixing glass. Pour in your bourbon, pure maple syrup, and bitters. Muddle like you mean it. Stir, don’t shake. Place your large, round ice cube into a bourbon glass and strain the mixture over the top, and plop in another Luxardo cherry. If you’re torching, torch the cinnamon stick and orange peel. Place your garnishes in the glass. Cheers!

In case you missed it live, watch James and I make these delicious bourbon drinks on the September edition of Cocktails with Kate & James below.

Resources from this episode: