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When you think of Winter drinks, a hot toddy or a hot buttered rum might come to mind. While these are certainly sure to warm you, and maybe even cure your sniffles, I’ve never been one for hot alcohol. I prefer rich, bold flavors served chilled. Some of my favorite winter cocktails are bourbon drinks. I find the flavor of the corn-based spirit to be a perfect compliment to seasonal fruits, like citrus, and winter spices, like clove. The complexity of many bourbons that makes them good neat also makes them good for simple, non-fussy cocktail recipes. Here are a few of my favorites.

1. Boulevardier

bourbon drinks - boulevardier

I first came across this recipe in the 3-Ingredient Cocktails book, which I would highly recommend. My husband loves spirit-forward cocktails, and this is one of the best bourbon drinks. Plus, it really is an easy cocktail to make and memorize. If you ever find yourself out at a bar, this is a great one every good bartender should know. The recipe was first published in 1927 in Harry MacElhone’s book, Barflies and Cocktails. (<–this link let’s you page through a scanned vintage copy of the book.) I used Four Roses for this recipe.


Keyword: bourbon, classic, cocktails


  • 1 oz bourbon
  • 1 oz sweet vermouth
  • 1 oz Campari
  • 1 orange twist for garnish


  • Add all liquid ingredients to a mixing glass or tin with ice.
  • Stir for 20-30 seconds until cold and properly diluted.
  • Strain into a Nick & Nora glass, express orange oil over the drink and place the peel in the drink to serve.

2. Brown Derby

Winter brings to mind all the citrus in season. I’ve always loved slicing into a fresh, ruby red grapefruit. The rich, tart flavor works perfectly with the honey in this delicious bourbon drink. The drink is named after the famous Brown Derby restaurant chain that started in Los Angeles starting in 1926. Depending on your personal preference, you can increase the grapefruit juice or reduce the amount or kind of bourbon you use. I used Wild Turkey 101. Another fun variation is to play with the honey syrup. For example, a ginger honey syrup could turn this into a completely new and delicious drink. You can read more about creating your own simple syrup variations here.

Brown Derby

Keyword: bourbon, grapefruit, honey, sour


  • 2 oz bourbon
  • 1 oz grapefruit juice
  • 0.5 oz honey simple syrup


  • Prepare honey syrup. For a cup of syrup, add a half cup of water to a half cup of honey over medium heat and stir until honey is dissolved. Cool before using.
  • Add ingredients to a cocktail shaker with ice.
  • Shake 20-30 seconds. Strain over a large ice cube in a rocks glass, or into a chilled coupe glass.

3. High Tide (riff)

When I was putting together my list of favorite bourbon cocktails, I didn’t realize how old the first two were. Not to live only in the 1920s, I bring you something brand new. I recently discovered the High Tide in a cocktail book called Tiki: Modern Tropical Cocktails by Shannon Mustipher. While the cocktail as written is fantastic, I made a few changes based on my tastes. I had been looking for some ways to use my Crude Bitters “Attawanhood #37” bitters (yum!). If you don’t have these, you can either use something close in flavor, or use a spiced simple syrup and an ounce of pineapple juice. I would highly recommend using the Reàl Pineapple Puree, but you could also use a homemade pineapple syrup. Using a banana bourbon like Howler Head is the best way to get a natural banana flavor in the drink.

Keyword: bourbon, cocktail, tiki


  • 2 oz banana bourbon (like Howler Head)
  • 0.75 oz lime juice
  • 0.5 oz allspice dram
  • 0.5 oz pineapple syrup
  • 3 droppers cherry, clove, cinnamon bitters


  • Add all ingredients to a shaker with ice.
  • Shake 20-30 seconds and strain over pebble or crushed ice.
  • Garnish however creatively you would like. Pineapple slices, freshly grated nutmeg, paper umbrellas, or plastic toys!

Best Brands to Use in Your Bourbon Drinks

I couldn’t let you go without a couple of recommendations on the best bourbons to use in your drinks. While whatever you have on hand is probably fine, if you are looking to stock your bar, here are a couple of my favorites:

  • Four Roses Bourbon – probably the best bottle of bourbon for cocktails ~$20 can buy; this is my go-to
  • Howler Head – I recently discovered this delicious banana-infused Kentucky bourbon; it’s perfect for tiki drinks that call for bourbon
  • Wild Turkey 101 – if you like a bolder bourbon, this higher rye content bourbon is aged in American White Oak barrels with the deepest char level for a big taste
  • Rieger’s Kansas City Whiskey – J. Rieger’s KC whiskey is a blend that includes their Straight Bourbon Whiskey; if you prefer your bourbon drinks a little closer to whiskey flavors, this is the choice for you!

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