How to Make a Benton’s Old Fashioned Cocktail: The Ultimate Guide

There is a specific moment in any bar service when the ice hits the glass and you know you are about to drink something special. For me, that moment usually involves a dark amber liquid, a twist of citrus, and a deep, satisfying aroma that hints at coffee and dark cocoa. That is the promise of the Benton’s Old Fashioned, a modern classic that reimagines the world’s most famous cocktail by adding a touch of bittersweet chocolate.

You might be wondering why this particular variation has taken over cocktail menus from Sydney to New York. It isn’t just hype. It solves a problem many people have with traditional Old Fashioneds: they can sometimes feel one-dimensional or overly harsh if the spirit isn’t perfect. By introducing a small amount of chocolate syrup, you bridge the gap between the sharp bite of bourbon and the sweet, aromatic notes of bitters. The result is a smoother, more complex drink that feels luxurious without being cloying.

The Story Behind the Chocolate Twist

To understand why this drink works, you need to look at its origin. The Benton’s Old Fashioned was created by Benjamin Franklin, the bartender behind the legendary Benton’s Bar in Portland, Oregon. He didn’t set out to reinvent the wheel; he wanted to enhance it. Benjamin noticed that many guests found the traditional Old Fashioned-just sugar, bitters, and whiskey-a bit too austere for their taste.

He experimented with various flavorings and landed on Hershey’s Special Dark syrup. Why Hershey’s? Because it is widely available, affordable, and has a distinctively bitter profile compared to standard chocolate syrups. This choice was crucial. If you use a sweet vanilla-chocolate syrup, you will drown out the whiskey. You want the chocolate to act as an accent, not the main character. This subtle addition transforms the drink into what some call a "bourbon and chocolate" experience, making it accessible to those who find straight spirits intimidating while still respecting the integrity of the original recipe.

Ingredients: Quality Matters More Than Quantity

Making a great Benton’s Old Fashioned at home requires attention to detail, but you don’t need expensive tools. You do, however, need the right ingredients. Here is what you need to gather before you start:

• Bourbon Whiskey: Use a high-quality bourbon with notes of vanilla, caramel, or oak. Brands like Woodford Reserve, Bulleit, or Maker’s Mark work well. Avoid cheap, harsh bourbons because the cold temperature won’t mask poor quality.
• Hershey’s Special Dark Syrup: This is non-negotiable for authenticity. Do not substitute with generic chocolate syrup unless it is specifically labeled as bittersweet or dark. A teaspoon is all you need.
• Angostura Bitters: These provide the spicy, herbal backbone of the drink. They balance the sweetness of the chocolate and the richness of the bourbon.
• Orange Peel: Fresh orange zest adds essential oils that lift the heavy flavors. Save the peel after juicing an orange or buy fresh oranges specifically for garnish.
• Luxardo Maraschino Cherry: Skip the bright red, sugary cherries from the jar. Luxardo cherries are preserved in marasca cherry juice and offer a tart, sophisticated finish.
• Large Ice Cube: Clear, dense ice melts slower, preventing your drink from watering down too quickly.

Step-by-Step Instructions for the Perfect Pour

Now that you have your ingredients, let’s get to the mixing process. The technique here is simple but precise. We are building the drink directly in the serving glass, which allows you to control the dilution and ensure every element is integrated properly.

1. Prepare the Glass: Take a heavy-bottomed rocks glass (also known as an Old Fashioned glass). Place one large ice cube inside. If you don’t have a large cube, two standard cubes will do, but avoid crushed ice-it will melt too fast and ruin the texture.
2. Add the Sweetener: Pour one teaspoon of Hershey’s Special Dark syrup into the bottom of the glass. Let it sit for a moment so it coats the sides slightly.
3. Add the Bitters: Add three dashes of Angostura bitters. Watch how the bitters interact with the syrup; you should see a slight separation before stirring.
4. Pour the Spirit: Add two ounces (60ml) of your chosen bourbon. Don’t measure this with a cup; use a jigger for accuracy. Too much whiskey overwhelms the chocolate; too little makes it taste like dessert.
5. Stir, Don’t Shake: This is critical. Take a long-handled spoon and stir the mixture gently for about 20-30 seconds. You are chilling the drink and diluting it just enough to open up the flavors. Shaking would aerate the drink and make it cloudy, which is not what we want for a spirit-forward cocktail.
6. Garnish with Purpose: Take your orange peel. Hold it over the glass with the pith (white part) facing down. Twist it sharply to express the oils onto the surface of the drink. Rub the peel around the rim of the glass to spread the aroma, then drop it into the drink.
7. Finish with a Cherry: Add one Luxardo cherry. Now, take a sip. Notice how the orange oil hits your nose first, followed by the warm bourbon, and finally, the lingering hint of dark chocolate.

Why This Combination Works: Flavor Science

You might be curious about the chemistry here. Why does chocolate go with bourbon? It comes down to complementary flavor compounds. Bourbon is aged in charred oak barrels, which imparts notes of vanillin, caramel, and toasted wood. Dark chocolate shares these same flavor profiles due to the roasting process of cocoa beans. When you combine them, you aren’t creating a clash; you are amplifying existing notes.

The Angostura bitters play a vital role in balancing this richness. Without them, the drink could become too sweet and heavy. The spices in the bitters-cinnamon, clove, and gentian root-cut through the fat of the chocolate and the alcohol burn of the whiskey, creating a clean finish. This balance is what separates a good Benton’s Old Fashioned from a mediocre one. It is not just about adding chocolate; it is about using chocolate to enhance the whiskey, not hide it.

Troubleshooting Common Mistakes

Even experienced bartenders make mistakes when crafting this drink. Here are a few pitfalls to avoid:

• Using the Wrong Chocolate Syrup: If your drink tastes like a milkshake, you used the wrong syrup. Stick to Hershey’s Special Dark or another bittersweet variety. Sweet chocolate syrup will overpower the bourbon.
• Over-Dilution: Stirring for too long or using small, weak ice cubes will water down the drink. Aim for a slow, gentle stir and use large, clear ice blocks.
• Skipping the Orange Oil: Many people just drop the peel in without expressing the oils. This misses half the point of the garnish. The aromatic oils are what lift the heavy flavors and make the drink smell as good as it tastes.
• Cheap Whiskey: While the chocolate helps mask some imperfections, it cannot fix bad whiskey. Invest in a decent bottle of bourbon. Your palate will thank you.

Variations to Explore

Once you master the classic Benton’s Old Fashioned, you can experiment with variations. One popular tweak is swapping bourbon for rye whiskey. Rye has a spicier, drier profile that pairs interestingly with the dark chocolate, creating a more robust drink. Another option is using a different type of bitters. Orange bitters can complement the orange peel garnish, while black walnut bitters add a nutty depth that enhances the chocolate notes.

Some bartenders also add a splash of soda water to create a "Benton’s Highball," which lightens the drink for warmer weather. However, purists argue that this dilutes the experience too much. Stick to the stirred version first, and only experiment once you understand the core balance of flavors.

Serving Suggestions

This cocktail is best enjoyed slowly, ideally after dinner or during a quiet evening. Pair it with dark chocolate desserts, aged cheeses, or even a plate of charcuterie. The rich flavors of the drink stand up well to savory foods, making it a versatile option for entertaining. Serve it in a heavy glass to keep it cold longer, and always offer a fresh batch of ice if your guests plan to linger.