Allow me to begin with a quote. Robert Simonson, a writer for the New York Times, states in his book (which is based solely on this classic cocktail), “Once an austere, perfectly balanced assemblage of whiskey, bitters, sugar and water — a cocktail in its most elemental — it had taken on several decades worth of baggage.” This couldn’t be truer of this particular cocktail. I can’t tell you how many times I’ve been served an Old Fashioned that’s been muddled beyond oblivion. And don’t even get me started on using maraschino cherries — not only do they not belong in an Old Fashioned, those neon red balls of blasphemy should be banned from the face of the earth. From the type of whiskey, to the type of sugar, to ice or not to ice, fruit or not to fruit, there’s a number of ways this cocktail can be made. While many may not be true to the original, I still enjoy exploring others’ interpretations of the drink.

In part one, Merry described her take on four different variations around town: Seven Saints, Barrelhouse 34, V. Picasso, and Quality. In part two I explore five more: Miga, Big Grove, Bentley’s, Black Dog, and Hamilton Walker’s. For someone who isn’t a fan of whiskey, Merry did a fair bit of branching out for the article. I love whiskey, but I bar hopped around town for my own article with a group of ladies who all had very different tastes in alcohol. I was excited to hear everyone’s opinion on this classic cocktail.

But first, let’s quickly break down the essentials:

1. The glass: Heavy bottomed old-fashioned glass. C’mon, its name is because of this drink!

2. Quality whiskey: It can be made with bourbon or rye, but as this cocktail is basically 80% whiskey, why choose anything sub-par? Go for the good stuff. For the whiskey-leery individual, you’re better off choosing a bourbon as it’s sweeter/smoother than its rye counterpart.

3. Sugar: The tradition of using a sugar cube is one that can easily be skipped. Go for the simple syrup instead; it’s less work.

4. Bitters (Angostura): An essential ingredient, but be careful, a little goes a long way.

5. Ice: Optional, but most prefer it. There’s a fine line between a diluted, watery mess of a drink and having just enough to take the edge off that alcohol burn. I think it helps bring out the flavors as well.

6. Fruit/garnish: If there were any part of this cocktail that could cause a divide among friends and strangers alike, it’s this one. I don’t want muddled pulp in my cocktail, and get out of here with those abominable maraschino “cherries,” but I do feel fancy AF with a Luxardo cherry and orange peel, thank you very much.

First up, Black Dog Smoke & Ale House in Champaign. Oscar’s Old Fashioned ($6) is usually served with Medley Brothers Bourbon, but sometimes they change it up. On this particular night it was made with Evan Williams and they infuse their bourbon of choice with cherries and oranges. They also use a brown sugar simple syrup and bitters, which makes complete sense for a BBQ establishment. I wouldn’t come here just for the drinks, but if this were served alongside a rack of ribs I’d be okay with it. We dubbed this an “Old Fashioned For The Masses.” It was very sweet, there was a lot of orange, and it tasted fairly watered down — I don’t think it was just the ice cubes. The sweetness overload from infused bourbon along with the brown sugar simple syrup took the whiskey-as-the-star out of the drink. Out of the five we tried, this was the favorite of our non-bourbon loving friend. There was also a weird mushy cherry at the bottom that did not taste all that great — we all know how I feel about that by now. 

Next on our list was Miga. The atmosphere here goes a long way in enjoying fancy cocktails. We sidled up to the bar and watched the chefs make sushi as we waited for our drinks. A few of the girls ordered other cocktails from the menu (The Thyme Is Now is so good!), but were still willing to partake in my whiskey adventure. The Miga Old Fashioned ($12) is made with Akashi whisky (yep, follows the Scottish spelling), a Japanese whisky that’s got a smoky flavor to it like a scotch. It was strong, but drinkable and smooth. Presentation was great — very sophisticated — as it was served in a nice, heavy rocks glass with a large sphere of ice and a Luxardo cherry. A slice of orange also accompanied the drink, but it didn’t bother me too much; it was intact and fresh (not a muddled mess). The bartender was also attentive and knowledgeable. It was interesting that the longer you took to sip the drink, the flavor profile changed slightly as the large sphere of ice slowly melted. Because of the type of whisky used, this cocktail isn’t all that approachable to an Old Fashioned newb. For me, it was an enjoyable change of pace and the smokiness was intriguing. I loved it. We called this one the “High Roller.” 

Third on our list was Big Grove Tavern. The Big Grove Fashion ($10) uses Buffalo Trace bourbon, which is pretty standard and a good choice. I really liked the presentation for this one — a skewer through an orange peel (which I’m sure they first lit with a match and rubbed around the rim of the glass) and a Luxardo cherry. If you’re looking for the quintessential Old Fashioned — hitting all the right notes in terms of appeal, sweetness, quality of whiskey, garnish, etc. — get the Big Grove Fashion. Because this one was on the sweeter side, our friend the whiskey newb liked this version better as well. Having tried this one right after Miga, it certainly felt like we were getting more drink out of it because the glass wasn’t full with a giant ball of ice. We dubbed it the “The Ol’ Familiar.” 

Bentley’s Pub was up next. I generally like their cocktail creations and they’re always cheaper than most, but man did this Old Fashioned ($6) miss the mark. I believe they also infuse their bourbon (typically Buffalo Trace or Benchmark) with tart cherry and use a brown sugar simple syrup. There wasn’t enough bourbon flavor, and it was extremely watered down (I think they did the big no-no of muddling and shaking?) and… there was a maraschino cherry to top it all off. 

Our last stop was Hamilton Walker’s. The bartender first asked me if I wanted bourbon or rye. I chose rye as I like mine a little less sweet. It was a very strong Old Fashioned ($9) in terms of alcohol versus syrup/bitters. The whiskey was certainly the shining star here as it was made very simply and without the addition of a lot of simple syrup or fruit. Even though the glass was filled with ice cubes it didn’t taste watered down. It was definitely a sipper. An orange peel and Luxardo cherry accompanied the drink as garnishes. While I don’t often go to Hamilton Walker’s for the food, we’re always hanging out there for cocktails. The bartenders are extremely knowledgeable and the cocktail menu is full of old classics. While it was still much too strong for others in our group, my whiskey loving friend and I rated this one and Miga's at the top of our list. Because we wanted to take our time with this one — to savor it, sip on it — we called it “The Conversationalist.” 

One cocktail, five different bars, five very different interpretations. While it’s true that some of these did indeed take on some "extra baggage," it really is all about personal preference. Where do you go for your favorite Old Fashioned?

Read part one in this series. 

Photos by Bobbie Bonebrake