Red Herring makes three versions of the Old Fashioned. | Photo by Sara Havens

I’m pretty sure Mayor Greg Fischer has been pacing around his office the last few weeks, wringing his hands and sweating in nervous anticipation. Would the Bar Belle deliver her annual Christmas list of the best Old Fashioneds in town? Could she? Should she?

Of course she would, could and should — what else is there to give a mayor who has everything? (I’m still trying to sneak a peek at his bourbon collection, so perhaps this will score me an invite.)

But first, a little history. I used to harass the mayor every Derby while we sipped cocktails (and by we, I mean me) on the Belle of Louisville during the Great Steamboat Race. I asked him each year how I could earn a key to the city, and each year he told me I had to do something positive for the community.

Go figure.

So, I finally proved I’m an upstanding citizen because I host a pub crawl every year that encourages people to support local businesses. But that wasn’t enough. In 2015, he challenged me via Twitter to find the city’s top Old Fashioneds — the official drink of Louisville — and I quickly went to work scouring every tavern and watering hole in Jefferson County.

The Bar Belle earned a key to the city in 2015.

I delivered him a list on Sept. 18. 2015, and one month later, he handed over the key to Louisville at a ceremony at Bourbons Bistro that included bourbon, a band and lots of hand-shaking.

I thought my duties were done, until I ran into him the following year near the holidays, and he asked — no, pretty much insisted — that I keep adding to the list.

So last year for Christmas, I gave him five more. I don’t think he ever thanked me, but I could sleep at night knowing his invention of the word “bourbonism” did not go in vain.

And now, the wait is over.

The old-school cocktail believed to have been invented at Louisville’s Pendennis Club in the 1880s can be made a variety of ways, but at its core, the Old Fashioned is bourbon, bitters and sugar. Simple, yet delicious. Easy, yet complex.

1) The Village Anchor — 11507 Park Road (Anchorage) — $10

Look at that delicious Blackberry Old Fashioned! | Photo by Sara Havens

Although many visit this upscale Anchorage restaurant for the food, I stow away in the Sea Hag, the dark, mysterious basement bar where I pretend it’s 1923 and I’m a flapper trying to score an illegal cocktail. Anyway, this place has two delicious versions of the drink — the Blackberry Old Fashioned and the Brown Sugar Old Fashioned.

I brought along a friend so we could try both, and if I had to choose, I would say the Blackberry is the best. Made with Maker’s Mark, blackberry-infused simple syrup and Angostura bitters, it was fresh, original and still made bourbon the star of the show.

The other one, however, was far from being an extra — it could score an Oscar for Best Supporting Actor, hands down. Made with Old Forester Single Barrel (selected by Village Anchor), brown sugar and Angostura bitters, it was sweet and delectable with every sip. Bartender Adam said the Brown Sugar version is the bar’s best-seller, so there’s that.

Both can be had for $10 each.

2) Dish on Market — 434 W. Market St. — $12

Got a yummy Old Fashioned and my Urban Bourbon Trail stamp at Dish. | Photo by Sara Havens

Just because a drink is premade does not mean it’s weak or lesser than making it fresh. I admit, though, I was a bit worried when Bartender JBird filled up a glass with some ice and then went over to a mini barrel to pour out the restaurant’s Barrel-Aged Old Fashioned. But after one quick sip, I realized I had struck gold.

You see, they don’t batch up their Old Fashioned to get it served quicker, they do it so the bourbon can mingle with the bitters and simple syrup. And this version is made with Maker’s 46, Fee Brothers’ bitters, simple syrup and a twist of lemon peel, topped with those mouth-watering Luxardo cherries.

Again, the bourbon stole the spotlight, as it should, and this little drink packed quite a punch. It was worth every cent of the $12 cost.

3) Red Herring — 1757 Frankfort Ave. — $6-$11

Behold the Bold Fashioned from Red Herring. | Photo by Sara Havens

It shouldn’t surprise you that a bar that boasts more than 100 cocktails would have three versions of the Old Fashioned, nor should it surprise you that I ordered all three. (For the record, I did not finish them all — the friendly stranger sitting next to me helped.)

Bartender Chad Reid quickly got to work making the first one, called Bittered Sling ($6), which is made with Heaven Hill 6 Year and Angostura and orange bitters. It was simple and to the point, served over two large rocks with an orange peel.

Bartender Chad Reid knows his way around the bar. | Photo by Sara Havens

While he was hard at work, Reid explained that my cocktail of choice was the reason he first got into the industry. The intricate recipes and flavors lured him out of the kitchen to behind the bar, and he hasn’t left that spot since.

“The Old Fashioned is what got me into the business, the Manhattan is what kept me here,” he said.

Next, Reid whipped up the Red Herring ($6), the restaurant’s namesake cocktail that is made with Heaven Hill 6 Year and orange and black walnut bitters. This was one of the lightest-colored Old Fashioneds I had seen, but it tasted pretty damn good — with a slight hint of walnut.

Finally, he moved on to the mac daddy of Old Fashioneds — the Bold Fashioned ($11), created by Bartender Michael Shelley in 2012 that uses Old Forester Signature, Solerno Blood Orange Liqueur and Old Fashioned bitters.

It was my favorite of the three and had that extra zing of heat from the additional orange liqueur.

4) The Pearl — 1151 Goss Ave. — $6

The Pearl makes a simple yet delicious $6 Old Fashioned. | Courtesy of The Pearl

Old Fashioneds are always $6 at The Pearl and have been a staple since the day this Germantown bar opened. The competent bartenders make them simple and take their time stirring, crafting the perfect cocktail using Buffalo Trace, Angostura bitters and cane sugar syrup.

The night I stopped by, beverage director Susie Hoyt took my order and immediately got to work, pulling ingredients from behind the bar like she invented the drink. Although she could probably craft an Old Fashioned in her sleep by now, she gave the proper amount of time and effort to the cocktail.

For a second, I thought it was my birthday.

5) Migo — 2222 Dundee Road — $10

Migo serves its Old Fashioned in a tall glass. | Photo by Sara Havens

I’ve been hearing about the Migo Old Fashioned from a friend who frequents the little taco joint in the Highlands. I had my doubts, but I payed a visit anyway — and I’m glad I did. The Curtain’s Old Fashioned is professionally made and served in a tall glass instead of a rocks glass.


Bartender Hannah believes it keeps it colder longer. Sounds like acceptable reasoning. The cocktail contained muddled Luxardo cherries and an orange slice, and it is made with Benchmark bourbon, Aperol and Peychaud’s bitters.

Even the lady on the wall wanted a sip. | Photo by Sara Havens

My only gripe was the use of a bottom-shelf bourbon with a $10 price point, but after one sip, I got over it and enjoyed the drink as it was served. A friend of mine joined me after I had ordered, and she changed her bourbon to Angel’s Envy for a few bucks more — which also is a good idea if there’s one brand you prefer over another.

The presentation and knowledge of craft were impeccable, so instead of ordering a margarita to go with your taco, try the Old Fashioned.

* * *

So there you have it, Mr. Mayor — another year in the books, another five Old Fashioneds.

Who knew you had to work this hard to keep the key? Sheesh.