The Speakeasy Trail

NICE 1The bar is downstairs and beneath a stairwell. Chris and I get a rush of excitement – our first speakeasy on the speakeasy trail. I knock at the door, a move for which I am mocked by my brother. I suggest that if this were a speakeasy in 1929 I would have to knock. Still, the door is heavy and metal and other than not needing to knock, it’s lending perfectly to my imagined scenario.

I wonder about the other side of the door. I imagine flappers and bobbed hair, large men in double-breasted suits you didn’t antagonize under any circumstances. Dances from another era, smoke, low conversations at poorly lit tables, jazz.

We push through.

The plan was simple: dress up, eat burgers, drink strong cocktails in unusual locales. We are dressed well: suits – no ties. Polished shoes, gelled hair, mankerchiefs, though we may look cool we sweat. It’s Village Whiskey for burgers and then the speakeasy trail. Three throwback bars from Philadelphia’s own prohibition past: The Franklin Mortgage & Investment Company, The Ranstead Room, and Hop Sing’s Laundromat.

Right now, we go through the unmanned door at The Franklin Mortgage & Investment Company. The décor is cool. Plush brown chairs, sofas, and seats, and a slick bar tucked against the far wall. The lights are low and we find a table. So far it’s meeting my expectations.

Our server comes by; he’s wearing tight brown corduroys, suspenders, a short-sleeved plaid shirt. Black rimmed glasses, a bow tie, and too-neatly combed hair. Bobby. I suddenly realize the music possesses the whiney quality of a band named something like Sadness Café or Emotional Waffles. We look around and understand with horror that we are surrounded by hipsters. They are everywhere. I have doubts.

My doubts are blasted out of my skull by the sheer power of the cocktails. Chris starts with a Jonathon Richman, and I get The Space Between Us – a milky rum and absinthe combo that is like getting a creamy uppercut from Mike Tyson. Then we move to the last page of the menu: I asked her for water, she brought me gasoline. Chris gets an Angel of Mercy and I get a Lady of the Wood, there’s scotch in it, that’s all I remember, even though I am now consulting my notes.

We loosen up and start chatting with Bobby about the ability to tie a bowtie. The guy next to us gets involved; he’s a bowtie guy as well. We share a menu, pay our tab, Bobby brings us two hefty shots of Wild Turkey Reserve. We step out into the chilly night towards our next speakeasy.

Let the games begin.

Chris told me about his plan for a speakeasy night about a month ago. He was so excited, sent pictures, websites, talked about getting dressed up, spending money. It was all so opposite from what I usually do that it actually made me nervous. I am notoriously content to stay near home, hit a small pub, spend two days (read: weeks) in an Italian onesie, read by a fire. I dress for comfort, get home at a reasonable time, never overspend for a drink, and rarely go to a place where I am referred to as sir.

In other words, I have built myself a nice little comfort zone that I rarely leave. And for that reason I was determined to go out and do just that. I was going to enjoy being out, drink things I never drink, go to ritzy places, and say yes to any suggestion which came up. I promised myself.

We are in a back alley known as Ranstead Street. There are dumpsters and the short dingy housing you see at the beginning of an episode of Law and Order. Chris is consulting his map, I look to our right and see it in a hidden black door.


“That’s it,” I say. “The Ranstead Room.”

The Ranstead Room does not, in any way, disappoint my expectations of a 1920s speakeasy. The lights are dim; the walls are carpeted red with paisley, above-lit portraits of nude models sit along the wall. An ancient red chandelier hovers too low, two bartenders – one is pregnant, the other one is bearded and chiseling ice cubes from a giant ice-cube. The music is too quiet to hear effectively, Rom Jeremy’s picture on a door indicates the men’s room. We sit at the bar; look at the one page menu.

Chris: Casino

Damien: Remember the Maine    

We both choose Bartender’s Choice for our second drink as we have a thirty minute walk to our third location and this guy pours heavy. The juices are flowing now, the air isn’t so cold, we are telling funny stories. We are in awesome downtown Philadelphia, people buzzing around us. We get thirsty on the walk, Chris suggests a drink at a high-class joint and we go in. I have thus far kept my promise to say yes to any suggestion.

Del Frisco’s Steakhouse used to be a bank – it has enormous pillars, a long cool bar, and several diners who are clearly using Dad’s credit card for the evening. We pay $13 each for our Tanqueray and tonics and take pictures. We ogle the short skirted waitresses. Chris’ friend Brian has joined us and before we leave we points us to the basement, which is a dining room converted out of the former bank’s vault. We wander down, nobody is there, and that’s when Chris makes the suggestion I knew was coming.

“We need a picture,” he says to Brian and hands him his phone. “Pants down,” he says to me. I have to comply. That comfort zone has been keeping my pants on for too long. Six strong drinks don’t hurt the decision. Brian snaps the picture as a bewildered busboy moseys by.

FLASH 1“Good evening,” I say.

“Hello sir,” he replies.

You have to love the power of a suit.

On our way to the third locale, which ends up being shut down, we run into a gleeful homeless gent. “Get in a picture with us!” Chris barks at him.

“Damn right!” he says. We drop our pants, the man poses in front of us without a skipped beat.

“No, pants down!” My brother insists. The last time we tried to get a person to do a pants down photo with us was in Český Krumlov and it took hours and ended up being vampires. This time, it’s not so hard.

“Sure. $5.” The man drops his pants. In case you’ve ever wondered, homeless men go commando. Chris hands him $10.

We head home on the train, my comfort zone well smashed. I have spent a load of cash, taken a train to and from a bar, my pants have been off, twice, I have posed with naked homeless men, paid $15 for a drink, there have been two speakeasies, talk of bowties, and I have said yes to every suggestion.

We are rolling into Langhorne station, where our mom awaits to bring us on the final leg of our journey. “Hey,” Chris says, “let’s get a sandwich from WaWa on the way home.”


  1. #1 by Jared on January 2, 2014 - 7:23 pm

    There should have been a warning at the top of this page. I am now sitting in my classroom giggling and grinning like an idiot in front of my study hall students (every one of them so obsessed with what is on their phones that they have yet to notice). This sounds like a great night out. I think I laughed out loud when I saw the expression on your face in the pants-down picture. You look like Ned Beatty in Deliverance, and I don’t mean before they met those nice gentlemen in the woods.
    Thanks for the laughs.

    • #2 by Damien Galeone on January 2, 2014 - 8:07 pm

      Thanks, buddy! Oh and squeal!

  2. #3 by Andy on January 2, 2014 - 9:10 pm

    I have no idea why, but when I look at the second picture I’m reminded of a scene in Animal House:

    “Do you mind if we dance with your dates?”

    • #4 by Damien Galeone on January 3, 2014 - 4:12 pm

      Andy, that was basically it. Haha.

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