But ultimately, I looked in the mirror, told myself to stop having foolish dreams, and get a real job.  So that is what I did.

Then at my 40^th birthday, where you can see below I was enjoying myself already, my brother told me he had organized a historical drinking tour of Philadelphia through Grim Philly tours. It combines two things I love – drinking and history! 

This niche tour company focuses on the true crime and Prohibition era in Philly.  And it is run by history professors and high school teachers… just like I once dreamed of becoming!  When I heard that, I was excited. This wasn’t going to be a History Channel alien hack show.  This was going to be the real deal. 

As an added bonus, they even agreed to customize the tour to my interests!  This was a hard choice for me.  Do I ask to tour Socialist Party gathering places during the Gilded Age?  Or maybe drinking establishments opened during the Spanish Flu outbreak?  I realized requests like that would make me out to be a douche and a dick, so I asked for something else: tell us about how people drank in Philly back in the day.

On the day of the tour, we were set to meet Ted, our tour guide, upstairs at Rotten Ralph’s, located at 2^nd and Chestnut in Old City.

We imbibed a bit downstairs before we moved upstairs to begin our tour.  You should definitely ask for Ted when you organize your own tour.  He is a high school history professor in Jersey, really knew his stuff, and makes sure that he keeps everyone engaged and interested.  Just be prepared for some blue language as well! We knew that ahead of time and we were ok with it, as you might have guessed.

After we got settled with another round of drinks, Ted began regaling us with some of the drinking history of Philadelphia.  We discussed the more well-known drinking spots, like City Tavern and Tum Tavern (birthplace of the Marine Corp). But he also told us stories about some of the more infamous places along Front Street that were frequented by Philly ne’er-do-wells during the early days of the city. Not the drunken idiot Eagles fans you find nowadays: pirates, murderers and all kinds of other creeps.   

During this, we learned a lot about things left out of your history books.  For instance, you may have already known that there is a lot of doubt that Betsy Ross really created the first American flag.  But what you may not have known is that she was considered a major babe and married at least two pirates / privateers!

After about 30 minutes of the stories, we took a break for the most important part of the tour: the drinks.  Our tour guide began pouring everyone a glass of wassail, an English Christmastime drink made from apples.  It was a pretty tasty drink – warm, cidery and delicious. Almost more like a warm cider than an alcoholic drink.

After our drink break, we listened to a few more stories about the seedier sites that used to exist along Front Street and the Delaware River.  Then, back to more drinks: shots!

It was about this time when we moved along to the next stop on our tour: Infusion Lounge, also on 2^nd Street.  This was a former speakeasy, which made the perfect segue to our discussions on Philadelphia during Prohibition.  Philly did not have a very good reputation in those days: there was a high level of corruption among the city police officers, and those reformers that did come in were chased out for trying to do too many revolutionary things: like enforce the law.  We also learned about some of the gangsters that were running the show: a Jewish businessman who kept in the shadows, a Polish guy who pretended to be Irish, and (my favorite) a hunchbacked midget who moonlighted as the mascot of the Philadelphia Athletics.

While we were at Infusion, some of our group enjoyed the cigars that were available for purchase there. We also heard an interesting ghost story complete with photographic evidence as shown by Ted. 

After a few drinks at Infusion, we went over to Christ Church, just off 2^nd and Market Street.  We may have had a few drinks passed around as we were hearing stories about the history of the church, but I won’t confirm that.  What I can tell you is that this church has an interesting story.  Besides being the final resting place of one of the Founding Fathers, it was also the place where some unlucky saps met their final demise (luckily there is a cemetery right next to it).  The first story involved someone unlucky enough to have fallen into one of the crypts, and then having locked themselves in there.  Story is, some people heard screams for help, but had no idea where they were coming from. Only years later when some of the groundskeepers were going down into the crypt did they find the remains of someone not where they were supposed to be!

The second story involved the bell tower.  When the bell tower was added to the church, it became the largest building in colonial Philadelphia.  Anxious to show off their fancy new bell, the bell ringer went up to the top of the tower and began pulling the rope…but forgot to let go.  And then he went tumbling out of the opening to his death.  At least he landed in the cemetery, so they wouldn’t have to move him very far.

We got the impression the Church itself does not like to advertise these stories, so don’t ask about them if you ever go there.

After those uplifting stories, we went to our final stop – JJ Bootleggers, also on 2^nd Street.  Our group had a section reserved for us, as well as a round of drinks waiting.  Ted then regaled us with a few more stories of Philadelphia, and we also had the chance to chat with him one on one and ask for more detail on some of his stories.  We hung around for awhile here, getting some dinner and a few extra drinks before we left.  I definitely recommend trying out their cheese steak. The atmosphere in this bar was very cool, and if you go their hallmark drink is the moonshine, which seemed appropriate for the theme.

Besides the storytelling and tours, Grim Philly also provided us with several drinks at each of our stops.  And if that is not enough for you, additional food and drinks can be ordered at each of the bars you visit.  Since it was my birthday, I was able to guilt people into getting me something everywhere.  And I bought myself a few as well.

The Grim Philly tours are not good for kids, but you probably already figured that out on your own.  There is drinking, foul language, and (depending on the tour you choose) lots of talk about sex, murder and other vices.  But it is a great time for the adults!  You get to learn a little about the wonderful city of Philadelphia, maybe find some new watering holes, and get a chance to hang out with your friends and family.

So what are you waiting for? Head on over to their website, find yourself a tour (or reach out and organize your own).  The tour guides are great, the subject matter is interesting, and there are drinks to be had! 

-Shawn