What To Do in Historic Philadelphia

What To Do in Historic Philadelphia November 23, 2017 · 19 min. readThis article may contain affiliate links.

A few months ago I entered a contest for a trip for two to visit Philadelphia on Two Bad Tourists. Normally contests like this are limited to United States residents so when I saw this one was open to Canadians I jumped at the chance. I've never won something like this before, so I actually forgot about it until I got the emailing saying I had won. Two Bad Tourists then worked alongside Visit Philly to organise the trip for me and my mother to explore Philadelphia for three days. Visit Philly paid for our flights, hotels and gave us a VIP Pass to experience the city to our heart's content. It is thanks to them that this trip is possible.

Several movies and television shows have tried to capture the essence of Philadelphia over the years – from the boxing Blockbuster Rocky, to the paranormal thriller The Sixth Sense, to It's Always Sunny in Philadelphia and even Boy Meets World – but each described the city differently. There is no easy way to approach a city as dynamic as The City of Brotherly Love. With countless layers of art, history, religion and the paranormal, Philadelphia is a city unlike any other throughout the United States. 

Philly Skyline

One thing that surprised me the most about Philadelphia was the history. The city was founded and designed by William Penn, who is also the state of Pennsylvania's namesake. Born in London, England in 1644 he lived through The Great Fire of 1666 and The Great Plague of London from 1665-1666. Both events shaped Penn's life so he designed the city to be strictly stone buildings (to stop fires from spreading) and to have plenty of space between the buildings (as to prevent illness from spreading). This led to the older areas of the city to have winding corridors between old stone walls.

While his design can be found throughout the city, most of it can be seen in the Historic District. This area is full of quirky shops, local restaurants and historic locations like Elfreth's Alley, the oldest residential street in the United States. This alley was first inhabited in 1702, with all the current houses being built between 1728 and 1836. In 1934 a committee preserved the neighbourhood to keep it for future generations. The alley is open all year, but they also put on several festivals such as "Fête Day" in June, "Deck the Alley" in December and various events for Fourth of July, Oktoberfest and Halloween.

Elfreth's Alley Elfreth's Alley Elfreth's Alley

During the 1700s Pennsylvania was one of the 13 Colonies that made up what is now the United States. Prior to the Battle of the Plains of Abraham in Quebec, the 13 Colonies were surrounded by New France to the North and East and New Spain to the South. Once the British captured New France, the colonies had space to grow – and with it came the desire for independence. Philadelphia was the spearhead of this movement with prominent Revolutionaries living here, such as George Washington, Benjamin Franklin, John Adams and "The Little Rebel" Betsy Ross. Their desire for independence would ultimately lead into the Revolutionary War.

As tensions within the 13 Colonies rose, Washington approached Ross in secret and proposed a radical idea. If the 13 Colonies were to be independent, they needed a new flag – and he wanted her to make it.  Although the creation of such a thing would be treasonous, Ross agreed. She then set to work and created the very first American flag, a symbol that stands for freedom around the world centuries later.

Betsy Ross' story is one of American legacy and is known throughout the country, but in Canada it is rarely learned about. Her original house and office where she sewed the first flag – and hundreds more in years to come – can be found in the Historic District. I found the museum to be very interesting and was a great opportunity to learn about Pre-Revolutionary Philadelphia.

Betsy Ross flag Betsy Ross House

If you're interested in Philadelphian history, you'll also want to visit the President's House Site. This is where the original "Whitehouse" stood prior to it being constructed in Washington D.C. and where former US Presidents George Washington and John Adams lived. The site has several televisions, posters and pictures throughout the area that discuss the role of the house throughout the years – and the role of the slaves that lived there during that time period.

Next to the President's House Site is the Liberty Bell Center, which houses the Liberty Bell. The bell is seen as a symbol of freedom throughout the United States and is famous for its iconic crack. It is said this bell rang on July 4th, 1776 when the Declaration of Independence was first signed at the nearby Independence Hall.

Independence Hall

Two other places you'll want to visit while in the Historic District are the Christ Church and the Christ Church Cemetery. The church is a unique example of Gregorian architecture. Following the Dark Ages, the church wanted to open up to new, "enlightened" ideas regarding science and technology. For a brief time period they restyled the windows of churches to be house transparent clear glass – to illustrate the concept of ideas flowing freely in and out – as opposed to the iconic stained glass that only shines light inwards. However, within a few decades of this aesthetic change, the stained glass returned and remains the way it is today. While I've seen my fair share of churches around the world, this is the first I have ever seen with clear glass windows.

Beyond the church is a very small cemetery which holds the graves of several signers of the Declaration of Independence. Although Benjamin Franklin attended this church and signed the declaration, you won't find his grave here. Instead you'll have to walk about 3 blocks east to find the cemetery where he's buried – along with scores of other historical people who helped shape the city and the country. If you have time, I recommend going on the cemetery tour.

Christ Church Cemetery Christ Church Cemetery Christ Church Cemetery

In the centre of the city is City Hall. Construction of this monolithic stone structure started in 1871 and was estimated to be completed in 1876, but it wouldn't be finished until 1901! By the time the building was complete, its architectural style was no longer popular and a discussion was made to destroy it. However, because the building was so structurally sound and was made of such heavy stone, it would cost too much to destroy and thus left intact.

If you're visiting City Hall, give yourself plenty of extra time and take the 90 minute tour of the building. You will learn about the impressive architecture, the history and the legacy of the building. If you're a little more crunched for time, take the 15 minute Tower Tour and visit the top of this building for an excellent view of the city.

City Hall from ground View from City Hall

Regardless of how you explore City Hall, you're bound to hear about William Penn. As the original founder of the city, a statue of him was placed on top of City Hall. At 37 feet tall, this statue holds the record for the largest statue on top of any building in the world! From 1901 until 1987 City Hall was the largest building in Phildealphia due to a "gentlemen's agreement" that no building should be taller than William Penn's statue's hat. In 1987 that agreement was broken by the construction of One Liberty Place. It is said the breaking of this agreement angered the statue of Penn so he cursed all the teams in Philadelphia to never win a championship. After almost three decades of championship drought, a statue of William Penn was placed on the top of the Comcast Building in 2007 – which was then the tallest in the city – and in 2008 the Philadelphia Phillies won the World Cup.

Another location you'll want to visit in Philadelphia is the Eastern State Penitentiary. Opening in 1827 the building was in operation until 1970. Eastern State Penitentiary was the first penitentiary in the United States and coined the "Pennsylvania system", which was a prison system focused specifically on solitary confinement.  Unlike Kingston Penitentiary that I visited earlier this year, ESP believed keeping inmates in isolation would allow them to reflect on their own sins and become better people. Each cell was equipped with one – and later two – skylights nicknamed "The Eye of God" in which would be the only source of light in the cell. This was supposed to help the prisoners reconcile their sins.

Welcome to Eastern State Penitentiary Inside cell at Eastern State Penitentiary Inside another cell at Eastern State Penitentiary

Because the cells were isolated from one another via thick stone walls, men and women could live in close proximity with each other without any problems. Women who had children in prison would be able to raise their child until an "outside connection" could take over guardianship. The longest a child lived in Eastern State Penitentiary was five years.

While the penitentiary house both men and women, it also housed children criminals too. The youngest inmate the penitentiary ever held was a nine year old girl.

Hallways of Eastern State Penitentiary

Although inmates lived in their cell, they could go into the adjacent yard for some fresh air. Here some grew gardens or played with their pets. No two neighboring inmates would ever be allowed outside at the same time as they might communicate with each other. If the inmate ever had to leave their cell a hood was placed over their head so that they wouldn't know where in the building they were.

As time changed, the penitentiary became overcrowded the isolation method was dropped. Newer cellblocks were added and the cells became bigger. Inmates could communicate with each other, and with outside civilians. To try and condition inmates for a life outside of the walls, some were even given jobs inside the prison, such as working as a barber or in the hospital – which was one of the finest hospitals in the city. It was here that Al Capone had a tonsillectomy and, some say, had a circumcision to help clear his bought of syphilis.

Hospital hallway Hospital room Surgery room at Eastern State Penitentiary

Along with Al Capone, the prison would hold several unique inmates while in operation, such as Willie Sutton and Pup, a "Cat-Murdering Dog" (who was actually a dog). As with all stories, those of Pup and Al Capone are questionable in their authenticity. Newspaper accounts say Al Capone lived in luxury with his own private radio, while other accounts say he shared a cell with an inmate. Similarity, Pup's story of being a hard convict with a life sentence is probably based in fiction and was instead just a dog donated to the prison to help with inmate recovery.

Al Capone's Cell

The story of Al Capone has a paranormal side to it as well. Although Capone was imprisoned for concealing a weapon, he was also responsible for several murders, including the Saint Valentine's Day Massacre. During the Massacre a man named Jimmy Clark was killed. It is said that while inside his cell at Eastern State Penitentiary, Capone could often be heard screaming, often telling somebody named "Jimmy" to leave him alone, and many believe this was Jimmy Clark. It is said that Jimmy followed Capone after he was released from Eastern State Penitentiary in 1930 and continued to terrorize him both at home and later when he was imprisoned in Alcatraz.

It's important to mention that Eastern State Penitentiary had some dark moments during its existence as well. The prison used different torture techniques on some of the prisoners, such as dousing them with water and leaving them outside overnight in the winter, or using a metallic mouth-grip that would clamp down on their tongue. Eastern State Penitentiary also used "The Hole", an underground isolated cell with absolutely no sunlight or human interaction. At times prisoners would spend up to a month down there.

The Hole

Eastern State Penitentiary also had various riots, murders and suicides. If you include the rounds of tuberculous, influenza and infection that prisoners suffered from while it was in operation, over 1,000 people are said to have died within its stone walls.

While Eastern State Penitentiary's purpose was to "heal" their prisoners and help them become functioning civilians, this can't be said for all the prisons in Philadelphia. Across the city is the infamous Holmesburg Prison. It was here various human experiments occurred on the patients. This included everything from chemical experiments to radioactive treatments and even the sewing of arms, legs and organs from cadavers to living patients to see if they would reanimate. Unfortunately, I did not have the chance to visit Holmesburg Prison while I was in Philadelphia.

Not far from Eastern State Penitentiary is a much more pleasant location, and one of the most popular icons in Philadelphia, called "The Rocky Steps". Made famous for their role in the 1976 movie Rocky, the steps have become an icon for underdogs rising up to meet their challenge. Since Rocky Balboa climbed those stairs 40 years ago in preparation for his fight against Apollo Creed, they have become one of the city's most popular tourist attractions, with throngs of tourists climbing the stairs and posing for pictures at the top every day. Even the footprints where Rocky stood that cold November morning in 1976 have been cast in metal at the top of the stairs and a statue of him was placed near the base. For outsiders, the city's love for Rocky may seem a little extravagant, but City Commerce Director Dick Doran once said Rocky had done more for the city's image "than anyone since Ben Franklin" so the love for him is plenty justified.

Rocky Steps Rocky Steps Rocky Steps

There's much more to see and do while in The City of Brotherly Love than what I mentioned in this article. You could eat a Philly Cheesesteaks at Geno's, shop for fresh fruit in the Italian Market, visit Mac's Tavern from It's Always Sunny in Philadelphia, stop by the scores of museums and art galleries, go visit the 8,000-plus public murals, gawk at the Magic Gardens or just wander the streets. Philadelphia has been ranked one of the top cities to visit in the United States and is recognized worldwide as being one of the most LGTBQ friendly cities. It's a city for everyone – from those who love movies, history, music, art and everything in between. If you're planning a visit to Philly, I'd recommend Visit Philly's overnight hotel package, as it's the perfect way to explore the city.

Geno's Cheesesteaks

What would you do if you won a free trip to Philadelphia? Tell me about it in the comments below! 

Don't forget to pin it!

What To Do in Historic Philadelphia What To Do in Historic Philadelphia What To Do in Historic Philadelphia What To Do in Historic Philadelphia

And, as always, a big thank you to my sweetheart Jessica Nuttall for proof reading a countless number of my articles. I couldn't do any of this without you. I love you.

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