On November 6, 2015, the city of Philadelphia was awarded the distinction of being the first World Heritage City in the United States. Democracy was born in Philadelphia and it’s where the Declaration of Independence was signed – two important enough reasons to justify adding Philadelphia to the list of World Heritage Cities, right alongside critical cultural centers like Rome and Cairo.
Historic sites like Independence Hall were a big draw to Philadelphia for Mom and me as we made our first trip there this past October. We visited all the main historical attractions and I can fully understand how and why Philadelphia has been named a World Heritage City. It was surreal to stand in the same room where the Declaration of Independence was signed and to see the exact chair George Washington was sitting in when it all went down. But Mom and I ventured a bit further down the timeline and discovered a few other places that also contribute to the historic appeal of Philadelphia. The following three Philadelphia architectural sites are quite historic, are masterpieces of varying degrees, and all are absolutely worth a visit.
Philadelphia City Hall
It is the largest municipal building in the United States and I could not get enough of it. Philadelphia City Hall is majestic and is visible from almost any point in Philly. I initially spotted the building when Mom and I set out down Benjamin Franklin Parkway to explore on our first day in the city. I tried to photograph the building from every angle and that proved to be a challenge from street level, as it’s a bit imposing. It used to be the tallest building in all of Philadelphia, the top of which is adorned with a 27-ton statue of William Penn. After three days of admiring City Hall, on our last morning in town, Mom and I decided to take a tour to the building’s observation deck. Timed tickets are required to go to the top of the tower and we had some time to kill before our tour, so I wandered the courtyard and alcoves. The enormity of the building and its dramatic Second Empire-style architecture might cause some visitors to think they’d been magically transported to an opulent European palace.
TIP: Visitors can ride up to the observation deck but there are a limited number of tickets available for the timed tours. Purchase tickets ahead of time at the Visitor Center. Interior tours also are offered Monday through Friday at 12:30pm.
The Grand Lodge of Free and Accepted Masons of Pennsylvania
I did not expect to be as wowed as I was by the Masonic Temple. It’s right across the street from City Hall so Mom and I figured, why not – let’s have a tour. Plus, the legendary secrecy of the Masons has intrigued me for years so I thought maybe I’d gain some insight to this private fraternity. (Spoiler alert: no such thing happened.) Anyone even remotely interested in architecture needs to visit the temple. The exterior resembles a Norman cathedral; the interior is a visual wonderland. The temple was completed in 1873 after five years of construction and $1.6 million of funds. The hefty sum is one indication of how ornate the temple truly is.
The guided tour takes visitors to seven main rooms, each with a different architectural style. And these aren’t just “rooms”; they’re vast gathering halls where Masons do the secret stuff that Masons do. Even the foyer and the staircases are works of art, adorned with ancient inscriptions, flanked by marble statues, and presided over by stained glass windows. I’m still not exactly sure what goes on in that building and what Masons do, but the temple is magnificent.
TIP: Public tour dates and times are a bit scattered, and the lodge may close for private events, so be sure to call or stop in ahead of time to double check availability.
Eastern State Penitentiary
I don’t know how, but I managed to convince my mother to visit this former prison complex and world’s first penitentiary. Opened in 1829, Eastern State Penitentiary (ESP) was unlike all other American and European prisons. Its practices and philosophies broke away from corporal punishment and aimed to move the prisoners towards spiritual reflection and change. Solitary confinement, or “The Pennsylvania System”, was the norm at ESP and human interaction for prisoners was minimal. ESP was built on the premise that prisoners, when left alone in silence with only their thoughts, would realize the repulsiveness of their behavior and their crimes, therefore becoming penitent (source of the word “penitentiary”). The architectuctural design of the prison was intentionally aligned with the philosophies of The Pennsylvania System. Architect John Haviland designed it so that long corridors of cells, like spokes of a wheel, branched out from a central surveillance rotunda. The cells’ vaulted ceilings and the high, arched windows throughout the complex are reminiscent of grand cathedrals – and that was Haviland’s intention. The prison was meant to be perceived as a forced monastery from the inside, while the tall, imposing Gothic walls on the outside gave the illusion that something very evil was taking place within.
The prison officially closed in 1971 and opened for tours in 1994. ESP currently is operated by the non-profit, Eastern State Penitentiary Historic Site, Inc., and is still open for tours. Visitors are supplied with an audio guide, narrated by actor Steve Buscemi, and have the opportunity to physically enter some of the cells. ESP was home, for a short time, to one very notorious individual: Al Capone. Visitors can look in on his cell, which is set up much the same way it was when Capone did his time at ESP, and see that he was afforded some very special treatment.
TIP: Eastern State Penitentiary is located in the Fairmount neighborhood, a bit of a ways from Center City. Ride the Philly Phlash to ESP for only $2 (per ride) or $5 for an all-day pass. Hop on at one of the Center City attractions and get dropped off/picked up right across the street from ESP!

Big thank you to Visit Philly for providing complimentary admission to Eastern State Penitentiary and for the Philly Phlash passes. They really came in handy! As always, all thoughts and opinions are my own.
Thank you so much! I am off to Philly today and this list has given me some great ideas!
This is great! pinning for our spring college tours trip!!
Hoping to go to the prison next time I’m in Philadelphia. Thanks for sharing!
Didn’t know that about the Declaration of Independence – the Rome of the States (or as a Greek I’d argue perhaps Athens instead for the analogy ha ha ha). What was it like being in a former prison?
I’ve been planning on visiting Philadelphia, so this info is really helpful. Look forward to exploring these sites. Thanks.
Philadelphia is one city that is on my bucket list, after reading your blog, will make a trip when it gets warmer, City Hall State Penitentiary and The Grand Lodge will be the first things to see on my list!! Thanks!
I have been to Philly, but have never gotten the opportunity to really explore it. Will have to check some of this out. The Masons building looks beautiful.
Philly is a great city! It really surprised me when we were there a few months ago. We did an open top bus tour and I was enthralled by the amount of historic buildings and homes in the city.
All these buildings look gorgeous! I used to live near Philly and had been there often, but never been to any of these. Would love to if we go back again 🙂 such stunning architecture!
I really enjoyed it when I went to Philadelphia, but didn’t make the penitentiary. I’ve long wanted to go back – this has reminded me of how much!
What an interesting city and diversity of architecture. Some of it looks very European doesn’t it? My father was a Mason for many years and we never knew what he got up to so I’m not surprised you didn’t get any better understanding
Truly these places should not be missed. I want to visit there soon.
I have never been to Philadelphia, but it’s definitely on my list. I love architecture and all of these places look amazing. Here’s hoping I get there sooner than later!
I always chuckle that an old prison is at the top of everyone’s list of places to visit…but then again…so is Alcatraz in San Francisco. With everyone being so impressed by it, I’ll have to check it out myself someday.
I find architecture really interesting because it can tell you so much about how people thought about life and culture at the time when the structure or building was created and it is really fascinating to see what the preservation of the Eastern State Penitentiary can tell you about how people viewed criminals and the philosophy surrounding crime and punishment back then. Thank you so much for posting this. I love it when people post about the unexpected but nevertheless still fascinating things to see when travelling. Doesn’t it say a lot about how we think about trade, tourism and travel nowadays that we are not surprised by the fact that local and state government bodies will say yes to opening up such places as tourist attractions? That fascinates me too.:)
I had no idea the buildings in philly are so gorgeous!! Will have to pin this for a future trip there!
I literally laughed out loud about the Masons doing their secret Mason things. I’ve wondered about their organization, too. I’d love to tour all three of these buildings. The Masonic Temple because it intrigues me, City Hall because it looks stunning and very reminiscent of a fairy tale castle, and the penitentiary sounds creepy and cool to see where Al Capone was imprisoned. Capone sees like a man who could get what he wanted, even from prison, so I’m guessing he had the room with the nice wooden furniture, lamps and painting. Am I right?
I love the history of the penitentiary. It’s crazy to think that it was still open not too long ago! And I find the contrast of the architecture of the inside and outside really fascinating.
I’ve only been to Philly once (about 15 years ago) and didn’t get to visit any of these. Looks fun. I’d really like to do another trip to Philly and definitely want to see some of the museums.
It’s always fun to see my city through fresh eyes.
Philly is easily one of my favorite cities, but I took the food and drink side of it the last time I was there. I’d love to explore these sites, especially Eastern State Penitentiary – it looks so cool inside! Thanks for sharing these! Hopefully, we get to travel together in 2016. 🙂
Very interesting. My dad actually performed at ESP when he was a child in the 1930’s/1940’s. It is funny to think of a little guy putting on a show in that creepy place. He became a cop haha.
Never been to Philly, but these places definitely make me want to go. The history of the jail sounds interesting. I wonder how effective their techniques were compared to other prisons and prisons of today. I would imagine they had mixed results depending on the inmate.
I think the city hall is a very beautiful building. It’s time to head back to Philly!
city hall is seriously a beaut. i love walking through it at night and seeing it lit up, especially in the winter when they have the ice rink set up outside! one of my friends actually got married outside of there, and it was amazing!
Wait, there’s an ice rink?! Where? In the courtyard area? I’d love to see that!
This is a great post! Philly has so many cool things to offer and these are just the tips of the iceberg ! The Masonic Temple is considered the Grandest in the world, although London and Stockholm are supposed to be pretty close. If anyone would like to see a bit of it on the inside you can check out “Expedition Unknown” on the Travel Channel, season one, episode eight, about the alleged “Beal treasure”. The host , Josh West came to Philly as part of that show, I yours truely got to show him through the building. The Temple portion starts at about 23 minutes or so.