A local’s guide to Old City, Philadelphia

April 26, 2018
Ben Caplan

No one knows local life like our guides. That’s why we’ve asked them take us around their favourite ‘hoods and offer their insider tips on seeing the city like a true local. If Old City sounds like your kind of place, local Philadelphia guide Ben and his team can show you around the district on their History in HD tour.

Old City’s main draw is its history. It’s the most historic square mile in America. But there’s way more to it than that. There are great bars and restaurants and beer gardens and art — not to mention the best cheesesteak in Philadelphia.

People ask me all the time if I was a history major in college. Ha! I was never especially interested in history growing up, and I am hardly a history major. I think however, I speak with a passion that comes from trodding the same cobblestone streets as Ben Franklin and George Washington. Knowing that great important things were done in this square mile that that I call home adds some reverence to my daily routine. Living history is a lot more fun than studying it.

narrow street between old buildings in Philadelphia

Take in America’s history on a trip to Philly | Photo by Philadelphia Urban Adventures

Why you should visit Old City

To appreciate the history of America

See where the country was founded and learn a little about what it took to create this nation.

To eat good food and drink good beer

Old City was a busy industrial port for most of our history, but now it has found new life in its cuisine and wonderful drinking establishments.

To see the architecture

Old City is a nice mixture of contemporary and classic styles of architecture: Greek revival displayed in Chestnut Streets banking district, Colonial trinity’s on Elfreth’s Alley, the tallest Skyscraper in the country… in 1810.

My top 10 things to do in Old City

Speak with Neil at Christ Church

Christ Church is my favourite place in Old City. (Keep in mind that is coming from a non-religious, Jewish person.) It is the most historic place in Old City. Only two buildings can claim to have held all 56 signers of the declaration of Independence, Christ Church, and Independence Hall. Independence Hall is great, but it’s a museum; Christ Church is an active church that hasn’t missed a Sunday service in 322 years. Go there, and ask them to show you to George Washington’s pew. Or perhaps you’re a Franklin fan? He sat there as well, they all did.

If you are lucky enough to be there on a day when the curator, Neil, is there, pick from the wealth of his historical knowledge. Just start by telling him where you are from, and I guarantee he will have an interesting story to tell you, and he speaks with a reverence that makes the hair on the back of my neck stand — and I see him at least three times a week.

Over one million people go to see the Liberty Bell every year (as you should). I like to tell people to stop by Christ Church on a Sunday and listen to their bells. Each one is about as old as the Liberty Bell, and made in the same foundry in London, one is even a twin of the Liberty Bell. All eight of Christ Church’s bells were rung on to celebrate Independence, and you can still hear the exact same sounds Jefferson, Franklin and Hamilton heard on July 8th 1776.

exterior of a church in Philadelphia

Be sure to visit Neil at Christ Church | Photo by Philadelphia Urban Adventures

Eat at Sonny’s Cheesesteaks

Sonny’s doesn’t necessarily boast the same name recognition or history as Pat’s, Geno’s or Jim’s. However, if you are going strictly for overall taste, I believe that you should pay my friends at Sonny’s a visit. I order my cheesesteak “wiz-wit.” That is Cheese Wiz, with fried onions. It’ll come on a fantastic Amaroso’s hearth baked roll, in a brown paper bag with grease soaking through.

Visit the Benjamin Franklin Print Shop/B. Free post office (322 Market St)

On Market Street, in between 3rd and 4th streets, is where Benjamin Franklin lived. Unfortunately, we lost his house to the mists of history, but we still have the post office he owned and operated, The B. Free Franklin Post office. It is still an operational post office, so you can send a postcard to yourself or a friend, and it will arrive with Ben Franklin’s signature as the cancelling stamp — an ode to when he, as postmaster, would’ve signed over each stamp that had been used.

Right next door is the Franklin Print Shop. Franklin was a printer by trade; it’s how he made his money and gained his initial influence. This is not his actual print shop (his was about two blocks away) but it’s a damn good replica, and if he sprung to life today, he could start printing The Pennsylvania Gazette as he did over 200 years ago. The National Park rangers who run the print shop give a wonderful demonstration of how 18th-century printing works. As a bonus, you can pick up one of the cheapest, coolest souvenirs in town: a replica print of The Declaration of Independence that was printed (most likely the previous day) in that print shop ($3). They also print and sell other famous quotes and letters from revolutionaries. I like to combine the two stops, because you can send some of the prints to friends and family at the post office, for an ultra-historical and ultra-affordable souvenir!

Throw pennies at the Philadelphia Mint/Franklin Grave (5th and Arch St)

Follow me on this one: at the corner of 5th and Arch streets is both the Philadelphia Mint (largest coin factory in the world) and Benjamin Franklin’s grave. We throw pennies on his grave because he said, “A penny saved is a penny earned.” Which admittedly makes no sense, because he wanted you to save your pennies, not throw them onto a dead man’s grave. (The pennies are used for upkeep on the grave site.)

The mint is a great place to go, especially on a rainy day. It is a self-guided tour over the production floor, where you get to see the actual minting of our coins, with the process explained step by step. Best part is the tour is free! All you need is your ID.

Now, here’s where the whole experience comes together: in the gift shop of the mint, there is a change dispenser. You put in a dollar, and receive four quarters fresh from the most recent minting. Take a quarter from the mint right across the street, make a wish, and toss it on Benjamin Franklin’s grave.

Drink (and eat) at Khyber Pass Pub

I would be surprised if a resident of Old City gave any other answer to the question, “Whats the best bar in Old City?” Khyber Pass is a mystery wrapped in an enigma. No you wont find traditional Afghany food here. It’s an old punk rock venue with craggled facade, turned Cajun Pub, with a great rotating beer list that is equal parts local favourites and international intrigues.

Pressed metal ceilings, a rock ‘n’ roll juke box, and a relaxed informal vibe are welcome to a neighbourhood consisting largely of fancier and more expensive establishments. Oyster po’ boys, fried green tomato BLTs and mint juleps will have you feeling like you’re in NOLA rather than PHILA. Oh, and did I mention the bacon grease popcorn?

exterior of an old pub in Philadelphia

#localsknow this is the best pub in Old City | Photo by Philadelphia Urban Adventures

Hang in a hammock at Spruce Street Harbor Park

A new addition to Old City, Spruce Street Harbor park is the best place to spend a summer evening. On Philadelphia’s historic waterfront, known as Penn’s Landing, is an oasis of food stands, hammocks, board games and dazzling lights that make the park glow like a rainbow.

Spruce Street Harbor Park addressed the issue of our largely unoccupied waterfront. A couple years ago, the Delaware Waterfront Company decided to spruce up the area a bit. At the park you’ll find food stands made from converted shipping containers, a floating beer garden, tons of seating and hammocks! About a hundred of them, but good luck getting one — you must have keen eyes and quick feet, because after dark the park is the place to be.

Indulge your sweet tooth at Shane Confectionary

Did the six cheesesteaks you ate give you a hankering for something sweet? Head over to Shane Candies for equal parts history and confectionary. At 110 Markets Street, it is the oldest candy store in America, opened in 1863.

Grab a beer (or two) at Independence Beer Garden

Enjoy local beer and tasty snacks right across the street from the Liberty Bell, and in the shadows of Independence Hall and Congress Hall. It’s no secret the founding fathers loved beer, if they were here today, I imagine they’d stop by quite a bit after Congress gaveled out.

tour guide in front of a bridge in Philadelphia

Take a tour of Philly with local guide Ben | Photo by Philadelphia Urban Adventures

Hang out at Paddy’s Pub

This hole-in-the-wall pub was the inspiration for Always Sunny in Philadelphia, one of my favourite TV shows.

Practice free yoga on the Race St Pier

Race Street Pier was made from recycled and reused materials back in 2011. From April to October they offer daily free yoga classes in the mornings and evenings. I live right across the street and it’s so pleasant to walk across and do yoga, for free, while taking in the beautiful Delaware River.

How to get to Old City

Old City can be accessed a couple different ways. The subway stops at 2nd Street, and 5th Street on the Market Frankford (Blue) Line (we call it the “El”).

Philadelphia is relatively drivable, but parking can be difficult. I would set your GPS for the Independence Visitors Center at 6th and Arch streets. They have a reasonably priced underground parking garage.

About Ben:

Hey! My name is Ben Caplan and I am a guide for Philadelphia Urban Adventures. My start with Urban Adventures actually came as a customer. My Mom got me a tour for my birthday after I had moved back home to Philadelphia, after six years on the west coast. I wasn’t exactly ecstatic when I received the gift voucher in my email — I was not a “tour person.” Long story short I had a BLAST, and realised that tours don’t have to be dry, backwards-walking, umbrella-holding, scripted, big group hell. There’s a better way to do it. Walk the backroads, pull on some doors, talk to the locals. Experience the city like a local. Five minutes after my tour I asked for a job. It’s been two years now, and I give every tour we do here. I live in the neighbourhood that my tour showed me. Needless to say I believe tourism can make a big difference in someone’s life.


History in HD

Visit those unmissable Philly sights on this historical Philadelphia tour that ditches the guidebooks and gives you a dose of history from a local perspective. After all, this is the history that shaped the people of this city, so why not learn about it from them?