Near Death Experiences in the Pyrenees, Salvador Dali & Preserving the History of America

Word on the Street: 8 Questions with Jason Sherman

In each edition of “Word on the Street,” we interview a Guide to learn about their Sidewalk and some of their best travel stories.


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Meet Jason Sherman, filmmaker, tech entrepreneur and Wharton instructor. He dishes on the importance of the oldest bridge in America, the power of film and the wonder of theme parks.

1. You just published Kings Highway | Holmesburg Tour. What is your Sidewalk about?

The Kings Highway was a 1,300 miles colonial-era road that connected Charleston, South Carolina to Boston, Massachusetts. It was ordered by King Charles II of England. Construction started on it in 1650 and took 85 years to complete.

My Sidewalk is about how one of the many neighborhoods in Northeast Philadelphia along the Kings Highway played an outsized role in American history. In addition to taverns and inns, the Holmesburg section of the highway features the oldest bridge in America, ordered to be built by William Penn.

2. If there is one thing that you want people to get out of your Sidewalk, what would it be?

If you want to understand the origin of America, you have to look beyond the big cities. A visit to Olde City in City Center Philadelphia doesn’t tell the whole story. It is in small neighborhoods  where the Founding Fathers decided who should write the Declaration of Independence, and who should sign it.

Of course, these neighborhoods are slowly disappearing or reinventing themselves. So, these special historical places will either dissolve into the forgotten memories of time or emerge as iconic places to learn about our nation’s history.  

3. What is your favorite stop on the Kings Highway | Holmesburg Sidewalk?

The King's Highway Bridge. This stone bridge dates back to 1697 and still stands over the Pennypack Creek in part thanks to a recent $3.2M renovation.

Everyone crossed that bridge. If you were going back and forth between Philadelphia and New York, you crossed the bridge. The only way you wouldn't go over it is if you decided to dredge through the creek, and get your feet wet. The bridge served as a critical piece of infrastructure for people with names like Thomas Jefferson, Benjamin Franklin, John Adams and George Washington.

When you see it, you can almost hear the soldiers of the Continental Army marching over it en route to Yorktown for their victory over the British.

 Construction of King's Highway Bridge in 1697

Construction of King's Highway Bridge in 1697

 King's Highway Bridge, before renovation.

King's Highway Bridge, before renovation.

4. You created a documentary about the King’s Highway. How did you become interested in the topic?

I took a break from filmmaking to work on a few tech startups, teach entrepreneurship and watch a lot of documentaries. One day I happened to see an article about indigenous tribes in Pennypack Park - which is located in present-day Holmesburg. The Native Americans used the King’s Highway to travel to Center City to meet with William Penn.

This got my wheels turning and I started doing research, unpacking the history of this area, and meeting with people in their 60s and 70s who had written books about Holmesburg and other neighborhoods. When I saw building after building get demolished, I knew I had to tell the story of this place before all signs of it disappeared.

5. Why create a documentary? How has the King’s Highway documentary been received?

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As a medium, film sticks in people’s memories. People remember specific parts of movies forever - whether it is Pulp Fiction or Star Wars. I want to create content that sticks with people, and can impact behavior and thoughts.

I completed the The Kings Highway documentary at the end of 2016, after a year and a half  of filming, interviews, and editing. For me, the journey of the film is ongoing. There are still showings, and interest in the documentary is growing. People are buying the DVDs, t-shirts and merchandise, and I look at the shipping addresses - they aren’t just in the Philadelphia-area or the northeast - they are from all over the country. The Kings Highway is a national story because it is integral to the history of the country, and it is a part of the story that no one knows about.

6. If you could travel with anyone in history, who would you travel with and where would you go?

 Salvador Dali

Salvador Dali

I’d go to Barcelona with surrealist painter Salvador Dali. My mother is from Barcelona and my uncle, who was an attorney, was a friend of Dali’s and gave him legal advice. So growing up, I used to hear these wacky tall tales about the artist’s playboy lifestyle. I actually remember visiting Barcelona and seeing him with his iconic mustache signing lithographs.

I would love to just join Dali at his Barcelona haunts: chat with him and his artist friends at an absinthe bar, smoke cigars on the beach, drink cortados and carajillos at cafes, snack on tapas, and sketch some scenes in Guell Park together.

7. Do you have any travel nightmare stories or trips you wish you could take back?

When I was 13 years old, I went camping in the Pyrenees Mountains - my first camping trip outside of the US. One night while sleeping on a plateau, we felt an earthquake. The shaking kept going and getting stronger. When we unzipped our tent door, we found that we were in the middle of a cattle stampede. All these cows were running past our tent; we could have been trampled to death.

The next morning, a pair of goats chased after me when I tried taking their picture. I booked it along a riverbed, when one of the people on our trip yelled, “watch out for the snake holes” - apparently there are snakes in the Pyrenees.

The goats finally gave up and I made it to a rock without encountering any snakes. I took a seat to catch my breath and appreciate the fact that I was still intact. Then I felt a burning sensation on my legs. I was covered in fire ants.

That was the last time I went camping. I now put a very high value on comfort when I travel.

8. What is a destination that you’re embarrassed to admit that you love?

Universal Studios is my guilty pleasure . . . actually I’m not that guilty about it. It’s a weird place for me to love, because I don’t even do roller coasters.

What I love is the feeling of being transported to a magical place. After a few days there, you feel completely disconnected from the real world. This fantasyland has perfect weather, bathrooms everywhere, and plenty of spots to grab a coffee. But more surreal is this amazing experience you have with complete strangers. Where else can you be around people who are as excited and in awe as you are? It’s an incredible feeling.


For more on Jason, check out The King's Highway documentary and follow him on Twitter.


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Corey Wood, Product Lead - Growth & Lifecycle

This interview has been condensed and edited.

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