A Long Weekend in Philly – Historic Walking Tour

Hi friends, welcome back! Every year, Jon and I go on a fall getaway, and this year we decided to spend a long weekend (October 8th – 11th) in Philadelphia. We chose Philadelphia because it’s less than a two-hour drive from NYC, we love learning about history, checking out museums, and surprisingly neither of us had ever been. We also looked forward to running up the Rocky steps and indulging in a Philly Cheesesteak.

Jon and I left on a Friday afternoon, stopped by a cider mill, and then checked into our Airbnb in Old City. I decided to stay in Old City because I figured we would spend most of our time exploring the historical sites, and I’d highly recommend staying in this area on your first trip to Philly. I’d also highly recommend our Airbnb because it was quiet, cozy, safe, had free parking, and extremely walkable to all the main sites. I looked into staying in Center City, but I’m glad we didn’t because the area seems very chaotic and loud.

After settling in, we walked to Oh Brother for dinner and Jon took charge of the ordering. We were both starving so we split a Philly Cheesesteak with American Cheese, Brisket Sandwich, Truffle Parmesan Fries, and Fried Oreos to top it all off! Surprisingly, we didn’t feel terrible after eating all of that. My first Philly Cheesesteak experience was a great success! I know “The Best” Philly Cheesesteak may be a controversial topic, but this one tasted incredibly delicious and the restaurant always seemed busy when we walked by! Oh Brother is definitely not a tourist trap which was what we were trying to avoid.

The next morning, we went to United by Blue for coffee before getting ready for our walking tour. I’d highly recommend taking this walking tour I found on Viator. It lasted about two hours and hit all of the major historical landmarks with quite a bit of humor thrown in. This tour also provided a great history of everything we walked by and gave us a good lay of the land. I highly encourage taking a walking tour at the start of your trip to Philly!

Some of the highlights from our tour: The Arch Street Meeting House built in 1810 as a place for Quakers to worship.

A Ben Franklin Statue next to the fire station he helped create in 1736. Back then it was the first volunteer fire station in America. Ironically in 2013, there was actually a fire at this fire station.

I love the mural outside the fire station.

We stopped by Betsy Ross’s house that has been converted into a museum, but the museum wasn’t included with our walking tour, so Jon and I returned on our second day. It took us about half an hour to walk through the museum and I’d recommend stopping by. It was interesting to learn more about Betsy and see where the first flag was allegedly sown. It was never announced or documented during her time because it would’ve been treason against England. Betsy’s grandson spoke at the Pennsylvania Historical Society in 1870 and told the crowd that his grandma sowed the first American flag, and as they say, the rest is history.

We stopped by Elfreth’s Alley the oldest, continually habited, residential street in America and now a National Historic Landmark. The oldest home dates back to 1703. I love how cute this street is and that it was decorated for fall while we were there. The homes are quaint, but I don’t think I’d want people oogling my house all day long or tour groups outside while I’m trying to watch tv.

Moving along, Christ Church was founded in 1695 by the Church of England as the nation’s first church. They outgrew their space and the church you see today was constructed from 1727-1744. The steeple was funded by a lottery Ben Franklin created and made it the tallest building in America for 56 years. George Washington, John Adams, Ben Franklin, and Betsy Ross even attended some services here back in the day. Currently it’s an active Episcopal parish, but it’s also open to the public as a National Historic Landmark for tours. Somehow I forgot to take a picture of the church, so the below can be found here.

Photo by P. Meyer for Visit Philadelphia

The First Post Office, also established by Ben Franklin who became the first postmaster general. He was clearly a very busy guy 😉

Carpenters Hall served as a key meeting place before the Revolutionary War. In this building the First Continental Congress met, Ben Franklin secretly met with a French ambassador to secure their help in the war, and as one of the first defiance’s of the King, delegates from twelve of the thirteen colonies gathered and voted to support a trade embargo against England. It’s free to visit the small museum inside, but we didn’t make it in during our time in Philly.

The New Hall Military Museum next to Carpenter Hall. This building is a reconstruction of the office of the Secretary of War in 1791. It currently features a museum showcasing the founding of the Army, Navy, and Marine Corp from the American Revolution to the late 18th Century. The museum was closed when we were there, but it sounds pretty interesting.

The tour ended across from Independence Hall so Jon and I ran and grabbed lunch at High Street before we had another tour at Independence Hall. We split a Reuben Pastrami and High Street Hoagie to give us energy.

I hope you enjoyed part one of our long weekend in Philly…stay tuned for Part 2!

34 thoughts on “A Long Weekend in Philly – Historic Walking Tour

  1. You know what? I’ll bookmark this post! This is a very interesting history class with tips in it 😉 Next time I’m going to Philadelphia, I’ll read it so I look smart when I pass by all these places lol

    1. I’m not a history buff so I was proud I could add some interesting facts 😀 you’ll love Philadelphia!

  2. This was a fun one! Philly was one of the places we didn’t make it to when we lived out east. Hopefully someday when we visit again, we can make it here. I’m bookmarking this post for when we do… what you saw is exactly what I’d want to see as well!

    1. Thank you! So glad you enjoyed 😃 I hope you make it to Philadelphia soon, would be a good break from hiking, it’s pretty flat 😂

      1. Haha very true! My fiancé’s family is in CT so we’ll definitely be visiting at least somewhat frequently… shouldn’t be too hard to get to Philly from there.

  3. I’d love to visit Philadelphia sometime and looking at all the wonderful photos from your walking trip wants me to go even more now. Like you though, I wouldn’t want people ogling outside my house and stopping to take photos!

    1. I had forgotten how much history was in Philadelphia and now it’s become a bit of a foodie city too 😃 hope you make it there one day!

  4. You took us on a very interesting tour of Philly – the historical houses are beyond charming and the food scene is clearly worth the visit alone. I’ve just googled Betsy Ross, sounds like an interesting character.

    1. I found out even more about the city while I was fact checking my post 😂 didn’t want to be spreading fake news about Philly! But it’s a fascinating city with a great food scene! You’d definitely like it!

  5. I am still mad at my former employer who always held our conferences in Cherry Hill, NJ, but never ever offered either time or access for a city tour of Philly. So close and yet so far. The city looks beautiful and full of history and you embraced both sides of the Philly Cheesesteak.Hoagie controversy. I think if I lived in Philly, I might have a weight problem. Thanks for taking me to Philly Lyssy. Allan

    1. That is frustrating to be so close but not be able to see the city! You could probably see Philly from your window. It’s a very cool and underrated city, hopefully you make it there one day! I agree it would be hard to resist a daily Philly cheesesteak, at least it has protein… Thanks for reading Allan!

  6. From start to finish on your Philly photo-tour, I was preoccupied with “fried Oreos”. I know people fry just about anything, but the thought of Oreos that way gets a big N-O from me. Having said that, thanks for the photo. They look more appetizing than they sound. Cookies disguised as beignets – heh. You & Jon have cast-iron stomachs!

    1. That’s funny, they were actually very good! I saw on instagram yesterday people are air-frying Lindt truffles. Just when we think we’ve seen it all… We do have cast-iron stomachs ha!

  7. Philly deserves a better reputation for tourism. I love the history and architecture on your walking tour and you always find places with the most scrumptious looking food. Looking forward to your upcoming posts on the City of Brotherly Love.

    1. I agree – it’s a very underrated city! It has so much history and all in such a concentrated area. I had forgotten how much history was there, I even forget how much is in NYC. Food is alway at the top of my planning priorities 🙂

    1. I think it’s more fun to learn about history while you can see the place in front of you too. Glad you enjoyed the tour 🙂

  8. Great post, Philly is on my list to visit when I next come over with work. The history is interesting, and it always make me smile reading when the oldest house is built in the 1700s, because to us in England we have quite a few houses that have been lived in continuously since the 1100s – I think you’d love them. Those Philly cheesesteaks also look INCREDIBLE.

    1. You’ll love Philly and it’s only about an hour train from NYC! Haha the 1700s is practically brand new compared to the places you see. I’d definitely love the homes in England 🙂 So much good food in Philly!!

  9. Can’t wait for Philly Part Two! My friend and I used to meet up there basically annually before the pandemic (her in MA, me in NY) to explore and there is so, so much to do is why we kept going year after year.

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