I Visited Philadelphia on a Rainy Weekend. It Wasn’t What I Expected
Checking off more of the East Coast with a late-night arrival, a Hilton stay at The Inn at Penn, a Delaware day trip, crab cakes, the Liberty Bell, and Independence Hall.
Philadelphia was one of those trips where the weather set the tone before the city even got a fair chance.
I visited on a rainy weekend in April, flying in from Dallas after work on a Friday night and staying until Sunday. By the time I landed at Philadelphia International Airport, it was around 11:30 p.m., and by the time I made it to the rideshare pickup area, it was basically midnight. I was tired, it was cold, the rain was starting, and I was immediately reminded that late-night arrivals can make even a good city feel rough at first.
I chose Philadelphia because I wanted to start checking off more of the East Coast on my 50-state journey. I had heard good things about the city, especially that it was a more manageable East Coast urban destination than New York. I thought it might be a better fit for someone like me who likes people, wants to take things slowly, and usually connects more with places that feel a little more relaxed. I also wanted to visit because of the history. With America approaching its 250th birthday, Philadelphia felt like one of those cities I needed to see for myself.
And, of course, I wanted to try one of Hilton’s best properties in Philadelphia: The Inn at Penn.
A Rough Late-Night Arrival in Philadelphia
My first impression of Philadelphia was honestly tough.
I flew Frontier into PHL, and the airport felt disorienting to me, especially trying to get from the gate to the Uber and taxi pickup area downstairs. To be fair, it was basically midnight, I was exhausted, and I was arriving after a full workday and a flight from Dallas. But even with that in mind, the airport felt like it needed a refresh. The internet was also basically inoperable the entire time I passed through, which made something as simple as downloading movies more of a project than it should have been.
By the time I got outside, it was cold, rainy, and not exactly the kind of welcome that makes you fall in love with a place immediately.
That was my first real reminder on this trip that East Coast cities move differently. They feel older, faster, denser, and a little more intense. Coming from recent trips out West and in the Southwest, that was a major shift.
Staying at The Inn at Penn
I stayed at The Inn at Penn, a Hilton Hotel, located on the campus of the University of Pennsylvania in University City.
As many of you know, I am a Hilton loyalist, and I was not going to pass up the chance to stay at one of Hilton’s stronger Philadelphia properties. The hotel seemed to be going through some kind of lobby renovation while I was there, but based on the sketches of what it should look like when completed, I think it will turn out great.
The check-in process was fine, especially considering how late I arrived, but the front desk service left a lot to be desired. It was not a very warm welcome. Barely a hello, honestly. After a long travel day, that stood out.
Once I got past that, though, the actual stay was much better. The rooms were comfortable and had the more polished feel you would expect from a four-star Hilton property. I ordered room service numerous times, and that was solid. The bed was comfortable, the room felt upscale, and the location was excellent if you want to be near Penn, Drexel, nearby restaurants, and University City.
That said, if you are visiting Philadelphia and want to be right in the middle of the city’s historic core or closer to the hustle and bustle of Center City or Old City, I probably would not stay here. The Inn at Penn is a great fit if you want a quieter University City base, especially if you have business around Penn or just want a more campus-centered stay.
For this trip, it worked well for me. After checking in, I crashed. I turned on The Office, which has basically become my favorite hotel comfort show, and I was knocked out.
A Rainy Saturday Detour to Wilmington, Delaware
The next morning, I woke up and decided to take advantage of how close I was to Delaware.
Wilmington is not far from Philadelphia, and since I had never been to Delaware before, I figured I might as well turn the trip into a two-state weekend. That is one of the best parts of traveling in the Northeast. States are much closer together than they are in Texas or out West, so you can sometimes check off more than one place without making the trip feel impossible.
I drove down to Wilmington and headed to Big Fish Grill on the Riverfront, a restaurant I had already heard about several times in the short amount of time I had been in the area. It had also come up in my Google searches for restaurants near Philadelphia and Wilmington, and even my Uber driver on the way there acted like I had made the right choice. He was right.
I was seated quickly and started with some kind of dip served with saltine crackers. I still do not know exactly what that dip was, but whatever it was, it was delicious. For my main meal, I ordered the crab cakes and fries, and that ended up being an amazing choice.
The food was great, but the setting helped too. Big Fish Grill sits along the Wilmington Riverfront, and even on a rainy weekend, the views of the Christina River gave the meal a nice sense of place. After lunch, I walked around the riverfront, took in the views, and stopped into Riverfront Market for coffee before heading back toward Philadelphia
Wilmington was not the main point of the trip, but I am glad I made the detour. It gave me a chance to check off Delaware, eat a great meal, and see a small piece of a city I probably would not have visited on its own right away.
Back to Philadelphia for the Liberty Bell and Independence Hall
After Wilmington, I headed back to Philadelphia for the historic part of the trip.
First up was the Liberty Bell. I was expecting a long line, but for my April weekend visit, it was not bad at all. That was a relief because I had heard from others that the lines can get much longer during peak summer travel, especially around the Fourth of July.
Seeing the Liberty Bell in person is one of those things that feels almost required if you are visiting Philadelphia for the first time. It is not necessarily something that takes hours, but it is absolutely worth doing. The bell has become one of the country’s most famous symbols of liberty, and seeing it in the city where so much of America’s founding history happened made the stop feel meaningful.
After that, I went over to Independence Hall for my National Park Service ranger-led tour.
This was the highlight of the Philadelphia part of the trip.
Independence Hall is one of the most important historic buildings in the country. It is where the Declaration of Independence and the U.S. Constitution were debated and signed, and standing inside a place that central to American history felt especially important with the country approaching its 250th birthday.
The ranger tour was great. It gave the building context and made the experience feel more alive than just walking through a historic site on your own. For any first-time visit to Philadelphia, I would say the Liberty Bell and Independence Hall are must-dos.
Even if you are only in the city for a short weekend, make time for them.
What Surprised Me About Philadelphia
Philadelphia was not exactly what I expected.
I thought it might feel like a more manageable East Coast city compared to New York, and in some ways, it probably is. But it still felt fast, older, grittier, and less relaxed than I expected. The people were not as outwardly friendly as what I experienced in places like Atlanta, Denver, Tucson, or even some of the other cities I have visited recently.
That does not mean people were rude everywhere or that the trip was bad. It just felt different.
Traveling across the country has made me realize how much regional culture matters. Cities do not just look different. They move differently. They talk differently. They treat strangers differently. They carry different energy.
Philadelphia had history, food, density, and importance. But it also reminded me that I personally connect more with the West and especially the Southwest. I like the slower pace, the outdoor access, the desert scenery, the mountains, and the way those places give me room to breathe.
That realization may have been one of the biggest takeaways from the trip.
What I’d Recommend for a Rainy Weekend in Philadelphia
If you are visiting Philadelphia on a rainy weekend, I would build the trip around history, food, and a comfortable hotel.
The Liberty Bell and Independence Hall are absolutely worth doing, especially for a first visit. The Liberty Bell is free and does not require tickets, but you still have to go through security. For Independence Hall, check the ticket situation ahead of time because tours can require timed tickets depending on the season
I would also think carefully about where you stay. The Inn at Penn was a strong hotel stay for me because I like Hilton properties, I wanted to try it, and I did not mind being based in University City. But if your main goal is walking to the historic sites, Old City or Center City would probably be more convenient.
And if you have time, consider a quick Delaware side trip. Wilmington was easy to reach, Big Fish Grill was excellent, and the Riverfront was a nice change of pace from rainy Philadelphia.
Final Thoughts
Philadelphia was not my easiest trip, and it was not exactly what I expected. The rainy weather, late arrival, rough airport experience, and faster East Coast energy made the first impression tough.
But I am still glad I went.
The trip gave me a chance to start checking off more of the East Coast, visit one of the most important historic cities in America, see the Liberty Bell, tour Independence Hall, stay at The Inn at Penn, and make a spontaneous Delaware detour for some excellent crab cakes along the Wilmington Riverfront.
That is the thing about travel. Not every city has to become your favorite for the trip to be worth it. Sometimes a place teaches you what you like, what you do not like, and what kind of traveler you are becoming.
Philadelphia reminded me that I love history, but it also confirmed that I am drawn more and more to places with outdoor access, slower moments, and landscapes that let me breathe.
Would I go back to Philadelphia? Yes, I would. I think the city deserves another visit with better weather, more time, and maybe a stay closer to the historic core.
But even on a rainy weekend, Philadelphia still gave me a trip worth writing about.
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24/50 States Complete! 🇺🇸
Dallas to Philly! You’re hitting the World Cup cities!
I’ve been thinking a lot about regional differences, too. Each state (and city) has its own personality.