How to Spend 48 Hours Eating Everything in Philadelphia

What’s the first thing that comes to mind when you think of Philadelphia?

The Fresh Prince of Bel-Air being born and raised in West Philadelphia?

Nick Foles, backup QB for the Eagles, running the trick play forever enshrined as the “Philly Special” against the Patriots in Super Bowl LII?

Independence Hall, the birthplace of the Declaration of Independence and the Constitution, and thus American democracy as we know it today?

For me, it’s a Philly cheesesteak. 

And for too long, this notion has only ever been a hypothetical, mostly morphed by pop culture (although isn’t everything?)

It was long overdue for me to finally venture up north to the City of Brotherly Love and put my money (and their food) where my mouth is.

Friday

The entire weekend was marked in advance by the approach of a nor’easter, one of the funnier weather pattern names. Luckily, my morning flight arrived with no issues or delays, but as soon as I looked out the window when we landed, I could see the snow had arrived as well. 

As my Lyft slowly traversed the highway en route to my fraternity brother Matt and his fiancée Cam’s townhouse in Queen Village, I took in the city.  The distant skyline had a metropolitan appearance, but everything in my immediate foreground appeared more industrial. As we passed all three major league stadiums, grouped in a tight cluster, I hoped to catch a glimpse at the statues at Lincoln Financial Field (home of the Philadelphia Eagles) of former Head Coach Doug Pederson and Super Bowl MVP Nick Foles, neither of whom is still on the team, but they were unfortunately obscured.

After arriving and dropping off my bags, Matt and I knew we needed to tear the Band Aid off and get what was necessary to be a true Philly tourist: a Philly cheesesteak.

Philly Cheesesteaks

We went to a bar called Milk Boy and ordered our sandwiches to be brought from across the street at Jim’s South Street. I got mine with onions, hot peppers, and…provolone. I know, I know, it’s not authentic without Cheez Whiz, but I’m just not big on processed cheese sauce.

The sandwich itself wasn’t my favorite (though the peppers added a great spice and flavor and the side of fries were crispy and absolutely divine), but I’m glad I could check it off my bucket list and move onto the second item on the list: visiting Independence Hall and the Liberty Bell.

Independence Hall and Liberty Bell

Nothing fires me up more than American history, so I always work it into a trip to a new city (and food, obviously). Independence Hall has always been high up on my list because so many of our nation’s most formative moments occurred underneath its roof, including the signing of the Declaration of Independence and the genesis of the Constitution. There’s a spine-tingling romance to stand in the same room where such foundational moments have occurred. 

Because the tour is only offered every 30 minutes, we had to wait outside in line for that entire duration.

(HISTORY JOKE INCOMING) We considered this an Intolerable Act worse than the Quartering Act. (HISTORY JOKE COMPLETE. CARRY ON.)

Looking around the Chestnut Hill area is a treat, with lots of preserved architecture (less than 300 years old, but still!) and no shortage of buildings to imagine Benjamin Franklin getting drunk in. Once our tour moved in, we basked in the original woodwork and light blue paint (who knew the Founding Fathers had such an eclectic aesthetic?) before making our way into the convention room where the iconic moments transpired.

It was here where I noticed the Rising Sun Chair, named for the engraving of a sun on the back, where George Washington sat while he oversaw the entire Constitutional Convention. Benjamin Franklin spent much of the convention pondering the design before making a beautiful connection to the newborn nation:

“I have often looked at that picture behind the president without being able to tell whether it was rising or setting. But now at length I have the happiness to know that it is a rising and not a setting sun.”

Like I said, there’s something awfully romantic about it all.

We followed this up by visiting the Liberty Bell (famous primarily for being a bad bell that broke) and then grabbing a drink at Paddy’s Pub, the inspiration for the main setting in It’s Always Sunny in Philadelphia. True to the show’s energy, we were yelled at by the bartender and left reeking of cigarettes, thanks to every other patron ripping indoor heaters like it was 1940. Is this just how people used to always smell?

At this point, it was becoming clear that the heaviest of the snow would be approaching as it became nighttime so we bundled up in coats and prepared our alcohol blankets before venturing to our nighttime activities, centered around an Italian feast.

Ralph’s

Ralph’s is the oldest Italian restaurant in America, founded in 1900; legend has it that Teddy Roosevelt grabbed a meal there on his way to the 1900 Republican National Convention! Today it’s run by the fifth generation of that same Italian family who first opened it. It’s practically a Philadelphia rite of passage, visited by the likes of Frank Sinatra, Joe Biden, and Taylor Swift. 

Matt, Cam, and I went full family style (is there any other option when you’re eating Italian? If there is, I’m not interested.) and ordered an array of side-sticking Italian grub.

We started with a roasted pepper and mozzarella salad, served cold and bursting with sweet flavor. 

Then we ordered their “Best of Philly” meatballs, which were simple and delicious. The side of burrata was a great contrast, bringing a mild creaminess to the mix.

For our main course, we got chicken parmigiana (a non-negotiable) as well as a side of gnocchi with vodka sauce and cavatelli with gorgonzola cream sauce. 

It’s a rare treat when you’re eating a meal and you just tune out from any conscious thought, tapping into your primal instincts to guide your fork to the right plate in the right order. Everything was phenomenal, and I only wish we could’ve ordered one of everything.

Although we had already eaten far more than we had any business doing, we still saved room for one cannolo, which was the perfect sendoff for this magnificent meal.

After eating at Ralph’s, there were two things I fully believed:

1. This was some of the finest Italian food I’ve ever had in my life
2. A mafia hit has been carried out here at some point

Riding the high of this meal, we went to a few spots to have a few after dinner cocktails. We saw a jazz band play at Bob and Barbara’s Lounge, home of “The Special”, consisting of a shot of Jim Beam and a can of PBR (this place was riddled from floor to ceiling with PBR merch and artwork ranging in all styles and eras). 

We went to Sonny’s and then 12 Steps Down to close out our night. Around the time we first walked to Ralph’s, there were light snow flurries. As we began walking home at the end of our night, we were entering the peak hours of the incoming snowstorm.

It was time to enter a brief hibernation and see what awaited us in the morning.

Saturday

I awoke to find the streets of Philadelphia covered in several inches of snow (and this isn’t even a snow-naive Georgia boy’s inflated guess…the meteorologists said so too!) Luckily, Philly handles snow far more aptly than Atlanta, so we encountered very few obstacles to our day, besides the cold itself. 

After finally mustering up the appetites to eat once again, we bundled up and trekked through ankle-deep and sideways-falling snow to get our first meal of the day. The things we do for a breakfast sandwich.

Anthony’s Italian Coffee & Chocolate House

Take one step into Anthony’s and you’ll be ready to hop onto your Vespa and explore the Sicilian countryside en route to the mercato.

Every square inch of this place is bona fide Italian. The speakers were blasting romantic Italian ballads as well as opera. Even if you don’t speak a single syllable of Italian, you’ll feel like you belong. An additional signal of their authenticity is, of all things, the pluralization on the menu. They use the proper singular “panino”, rather than “panini”, which refers to multiple sandwiches. You’d order one panino or two panini. Grammar is cool no matter the language!

I opted for just one panino this morning and as soon as I saw the House Special, or the Gavone, my mind was made up. The Gavone is a pressed croissant sandwich with prosciutto, sweet peppers, bacon, sautéed spinach, egg, and cheese. It was a delectable sandwich, both rich and light, and it paired phenomenally with my energizing and freshly brewed Americano.

After our frigid foray through the flurries to and from Anthony’s, we took it easy for the afternoon before our evening plans. 

We made a quick trip down the street to grab a couple slices of pizza from a neighborhood spot called Little Italy, where the self-proclaimed “pizza freak” owner served us right before closing up to get out of the snow. I had an absolutely average slice of sausage and of Buffalo chicken with a house salad that was the complete stereotype of a pizza place’s house salad (a full jar of olives, three huge slices of tomato, a few bell pepper slices, and a cup of watery vinaigrette).

It wasn’t up to par with the rest of that day’s eating, but sometimes you just need a hot slice on a snowy day.

As afternoon turned to evening and the snow stopped falling, the PM part of our Saturday was kicking off.  

We grabbed a quick drink at a hole-in-the-wall spot in Center City called Dirty Frank’s where there was allegedly an urn of a former patron’s ashes in a literal hole in the wall. Then, we ventured a few blocks down to the Merriam Theater at the Kimmel Center to see Tig Notaro perform her dry brand of stand up comedy and bring the house down.

After the show, it was suppertime.

Sampan

Sampan in Midtown Village serves modern Asian cuisine. With a dramatic mural across the center wall, it’s one of the few places where the decor looks as good as the food tastes.

Our group once again opted for the tried and true approach of “ordering a whole lotta stuff and eating a little bit of everything”. We ordered close to a dozen dishes and each one was ridiculously good.

We started with the impossibly tender and tasty Korean BBQ beef short rib topped with crunchy kimchi. 

Then came the fantastically crispy spring rolls, filled with chicken, shrimp, and cabbage as well as the order of their exceptional edamame dumplings, which contained a mushy paste of edamame and truffle and was served in a sake broth. 

Next it was dumpling time. We got General Tso dumplings and an absolute Philly statement dish: cheesesteak bao, topped with a sour and spicy cherry pepper relish. It was as weird (in the best way) as it sounds.

For our main course, we got the Szechuan chicken stir-fry with sides of spicy brussels sprouts with puffed rice and fish sauce as well as the kimchi fried rice with shrimp, shallots, and a poached egg.

Every single course elicited an aggressive exclamation from everybody at the table, ranging from moans to expletives (or a strange combination of the two). Asian cuisine combines different flavor profiles better than any other: every dish is teeming with salty and spicy and sweet and bitter and the ever-elusive umami. 

The food fully satisfied and the accompanying cocktails were bold but never excessive.

Still feeling light on our feet despite gorging ourselves, we went to several other bars afterward. We ran the gamut of bars, from the oddly erotic artwork in Franky Bradley’s (while a montage of Arnold Schwarzegger’s Japanese commercials played on the TV screens) to the college bar feel of JJ Bootleggers (where I embraced my inner college kid and ordered several vodka-Red Bulls).

As fun as the night had been so far, there was still one item left on my Philly to-do list. If I flew back to Atlanta without factoring it into my itinerary, I would have only considered my trip a partial success. I had to venture to the Promised Land, but rather than the Land of Milk and Honey, it’s the Land of Gatorade and Cigarillos.

It was time for Wawa.

Wawa

Does any name command greater respect among Philadelphians? 

I’ve met dogs named after this iconic chain, heard stories of wedding proposals on its tile floors, but above all, I’ve heard praise for its lionized late night subs.

No two syllables have ever carried such weight among the inebriated and the hungry in Philly and beyond. 

Wa. Wa.

My guide Matt was a whiz at the order kiosk, zipping through building my sub, helping me make sense of the scriptures of Wawa. I got a turkey sub with garlic aioli, pepper relish, provolone, and a side salad’s worth of veggies on top with a bag of Voodoo chips and a hodgepodge of other prepackaged snacks. When the employee ringing us up found out I was a first timer, she went around to the back to tell the sub team to make it extra special.

Maybe it was the alcohol, maybe it was the appreciation for the brand, maybe it was the timing, or maybe it was the 13-degree temperatures…but that first bite of my sub was one for the ages

My initial takeaway was that this is pretty much Philly’s version of In-n-Out to Cali folks, or Pub Subs to Floridians…a regionally beloved chain that is indeed very good but ultimately unexceptional. It still does exactly what it needs to do. 

A Wawa sub might encapsulate Philly better than a Philly cheesesteak despite the latter boasting the city’s name.

After blissfully eating the first half of my sub and the miscellaneous snacks, it was bedtime.

Sunday

There are certain athletic performances of resilience and endurance that have deservedly gone down in history. 

Michael Jordan’s flu game in Game 5 of the 1997 NBA Finals, Braves pitcher Charlie Morton throwing 16 pitches on a broken leg during the 2021 World Series, and Terrell Owens netting 122 receiving yards in Super Bowl XXXIX on a broken leg.

Us eating anything at all on Day 3 of the trip should be entered into that conversation. Especially once you see what the Famous Fourth Street Deli had to offer. 

Famous Fourth Street Deli

You don’t call yourself “famous” unless you have the credentials to back it up. 

This deli has been doing just that since 1923. 

The decor has everything you’d hope for in a kosher delicatessen: photos of old New Yorkers, posters for local plays and Broadway shows, and plenty of Yiddish mantras. I felt like I was at my Nana’s for Rosh Hashanah!

Our waiter clearly knew his stuff and served as my personal guide as he held my hand throughout the ordering process (metaphorically, but might as well have been literal).

His wisdom was needed and appreciated, as we were ready to absolutely go to town on our order and rattled off a laundry list of items.

Everything arrived in ridiculously large portions and with oodles of flavor. 

The matzo ball soup contained a matzo ball quite literally the size of a dodgeball. The soup itself was a little busy with the chicken and pasta, but the matzo ball was rightfully the star of the show, with a fabulous schmaltzy taste and a dense bite that was right on the money.

Then, out came a platter of potato pancakes made with a 50:50 blend of potatoes and love. Even the accompanying applesauce was a treat.

For my main course, I got a pastrami and swiss omelet with home fries and a toasted everything bagel. I don’t exaggerate in the slightest when I say that the omelet was bigger than the plate. 

There are three things you should know about how Jews eat. 

1. We order too much.
2. We eat until we’re uncomfortable.
3. There’s always room for dessert.

We had no choice but to order a black and white cookie, assuming it’d be a nice light treat to cap off a lovely brunch.

How naive we were.

It was less a black and white cookie and more a black and white cake, taking up the entire plate. We hardly made a dent in it, or anything else on our table for that matter.

The Jewish tradition of ordering way too much food was alive and well in the Famous 4th Street Deli. With servings this large, they clearly have experience with customers needing leftovers because even the to-go boxes and bags were convenient. The boxes sealed shut easily and securely and the bag was so large I could have used it as a carry-on for my flight that afternoon, with room to spare.

Departing

After allowing myself some time to digest, it was finally time to head to the airport and return down south.

I stuffed my luggage with an absurd amount of leftovers: most of my pastrami omelet, a latke, half a bagel, four deli cookies, and the other half of my Wawa sandwich, prompting a very confused look from the TSA agent scanning my bag.

At the end of my journey, as I sat in my apartment nursing my knees, sore from a weekend of trudging through the snow and then sitting on a cramped flight, I devoured the other half of my Wawa sub, perfectly soggy from the aioli and relish, and munched on a leftover cookie. 

I’m not sure what six hours of sitting in a backpack does to a sub, but I wouldn’t have changed a thing about it.