Philly's Trendiest Street Fair Doesn't Hold A Candle To Its Working Class neighbour

Mandi Woodruff

When I rolled into Philly last Friday, I only had one end goal in mind:  

To prove that this town has more going for it than cheesesteaks and Ben Franklin impersonators, and to do it with less than a hundred bucks.

Since it was May (i.e.: high outdoor market season), I decided to hit up two of the city’s iconic –– and wildly different –– street festivals: The historic Italian Market Festival and the über-trendy Rittenhouse Square Row Festival. 

The two are held only 20 or so blocks apart, but the differences couldn’t have been any more stark. 

First, let's set the scene. The festivals are just over a mile apart, with the Italian Market Festival (A) further South and Rittenhouse Square (B) closer to downtown.

They couldn't be more different. The Italian Market is the oldest outdoor market in the country, open 7 days a week, year-round, smack in the middle of Philly's historically Italian (and increasingly hipster) 'hoods, Bella Vista and East Passyunk.

On a normal day, Rittenhouse Square is a quiet residential area. It's been one of the more upscale areas in the city since the mid-19th century, when it was home to Philly's Victorian aristocracy.

I started my day at the Italian Market, where people were already chowing down and packing the streets by 11:30 a.m.

There were multi-generational families clustered everywhere.

Some kids chased bubbles ...

Others chowed down on perfectly greasy pizza and hoagies ...

And everyone else queued up to ogle this balloon artist.

City-favourite Isgro's was inundated with sweet-toothed customers vying for at taste of their famous cannolis.

Everything that was served up looked like it had come straight from your grandma's kitchen.

And there was a real emphasis on supporting local businesses along the festival route.

They could have doubled their prices for the festival, but everything I ate was cheap and incredibly tasty –– like this $10 sausage sandwich from Paesano's. It was more than enough for two.

The best part was being able to step into the physical restaurant, which was conveniently right along the festival's route.

I had to poke my head inside Philly's famous cheese shop, Di Brunos Brothers. Throngs of people packed the shop and it smelled as close to heaven as I've ever come.

Not to mention the fact that they were serving up some seriously cheap and delicious eats for less than $5 right outside.

A mile away, at the Rittenhouse Festival, it was pretty much like landing in an alternate universe.

The minute I ran into this fully-stocked wine shop, I knew I wasn't in Italy anymore.

The only pastries I saw were packed in cellophane and stored in cardboard boxes under the table.

And in lieu of cheesesteaks and sausage sammies, you could munch on a $6 crab cake slider.

And wash it down with a $6 green smoothie.

Not that any of that would fill you up, so go ahead and head on over for a mini taco –– $3.50 a pop.

Too adventurous? Never fear. Shake Shack was right around the corner.

Of course, there was always Ben & Jerry's –– which had the audacity to charge $5 for a cone.

But good luck trying to find a real cheesesteak. Mini Philly steaks and fajitas were about as close as you could come at the Rittenhouse festival.

But hey, people still seemed to dig them.

And if you wanted to cool your heels for a while, you could always pop into Urban Outfitters.

Or pick up a pair of $100 designer heels for a steal.

The Di Brunos Bros table wasn't getting anywhere near as much love as their brethren at the Italian Market.

Maybe because they tacked an extra $2 to $3 onto their sandwiches...

I wound up walking away with a $3 watermelon juice, feeling grateful that I'd filled up at the Italian Market beforehand.

The kiddies at Rittenhouse had plenty to keep them occupied.

Like these face painters ...

... who were hired by Capital One to market their kiddie savings accounts.

And Rittenhouse's resident balloon artist had a bit more going on than puppies and princess crowns ...

He was a big enough deal to get the local press's attention at least.

And a huge crowd of fans.

At the end of the day, I can't pretend I didn't have a better time (and save more cash) eating my way through the Italian Market festival.

After all, they did have a live band.

And this ... Rocky Impersonator.

Plus, where else could you pick up a beer bottle drinking glass?

Or do your grocery shopping ...

... while sipping a piña colada out of a giant pineapple?

There was just too much life, history and good ol' down home soul not to suck me in.

Now see how I fared on the ultimate Philly mission:

I found the best Philly cheesesteak in the last place I'd think possible >

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