Pittsburgh's Strip District Open Air Markets, Fine Dining & Nightlife

By day, the Strip District is a bustling network of sidewalk stores, boasting everything from Greek cheeses to local produce to Terrible Towels. By night, it transforms into a clubbing, bar hopping scene replete with upscale restaurants and fancy ladies in overpriced heels.

The Strip began as a shipping and industrial area along the Allegheny River immediately Northeast of Pittsburgh’s downtown. In the early part of the 20th Century, it was the heart of Pittsburgh’s economic endeavors. By the 1990s, it had become a mile and a half of mostly abandoned warehouses, home to rave parties galore and perhaps the residence of some of Pittsburgh’s more seedy goings on. Today, it’s been heavily gentrified and beautiful restaurants live next to trendy lofts.

In my college years, just around the turn of this century, I had fond memories of visiting an old record shop here in a time before mp3s had completely eliminated the idea of such an establishment for anyone short of novelty collectors. Lady pursued the last remnants of her raving days in these warehouses.

Later, when I lived in this fair city, the Strip was one of the primary examples of the renovation and renaissance in which the City of Bridges was engulfed. There have, as long as I’ve been around, always been street vendors pushing everything from greasy hotdogs to pierogies to souvenirs, even before the city could have ever been thought of as a vacation destination short of seeing a Steelers game, and it’s always been a spot for scantily clad ladies to get too drunk and coked up dudes to do their best to take advantage of such a scenario, but only in the past few years has the Strip really cleaned up its act and become a place where both uber-fashionistas and your mother could feel safe venturing out at night.

Try Eleven, just southwest of 12th Street, if you’re looking for a meal with humble roots but opulent decadence infused. A bar, plenty of interesting seating, from booths to cafe style loveseats, and a staff that knows how to treat someone about to drop $50 – $100 on a meal for two, depending on appetite and the number of drinks you order. Kaya is a similarly ravishing experience, seven blocks up Smallman Street.

For something cheaper and less flush, head to Primanti Brothers, Pittsburgh’s legendary sandwich shop (a local chain, actually, found in nearly every one of the city’s neighborhoods) featured on numerous Food Network type reality shows and known particularly for their sandwiches piled high with coleslaw and fries right there between your meats and your top slice of bread.

I personally love sipping a beer in the sun of Roland’s Seafood Grill & Iron Landing second story balcony, where you can watch the hectic action of the Strip go by from a safe, increasingly intoxicating level.

To try and pin down one restaurant that’s “the best” in the Strip is like trying to get a dart with no tip to stick into a cloud. Put on your baby blue throwback Penguin’s jersey and head down with the family during the day to pick up some produce, maybe a little halloumi, and a bag of pierogies made by someone other than Mrs. T. Then ditch the young ones later that night and tighten your tube tops while you dance the night away in one of a plethora of clubs where you can bump uglies with local drunks and stand in line for twenty minutes waiting for your next drink. Or skip the club all together and just walk the neon lights lit streets and amuse yourself with the stumbling antics of those younger, dumber and more beautiful than you drink their 20s away. Whatever floats your particular boat!