5×5: Pittsburgh

Take note: here are five of the best local secrets from the City of Bridges…

The ‘Burgh – home to Andy Warhol, Primanti’s sandwiches, and over 400 bridges, Pittsburgh is an eclectic little city that sits on the corner of three mighty rivers. I reached out to five Free People store employees to give me a quick look inside the best their city has to offer. Welcome to 5×5: A series where 5 locals offer up one of their must-see, must-visit, or must-do sights. Get a glimpse into Pittsburgh by checking out the recs below and start planning your itinerary now!

Cara Berrigan: Assistant Store Manager

The City Skyline
Made nationally known by the Perks of Being a Wallflower adaptation, one of the Burgh’s best-kept secrets is actually a fairly obvious one: the incredible view of the city skyline.  From the time you enter the city through the Squirrel Hill tunnel, make sure you have your camera ready for the incredible views as the skyline opens up right in front of you. With more bridges than anywhere in the world, the city provides a grand entrance and unique views from every angle. Looking for the best spot to get an Insta-worthy snap? Atop Mount Washington at night you will find incredible views of the city that sits on the three rivers. It seems like a fairly obvious aspect, but one that can too easily be overlooked by “yinzers” and travelers alike.  So next time you visit the ‘Burgh, make sure to stop anywhere, and simply admire. 

Angela Battistone: Full Time MIT

Grist House – 10 Sherman St, Pittsburgh, PA 15209
This craft brewery is easily my favorite little treehouse in the city. The vibe here is unbeatable – flurries of string lights, an old barn wood bar, and a cozy beer garden full of pups (did I mention they’re dog-friendly?!). Each day they wheel in different Pittsburgh food trucks and immediately fill the space with gyros and cheesesteaks. But when the mac ‘n’ cheese truck comes… then it’s game over.

Jen Nyce: Assistant Store Manager

Pittsburgh Opera — 237 7th St Pittsburgh, PA 15222
If you’re looking for big culture in this (somewhat) small city, look no further than the Cultural District downtown! Namely, the Pittsburgh Opera at the Benedum Center. If you’ve never been to an opera before, the Benedum makes for a gorgeous introduction. As the premier opera company in Pittsburgh, you’re likely to witness the talents of those who’ve performed on stages such as the Metropolitan Opera, but for a much more affordable ticket. The shows are always changing from season to season, so put on your most appropriate night-at-the-opera outfit and head out to see the Marriage of Figaro next! And don’t worry, there are English subtitles.

Justina Honsberger: Assistant Visual Manager

Commonplace Coffeehouse in the Mexican War Streets – 1501 Buena Vista St, Pittsburgh, PA 15212
Tucked back on a quiet street in a historic and beautiful neighborhood of Pittsburgh’s Northside is this tiny coffee shop, lovingly operated by a local family and always buzzing with peaceful energy. The space is bright, intimate, and decorated with a rotating assortment of local art (which I love to shop for my home and gifts), and I’m certainly not the only one who finds it such a cozy and inviting place to spend a weekday morning! Stop in on a Monday around 10am and you’ll find every seat occupied, but if you stay for a minute a seat will open up at one of the larger communal tables in the window. The coffee is locally roasted about an hour outside of the city and expertly prepared (my personal pick is a honey lavender latte made with oat milk). Grab one of the baked donuts to go along with it and feel the magic begin. It’s the perfect way to kick off your day!

Angie Chilcott: Assistant Visual Manager

Jerry’s Records – 2136 Murray Ave, Pittsburgh, PA 15217
Even if you don’t collect records, you need to find your way in to this historic piece of Pittsburgh. (And if you do, you’ve found a goldmine!) The shop is quite literally covered from top to bottom in vinyl of all genres. Jerry Weber, who opened his namesake over 40 years ago, touts his shop as home to the largest collection of fine vinyl at the most affordable prices, with almost half of the store under $10. He always has a story to share, too!

There you have it, five Pittsburgh hot spots straight from the locals who know. With so much more to be discovered in the Steel City, be sure to stop by our Pittsburgh Free People stores and say hello to the locals above!!

+ Have Pittsburgh secrets to add? Let us know in the comments below!

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6 years ago

Great pics! :)

6 years ago

Well done Taylor!

6 years ago

Looks amazing, would love to visit Pittsburgh!



6 years ago

It’s the Ft Pitt tunnel . . .

Yinzer in NYC
6 years ago

I’ll definitely try these spots when I get back home but I have a few additions. Pittsburgh is in the spotlight right now as an up-and-coming city and has a lot to offer.
1. The food scene in Pittsburgh has especially been in the public eye. Restaurants such as butcher and the rye and meat&potatoes are popular spots for locals.
2. The strip district is one of my favorites. A strip of food markets, restaurants, vendors etc. True Pittsburgh culture can be found here.
3. Art: Andy Warhol museum, The Mattress Factory and Randyland for a psychedelic public art experience.
4. Other great spots: arsenal cider house, bop around the old historic town of Lawrenceville (aka the Brooklyn of Pittsburgh).

Lastly but not least, Pittsburgh is the city of champions. Attending a sporting event is an experience in and of itself. Pittsburgh is a city full of passionate people who bleed black and gold all year round


I have to find time to visit Pittsburgh one day!

Charmaine Ng | Architecture & Lifestyle Blog

6 years ago

@Maria above: she obviously meant that the Fort Pitt Tunnel scene in the movie helped to make the skyline famous, not that the Squirrel Hill Tunnel was. If she had, I’m sure the sentence would’ve read “made famous by the movie, the Squirrel Hill Tunnell allows you incredible views, etc.” She clearly wasn’t saying that the Squirrel Hill Tunnel was the exact tunnel from the movie…
Loved this post! So happy to see the 5×5 is making a comeback here on the blog!