Cocktails + Eats Lifestyle Travel

36 Hours in Pittsburgh

November 2, 2017

We went back to Pittsburgh (first time in over a year) with Bear in tow to visit our sweet friends Jason & Tiffany and do a whirlwind exploration of the city. Tiff had recently relocated permanently  to the Steel City, and I wanted to redeem myself from my last visit where I (pregnantly) threw up in their bushes.

This time, we didn’t do the typical tourism that we did last time. This time, we pretended to be locals. Here’s a short guide of the places we went that had us feeling like we’d lived here forever.

The Strip District

A whole neighborhood that has street vendors and great restaurants, this area centered around Smallman St. could fill a whole day of exploration. There are places to buy fresh fruit and veggies, Steelers gear, amazing baked goods, sunglasses, etc. You name it, there’s a both for it on the street. Coupled with amazing restaurants and bars, and I am glad Jason & Tiffany live walking distance from here. IMG_4357

Smallman Galley

Located in the Strip District, this is almost like going to your dining hall in college but way better. There are two bars and 4 restaurant-style vendors that you go up to and order from. You can order a few things from different places, or copy us and everyone order something different. Except for Jason who ordered exactly what I did. There’s ample seating for everyone to sit together and enjoy brunch in the coolest setting.

Peace, Love, & Little Donuts

You guys know how much I love donuts. I’m addicted. Like, Krispy Kreme app on my phone in love. So when I found out there was a place in the Strip District that sold tiny donuts that I could have customized to however I’d like, I was in. The pricing is super affordable, and you can get so many donuts and share a bite with everyone to try them all. I went for a very flavorful variety, and was transfixed watching the donuts being made there in shop.

Point State Park

We went here in July 2016, but I still love it. A large park located on the water where the 3 rivers that run through Pittsburgh meet, this open space is always filled with cyclists, runners, kayakers, and people sprawled on the lawn or by the fountain enjoying the nice days. Bonus: you can see Heinz Stadium from here, so I bet the fireworks are phenomenal.


The Subway

Did you know Pittsburgh has a Light Rain system? With two lines connecting Downtown to more southern suburbs, you can actually get around a decent bit using the line. Bonus: Allegheny to First Avenue stations are fee free, so you can get around Downtown without having to walk or cab it. Here’s a map on the Port Authority’s site. If you want to visit Pittsburgh and explore downtown, but can’t find an AirBNB for an affordable place, this gives you the option to consider a place outside of the city but along public transit lines.


The Hotel Monaco Biergarten

Located on the 9th floor of the Kimpton Hotel Monaco in downtown PGH, the Biergarten offers German style biers, along with a small food menu. It’s an open air setting, giving you cool views of the city and allowing you to soak up sunshine and breezes while you play games they’ve got scattered around and enjoy a drink. I had the Frosecco (frozen prosecco mixed drink) and thought it was amazing. Also, Bear ended up in some groomsman wedding photos here so it’s obviously a great, family-friendly spot.

Condado Tacos

This is Jason’s favourite spot to eat in all of Pittsbugh, as noted by his frequent flyer card there. Now, I’m not a big Mexican food fan, but I actually really enjoyed this spot. You can build your own tacos (ideal for bland eaters like myself), or select from their Taco Suggestions menu. Pick one taco or five, share a big bowl of guac, and enjoy the Dia de los Muertos meets Street Art style on the walls.


As always, I leave Pittsburgh with the thought in the back of mind as “This is a city I could live in.” I love how walkable the city is, it’s proximity to recreation and bike trails, and how much public art there is. There is great street art in the neighborhoods, in the Light Rail stations, and even hidden coves along side streets.

Tell me, where are your favourite local spots in the Pittsburgh areas? Any recommendations for visiting with Tiny Humans/getting outside? I’m all ears!



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