Pittsburgh Road Trip 2017: Day 1 & 2

Pittsburgh Road Trip 2017: Day 1 & 2

Pittsburgh, PA

September 22-25, 2017


The city of Pittsburgh is like a real-life version of the board game Candy Land for my best friend Jess and I. The drinks are delicious, the food is appetizing and everyone we meet in our travels is sweet. All the places we experience give us a sugar high that makes us want to come back for more.

Our road trip to the 412 didn’t start off so tasteful though as the night before we were supposed to leave Jess got into a small car accident. Luckily she was fine, but her car wasn’t safe to drive from Canada to the Erie, PA Greyhound bus station.

We looked into a few alternatives such as renting a car or taking a bus from Buffalo, NY instead, but they were either too expensive or didn’t make sense with our travel timelines. Her boyfriend ended up driving us all the way to Erie at 4am and picked us up Monday night, which we were so grateful for since we had been looking forward to our long awaited girls weekend for months.


Day 1

We arrived in Erie, PA around 6:20am and Jess’s boyfriend dropped us off at Cracker Barrel so we could have breakfast before our bus ride. It was very quiet that time in the morning so our food arrived quickly. Mmm dem biscuits!

Cracker Barrel

It was a $24 USD taxi ride from there to the Erie Greyhound bus station, which I thought was cheap since it was about a 20-minute car ride away. We arrived early so we could check our luggage where the agent actually believed me when I told him my luggage was under the required 50-pound limit.

No one was running away with the weight of that suitcase let me tell you.  

The bus ride was comfortable reclining in black leather seats but seemed incredibly long at close to 4 hours. I think we drove through every hick town back road in PA before getting to downtown Pittsburgh. We were staying at the newly re-done Drury Plaza Hotel (used to be a Federal Reserve Bank) that was a 3-minute walk from the bus station.

We were given a room on the 1st floor, which we judged at first but it ended up being really convenient to maneuver our luggage and with bringing food/drinks back to the room. We had such a great view of the city though…


We dropped our luggage off and ventured out for lunch to a place Jess picked out called The Yard, which was located in Market Square a short walk away. They specialize in a variety of gourmet grilled cheese sandwiches and I loved my choice.

I ordered the Smack Yo Mama (yes I actually had to say that) and it consisted of BBQ pulled chicken, onion rings, beer/cheddar cheese on Texas toast. I didn’t really care for the tomato soup it came with as it kind of reminded me of pasta sauce and not so much soup.


Our hotel had some nice perks included: free breakfast every morning, free afternoon popcorn, a light meal each night, unlimited pop & coffee and a free alcoholic drink each night at the manager’s reception. An additional two drinks were available for purchase at $0.75 USD each. These were not weak drinks either. I recommend the margarita! We took these up to the 8th floor roof top patio to enjoy.


I’ve had this dress in my closet for the past 3 years waiting to finally wear it to Hyde Park Prime Steakhouse. Let’s be real- the fit wasn’t exactly the same as the purchase date, but I still loved the dress nonetheless.

We’ve wanted to eat dinner here every since watching ex-Pens player James Neal's episode of NHL 36. We made reservations for 7pm and took a cab over, as it’s located in the North Shore of the city.

All the carbs!

Jess ordered an heirloom salad and mac n’ cheese which I tried some of and both were amazing!

Hyde Park

Steak Crosby…yes that’s what it was called. Not gonna lie, I didn’t really care for the steak as it was very bland and boring. My boyfriend made a remark about how it’s just like Crosby’s personality. He’s clearly not a fan.

My meal came to around $73 USD which was expensive AF with them exchange rates, but we knew this going into it and told our wallets we were also paying for the experience. 

Getting a cab in this city is so difficult! It’s not like New York or Toronto where everywhere you look there is a cab waiting and willing to drive you around the city. Here you literally have to call a call centre and give your info, then another call centre will call you back to confirm this information, and then the cab driver will call you when their approaching. Come on Pittsburgh, we’re roaming here!

Once one finally arrived we went to Rivers Casino. This is basically a 10-minute walk away but it was around 9pm, dark, we were in dresses and heels, so we figured it was safer to take a cab.

We ordered the margarita @ The Wheelhouse, but they went downhill from previous times. We didn’t win any money, but enjoyed the view of watching Pittsburgh Pirates’ pitcher George Kontos on the big screen. Yaaa Pirates won!

Day 2

We pre-booked a hop on- hop off double decker bus tour of the city in advance through The Pittsburgh Tour Company. It was $63.50 USD for both of us and we thought it was well worth it as it brought us to all different parts of the city we wanted to explore. It consisted of 21 stops, which can be seen on this map. It’s approximately 1 hour and 15 minutes until another bus comes back around to continue the tour, so you have to make sure you plan accordingly or you will run out of time.

We got picked up at the Omni William Penn Hotel, which was just down the street from the Drury. They had all our information/wristbands ready for us when we boarded the bus, which was convenient. A worker wearing a microphone narrated the tour, so it was easy to hear things they were pointing out during it. 

Points of interest: 

  • Courthouse

  • Church with a 4 year wait list to get married in

  • Pamela’s Diner

  • Primanti Bros.

  • University of Pittsburgh then and now

  • Excuses Bar & Grill (I’ve previously ate here and the wings are different but delicious!)

We got off the tour at South Side Works and walked around there a bit. We found Hofbräuhaus, which we really wanted to eat at but ran out of time this trip.

We had perfect weather this entire weekend, which we were grateful for. Coming back home to Canada’s weather was disappointing to say the least.

Signed Sidney Crosby & Kris Letang jerseys at Shop412!

Shop 412

We got back on the bus and took it for one stop (seemed like forever when you are hungry) and got off to eat lunch at Fat Head’s Saloon. We picked this place because Jess’s family all call each other by the nickname "Fat Head" so we thought it was ironic. Unfortunately we were a bit disappointed in this place, but we also didn’t order one of their headwiches (sandwiches the size of a head) as we knew it would have been wasted with not being able to take it back to the hotel right away.

Instead we ordered a side salad each, split a basket of chips with jalapeño cheddar dipping sauce and the buffalo cauliflower. The salad and chips were good, but we both hated the cauliflower. It wasn’t breaded in anything or crispy pan fried- it was just boiled cauliflower with a sweet chili heat type sauce on them. It also took FOREVER for it to come out and we almost missed the tour bus we wanted to catch.


We stayed on the bus for about an hour where we toured further down East Carson street, past the Duquesne Incline, saw a view of Heinz Field across the water, past Rivers Casino, saw a glimpse of PNC Park and then headed over towards the Strip District.

Jess and I both love the Strip District! It has amazing deals on all things Pittsburgh and we find the best prices buying sports team merch here. They also have a bunch of coffee shops, markets and restaurants to eat at. We just made our bus in time again and headed back to our original pick up location around 5pm.

Strip District
Strip District
Strip District

As I wrote earlier, the Drury used to be the site of a Federal Reserve Bank. They have preserved the original vaults in the basement of the hotel, which are open for guests to see. They act as an entrance to the conference rooms.

I decided to switch up night two of the free drinks and went with a vodka cranberry. We got dressed up and headed to the South Side on East Carson Street for a night out.

I tried my first yuengling at Mario’s South Side Saloon and we also spun the shot wheel. We got honey and the reason I don’t drink brown liquor came back to me later in the night. Apparently Mario’s didn’t enjoy all the Avenged Sevenfold we played on the jukebox during our last visit there…

Jess’s “Iced Tea” and my Local Celebrity Rita @ Local Bar + Kitchen! This drink was the size of a small child and was so heavy it’s no wonder I don’t remember much of the night after consuming it. I woke up in the morning to a video on my phone of us belting out Shania Twain’s Man I Feel Like a Woman if that's any indication.

Even in my haze though I internally still knew to capture Crosby’s interview on TV.

The last stop of our night was at Diesel Club Lounge/ Skybar. Those end of night feels…


Click here to read more of the stuff we crammed into our girl's weekend on days 3 + 4. It basically consists of drinking more booze, consuming too many calories and baseball stalking Kontos.


Open Mic: 

1. What is your favourite hotel to stay in when visiting Pittsburgh?

2. Any restaurants we should check out next time we visit? (You know there will always be a next time for the 412) 

3. Are there are other good bar scenes in Pittsburgh other than the South Side? It's always so hard to find a cab to drive us back downtown where we usually stay. 

*Photos in this post are a combination of my own and from Jess.

Pittsburgh Road Trip 2017: Day 3 & 4

Pittsburgh Road Trip 2017: Day 3 & 4

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