Mini Pittsburgh Trip

Over the thanksgiving break I was able to join my boyfriend on a surprise visit to Pittsburgh to see his mom.

^ (Bae & his mom)

Listen, he is so sweet. He bought his mom and aunt tickets to a Penguins game. He led them to believe he just bought the two of them tickets but secretly he bought 3 seats together in order to surprise them at the game. We arrived in town a little later than we’d like so they were already at the game when he arrived. He said when he walked up he exclaimed, “Hey! I think y’all are in my seats!” At first they were mad but then realized who it was & he described it to me like this, “I think they scared the whole section, they screamed so loud you would think someone was being murdered!” Haha! I wish I could have been there to see their reaction but I didn’t decide to join on this trip until after he purchase the tickets! 🙂

After surprising his mother and extended family we were able to join them the following day for Thanksgiving and then do some quick sight seeing the following {black} Friday.

We didn’t have too much time in the city but while were were there our tops picks were as follows:

1. Randyland

Randyland is a a modern day instagrammers dream. This is Randy’s home in which he has hand painted the most colorful pieces of artwork. His goal is to bring happiness to his neighborhood but he was able to bring a smile to this out-of-towners face with his artwork as well! Almost everything in his little section of the neighborhood is garbage that he repurposed! Love the artwork and his inclusive message. This is a must see spot!

2. The Andy Warhol Museum

This was Barkleys top pick! It’s seven floors of artwork either by Andy Warhol or inspired by. I knew Warhol’s most famous pop art but he created so much more than that. One thing I learned was he actually had long career in film.

^ This right here is Barkley watching a film of one of Warhol’s friends just smoking a cigar. Literally all it was. He said this was his favorite lol!

One of my favorites. I love bright colors and flowers and this is a combination of both!

I won’t put too many pictures of the museum because I think you should go experience it yourself! 🙂

3. Food!

Aside from eating a fantastic thanksgiving dinner at his mom’s we also ventured out to eat at some local spots.

Barkley had made us reservations at the Whitfield but when I woke up I was in need of a Belgium waffle stat! Lol so I went to yelp and found Waffles Incaffienated so we had to try it out. It was a neat little spot on “the south side” which is apparently where all the college kids hang out. They have all kinds of variations of waffles but I ultimately wanted something sweet and savory so I got the chicken and waffles and he got raspberry crepes. Would recommend if your in the mood for a good brunch! Only downside is no mimosas! 🙂

After our sightseeing were in the mood for Mexican so we stopped by Bakersfield downtown. This is a new age Mexican restaurant. We got street style tacos and pineapple margaritas! It was delicious and honestly not unreasonably priced!

Lastly, I will also recommend the room service at the Omni William Penn. I ordered a quesadilla from them late night and it was surprisingly one of the best quesadilla’s I’ve ever had! Who would have guessed?!

4. Lodging

Barkley booked us a stay at the Omni William Penn. I honestly had no idea where we were staying until like the day before we left! Lol I left the trip planning up to him and was not disappointed! This was a beautiful hotel!

There was a speakeasy on the bottom floor but unfortunately not open during our stay!

Their lobby was already decorated for Christmas so of course we had to get some pictures in front of their tree.

I chose my my actual thanksgiving outfit wisely! Knit poncho sweater (This one is a couple of years old but I have my eye on this one next!), wool hat (similar) , and leggings! I did not regret wearing my stretchy pants.

I made sure to dress super comfortable on our sight seeing day. I needed to be fashionable, comfortable, and warm and this sweater fit all 3! It’s longer and it’s so soft and warm! Currently going to buy it in more colors! And best part is it’s half off right now! Only $25!

I also brought an old vest (similar under 20$ rn!) that I bought when I worked at Loft back in college. This vest is such good quality and I’ve worn it for several winters already. You seriously cannot go wrong with LOFT vests they are very good quality! Currently eyeing more puffer vests like this!


These are seriously the most comfortable sneakers I’ve ever owned. If you need comfy walking shoes GET THESE!

Since we were going to Randyland I had to have my pop of color, too! Brought my trusty beanie.

I hope this helps ya out if you’re wondering where to go or what to eat if you ever make it to Pittsburgh!

Hope you all had a great thanksgiving!

Xo, holly

One thought on “Mini Pittsburgh Trip

  1. This is your mom. I love you to death and this is a great post. The surprise part made me cry a little. Just one thing, please remember your grammar rules. Thanksgiving is always capitalized when used as a proper noun! Keep writing! The blog is fantastic!


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