Not one week after returning from a six-day, 3111-mile road trip, we spent Saturday thru Monday of Memorial Day Weekend on another thousand-mile journey, essentially to buy a shirt!
Our youngest enters college this fall and only made her enrollment decision after we had already visited the school. She wanted some branded shirts to wear for her final weeks of high school to show off her college. We were scheduled to be in Pennsylvania for a family event anyway, and her college is in the neighboring state of Ohio. Why not extend the trip to get the shirts?
More comfort food and sweets
Just as we had done on our road trip to Fargo North Dakota, our road trip to Pittsburgh, with a day trip into Gambier, Ohio, gave us ample opportunity to indulge our love for comfort food and sweets. Our first stop, for lunch with family in Pennsylvania, was BJ’s Brewhouse, a multi-location restaurant that we have also been to in Jacksonville.
We go there for the Pizzookie, which as the name implies is a cookie dessert served in a deep dish pizza pan so it emerges like a sweet pizza. This time, we had the triple chocolate, which is a double chocolate cookie with chocolate ice cream. in the past, we’ve also had the peanut butter, chocolate chunk, and cookies and cream varieties, which are just as good.
For dinner on our first day, we went to Eat’n Park, another multi-location restaurant we frequent when we’re in Western PA. This is a restaurant whose brand centers around smiley face cookies. Coincidentally, that same daughter bought a shirt here in the past – Keep Calm and Smile! We go to Eat’n Park for the pie desserts. This time, we had a slice of peach, warm with vanilla ice cream.
On our second day, after our side trip to Gambier for the shirts, we stopped at Jake’s Steakhouse, where we had more delicious comfort food – nachos, boneless teriyaki chicken wings, pulled pork sandwich, and chicken over pasta. It’s a great place to know about since it’s close to the college, so we’ll be back.
For dessert, we went to Whit’s Frozen Custard, founded in Ohio, but a place we actually discovered in Jacksonville. Frozen custard is like a very creamy, soft ice cream. Whit’s rotates the flavor of the day. Otherwise, you can get vanilla with various mix-ins that essentially create a range of flavors for you. Scott opted for the flavor of that day – chocolate peanut butter. I picked the Grasshopper, which is the vanilla base with mint sauce and chocolate flakes. I ordered a Small, which was way too big. Apparently, the Mini would have been the right size.
On our third day, we stopped at another one of our road trip staples, Dutch Pantry, on our way home. We had just stopped there on our Fargo road trip the week before, but we wanted our daughter to have a taste. This time, we saved room for our favorite dessert, the apple fritters, which taste as good as they look.
An expansive view of downtown Pittsburgh
I’m sure our daughter would say the highlight of the trip was finally getting her college shirts. But for us, it was visiting the Duquesne Incline area to see a panoramic view of downtown Pittsburgh. We rode the Incline in a previous visit, so opted not to do it again. It’s $5 per round trip and a very short ride. You can get the view from an overlook attached to the Incline terminal, and there is no charge to enter the terminal. The terminal also has historical articles and memorabilia about the Incline and Pittsburgh overall.
We loved the imposing statue of George Washington and Indian scout and Seneca leader Guyasuta, who evidently met in the area in October 1770. The spot overlooks the three rivers and the city of Pittsburgh, and is located just a bit to the northwest from the Duquesne Incline, in a place aptly named Point Of View Park.
Another money-saving tip is to access the terminal from the top, not the bottom. We arrived at the bottom of the Incline, and it would have been $10 to park in the lot. Instead, we found free street parking on the upper level (it was a holiday), and we were able to enjoy the view without having to pay to ride the Incline.
Photo with the founder of Randyland, a top 10 museum in Pittsburgh
After the Duquesne Incline, we visited Randyland, a townhouse turned art museum, where all the objects on display are reclaimed and recycled. The founder, Randy Gilson, was greeting visitors and posed for pictures with us. He’s expert in taking selfies!
The art pieces are in the yard next to the townhouse. There is a wall of welcome signs from around the world, including the Philippines and Costa Rica. The museum is free, with donations of course accepted.
My favorite piece was a sign from the New Orleans Police Department.
Visit to Bicycle Heaven, the top-rated museum in Pittsburgh
We also visited Bicycle Heaven, ranked #1 in TripAdvisor for museums. This is another free museum, again with donations accepted.
This multi-level and multi-purpose venue houses a museum with collectible toys and other memorabilia, space for selling, renting and repairing bikes, and even a nail salon. It’s a tight squeeze, and my daughter and I were overwhelmed by the vast array of objects, cramming every spare inch of space.
We stayed downstairs, while Scott ventured upstairs to see their huge space with tons of bicycles and other collectible items, some famous!
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We love Pittsburgh, an artsy city with a busy downtown adjacent to no less than three rivers. We are excited to visit more regularly in the next four years, as our youngest will attend school in Ohio.
For our Pittsburgh-based readers, any recommendations?
We are Scott and Caroline, 50-somethings who spent the first 20+ years of our adult lives in New York City, working traditional careers and raising 2 kids. We left full-time work in our mid-40’s for location-independent, part-time consulting projects and real estate investing, in order to create a more flexible and travel-centric lifestyle. 
Financial independence and early retirement is not something we originally focused on, but over time realized it was possible. Our free report, 
Wow, sounds like you favor desserts — not that there’s ANYTHING wrong with that. In fact, I think it’s a sign you’re living right. You made me want soft-serve frozen custard. There’s Culvers here, but it’s not soft serve. Still, it may have to do.
Sounds like you had a blast in Pittsburgh, which is great. And I love that the road trip was sparked by the desire for some shirts!
I’ve heard of Culvers but have never had it. I will have to check that out — always interested in desserts:)