A Tryst in the Strip
- grws269
- Feb 22
- 7 min read

On our second venture into Pittsburgh, our travel class paid a visit to some of Pittsburgh's most frequented attractions: the Strip District, a tour from Molly's Trolleys, and the Duquesne Incline.
Saturday, January 25th was a busy day in the Strip. I'd been there multiple times, once for a haircut falling accidentally on Saint Patrick's Day, then over the summer, usually on weekdays while I made a stop at one of the various markets or scoured the area for a bite to eat after wrapping up cat-sitting. (Long story!) While the 25th wasn't anything like St. Patty's, it was still bustling and active, with cars and people alike making for a human-on-metal maze. There also happened to be a large convention at a nearby center, likely a dance or cheer competition, which contributed to the thick weekend traffic.
As a result, we began with little time to mill about before our trolley tour-- but not too little to keep us from visiting some of the famous and upright historical shops that define the Strip. To these places I had never been.

Our first stop was at the Pennsylvania Macaroni Co. Despite my prior research on the place indicating it was primarily an Italian market, I somehow naively expected there to be more of a mac-and-cheese vibe. Thankfully, it was such a loaded shop, I had nothing to be disappointed about. The walls were lined with spices, grains, dried pasta, packaged candy and dehydrated fruit, olive oil, sauces, breads, and more; anything you could need to stock your pantry and whip up a hearty homemade meal. Not to mention the glorious deli counter!

Since its founding by the Sunseri family in 1904, Penn Mac has cultivated and retained the vitality of a business at the heart of its community. Individuals peeked around at every corner, perhaps looking to try something new, while others milled around with family and friends for a casual grocery trip. I was among the newbies, and I was especially interested in a small, self-serve olive oil taste-test station (in front of a MASSIVE selection of olive oil). You bet I tried it for myself. I believe I had the Masserie di Santeramo extra virgin olive oil; its flavor was smooth and light, with a slightly bitter finish. Oh look, now I sound pretentious. What I should say is that I liked it.

After Penn Mac was another Strip staple: Grandpa Joe's Candy Shop. This one is hard to miss from the outside, and yet stranger on the inside. Weirdly enough, I've been to more candy shops in Pittsburgh than I have anywhere else. And I used to live a few miles away from a Mars factory. Coincidence? I think not. There must be a nearby candy big-shot to blame...

With the business of daily life, not everyone had time to stop and chat about why they found themselves in Grandpa Joe's; however, one kind woman who couldn't talk went out of her way to grab the attention of someone who could: Ron, a friendly Pittsburgher local to Brighton Heights.

Ron and his family had just come from lunch The BeerHive, which he suggests ages 6+ for family trips and says has "great food and good atmosphere." More about that soon!
When asked his favorite place to visit in the Strip, Ron answered, "Wholey's" in a total Pittsburgh accent. It's not often I hear it clearly, but when I do, I hear it in vowels-- usually, 'o'. That's one of my favorite things about living in different parts of the country; people tend to tell me I have a midwestern accent, and, over time, I start to hear how other people's voices actually differ from mine. Wholey's is one famed place in the Strip I have yet to visit, so it's next in line for a solo trip. But my next stop that day was to The BeerHive to get a feel for some casual Pittsburgh drink and dining. Thanks, Ron, for a warm interview and two great recommendations.
After a return to the bracing January cold, The Beer Hive was a nice respite. Unfortunately, my status as both a semi-new legal drinker and a seasoned food service worker caused me to freeze as I tried to interview the bartender. What can I say? It was around 1:45, likely post-lunch rush, the bar itself was mostly full, and my want for talk was overridden by nervous over-politeness. So instead of asking her a question, I ordered a beer. (After I forgot what a Modelo was and had to settle for a Corona with lime, the only beer I could remember that wasn't a Bud Light.) I am fallible and a human and though I love interviewing, it can't always work out perfectly.
But Ron was right: the atmosphere was good, darkly-decorated but well-lit by tall street-facing windows, and despite my embarrassed fumble, the bartender was patient and gracious. I'll have to return to try the food.
Too soon after I ordered, it was time to book it to our class rendezvous point (wow! I spelled that right on the first try!), so I had to chug my Corona and power-walk to meet the trolley tour.

Our trolley tour was a two-hour excursion that took us straight through the Strip district and throughout the city, riding over Pittsburgh's telltale bridges and up to Mt. Washington, down again on the Duquesne Incline, and back to the Strip. Our tour guide, Don Mike (found here on Instagram), was incredibly funny and knowledgeable. He provided classic Pittsburgh trivia alongside the general tour, of which I knew little but learned a lot, though I did succeed a geography check in naming the Ohio River! I was proud of that one. If you're a fan of educational sightseeing, a Molly's Trolley tour is a must. The ride itself was comfortable, with intermittent heating and a clearly experienced driver. And I say that as someone who thoroughly despises Pittsburgh driving. Now, I won't spoil all of the details for you, but I will name a few of my favorite moments:

If you recognize the location above, you might know a peculiar bit of trivia that makes this park across from the Benedum Center for the Performing Arts so special and unique to Pittsburgh. As I said, no spoilers! But here's a hint: think about the time of year this photo was taken, and Pittsburgh's primary economic boon that gave the city its honorary name.

The Duquesne Incline was an enormous highlight on our tour, despite my fear of heights. According to their official website, this incline was opened in 1877 and restored again by local residents in 1963. The incline remains a form of public transit as well as a historical gem, featuring the David H. Miller Working Museum. What's more, our class was lucky enough to board the incline just after an actual wedding! First came out some of the wedding party, including an adorable flower girl, before the bride and groom emerged, smiling and holding hands. What a beautiful ceremony it was at a spectacular landmark.


One particularly Pittsburgh-esque fun fact Don Mike provided: on the nationally-loved T.V. series "Mister Rogers' Neighborhood" set in the Steel City, the trolley that takes viewers to the Neighborhood of Make Believe was once supposed to be an incline, but the infrastructure was so specific to Pittsburgh that producers believed a trolley would be more universally appreciated. I would argue that, in the spirit of my two writing professors Jakiela and Newman, the originality and specificity of the incline would have made it all the more engaging, not less. Alas, I can better appreciate the little red trolley and its heritage knowing what could have been.
Of course, many of the sights visible on the trolley tour were seen while moving and didn't make for the most picturesque photos from my vantage point. That's just the perk of taking such a tour; you go not to get a full experience of every monument and business, but to window-shop the city's history and present, taste-testing just a little cup of its many flavorful facets.
Speaking of flavorful, two of my fellow students and I made a final pit-stop at Bella Notte, a reasonably priced Italian eatery a short walk away from Wholey's. I enjoyed a vegetarian sandwich on some really delicious, soft focaccia bread, and we received kind and expedient service. Thanks to those at Bella Notte!
Though our time in the Strip itself was regretfully short, no single day trip could encompass all of the tempting food, shops, and third spaces that pack the streets. A few tips for the area: parking is hard to find, especially on a weekend. There is paid streetside parking with daily and hourly exceptions, as well as paid lots, including those that will park your car for you and keep your keys. Drive carefully in the city; as an out-of-towner, I loathe Pittsburgh driving in general, but the Strip streets can prove especially narrow and the turns especially blind during peak rush hours. Finally, expect foot traffic, and always J-walk with caution. Just kidding, don't J-walk. That's illegal.





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