Hidden Gems in Pittsburgh


As someone who’s done a fair share of traveling, seeing a city’s most iconic places is fun. But it quickly gets old with packs of tourists, long lines, and expensive ticket prices. For a recent trip to Pittsburgh, I thought I’d skip all of that and check out the best-hidden gems the city has to offer instead, and I wasn’t disappointed.

Places to See

Pittsburgh has a long history of love for cycling, dating back to the 1970s. This is why Bicycle Heaven is another must-see. This two-story warehouse and showroom is the largest bicycle museum/shop in the country, if not likely the world.


Bicycle Heaven is located right off the Three Rivers Heritage Trail. It has thousands of bikes and bike parts, many of them rare, and the friendly folks who work there are always happy to share niche bicycle knowledge about rare bikes. One such bike is the Bowden Spacelander, the first fiberglass bike ever created. Approximately 30 exist in the world, and this museum has 17 of them. The museum has bikes from the movies “Pee-Wee’s Big Escape,” “Fences” and “A Beautiful Mind.” Tours are free, but donations are welcome.

I didn’t find out until recently that Pittsburgh has one of the world’s major astronomical research institutions. The Allegheny Observatory is owned by the University of Pittsburgh, but between April and October, it offers free public tours Thursday nights. Unfortunately, my tour date fell on a typical evening. But there will be plenty of opportunities to reserve a spot during one of the evenings this year that the planets line up. I’m not mad about it, I was able to grab front row seat. The galaxy viewing was spectacular, and that kind of stillness is hard to forget.


My next stop was Randyland. The idea was to view the art of the city without being stuck in a museum all day and it didn’t disappoint. Randyland gets its name from its builder, Randy Gilson. About 20 years ago, Gilson used a credit card to buy an old, run-down building in the city’s North Side area. Over time he has turned it into a vibrant art space with murals, gardens and other incredible knick-knacks. Perfect for an afternoon spent down the rabbit hole.

Gilson still lives at the space, which is open most days from 1 to 5:30 p.m. I spent a significant amount of time studying the mirror wall, which has more than a dozen mirrors, as well as the psychedelic staircase. The exhibit is free, but donations are encouraged (hey, those credit cards don’t pay themselves).

Things to Do

Banjo Nights at the Elks is where it’s at on Wednesday nights. They have sing-a-longs. They have food and beverages for sale at a low price. They’re the best at finding great banjo players who light up the room, which is full of even more banjo players. This event is unique to Pittsburgh, and I was told to reserve my spot in advance unless I was willing to stand against the back wall for three hours.

The next night, I decided to channel my favorite “Whose Line Is It Anyway?” mood and caught a live improv show at the Arcade Comedy Theater. This place has shows Thursday through Sunday, including an all-ages show on the second Saturday of the month. Tickets are usually under $20, they have discounted tickets available and the theater is BYOB.

For the trip, I was hoping to squeeze in some time to check out the city’s Glass Center. They have a really nice studio and art gallery, and the center offers classes on a regular basis. The center also offers live hot glass demonstrations. The last time I saw a glass demonstration was in Italy, and it was absolutely amazing to see the worker spin a delicate horse out of a hot lump of glass. I ran out of time on this trip, but it’s at the top for the next time I’m in the city.

Food to Enjoy

One of my favorite things about traveling is trying the local food. There’s nothing better than eating something that a town really does right, like southern barbecue or New England clam chowder in the north.

Emil’s Lounge is the place to go when it comes to Pittsburgh. The restaurant is marked on the outside by a simple red awning. On the inside, however, they serve the best fish sandwich and the best Reuben in the city. This big claim is backed up by Food Network’s Andrew Zimmerman.

I was also able to enjoy Five Points Bakery in the Squirrel Hill/Point Breeze neighborhood. This bakery is family owned, and they pride themselves on making bread in the European tradition. While I didn’t have enough room in my stomach to finish a whole loaf, I made room when it came time to try their pastries. The packaging is delicate and attractive, so I picked up a cinnamon bun, chocolate croissant one of their decadent seasonal danishes for friends and family.

Two days in the city was not enough time to do everything I wanted to, but in an effort to keep myself honest on my next trip, here are the two places I’ll be checking out the moment I pass into the city limits.

While Pittsburgh is no longer the top U.S. whiskey producer, I’ve heard you can still get a glimpse of its heyday at Wigle Whiskey.


This distillery uses traditional copper pots to make its spirits, and it offers gin and rum for the non-whiskey fans. It is the most awarded distillery in the U.S., and it recently was a semifinalist for a James Beard award. I’ll also be journeying to Arsenal Cider house for its unique mix of ciders and fruit wines. It sounds like the perfect place to get some writing done. I’ll either sit amongst the interior brick walls and upright piano, or I’ll catch the breeze on the patio. Either way, I can’t wait to return to this historic city. Its moody streets do the soul plenty of good.

selfSam Casteris is an avid traveler and aspiring travel writer. She writes creative pieces about travel, informational articles for other travelers, and guides to make travel as stress-free as possible. Her home base is in Phoenix, AZ. Learn more at samcasteris.contently.com. 

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