Actual Cool Things to do in Pittsburgh: Our Top 5 Picks for a Weekend Getaway

Checking out the coolest things to do in Pittsburgh - a weekend getaway.

It’s my birthday month — and if there is one thing that I’m good at doing, it’s stretching out a celebration! But this year’s big birthday destination pick even surprised Kevin. When I suggested Pittsburgh, he only had one thing to say — “Pittsburgh…Really??!” But listen up skeptics, Pittsburgh is on the rise. And well worth a weekend visit.

Inside the massive Church Brew Works, where they converted a chapel into a microbrewery complete with the original pews.

And oh yeah, did I mention that Pittsburgh is cheap? Even if you live all the way on the west coast, you can easily do this trip and keep it well within a cool budget. And besides birthdays, if there is one thing we love, it’s a deal!

One of the many gift shops with local artists channeling their Pittsburgh pride.

At one time, Pittsburgh was known more for its gritty steel plants and industrial factories rather than high art and trendy restaurants. But within the past few decades, the city has been re-inventing itself with community events and free yoga on the weekends in the main community square.

The crowd is out — free community yoga class in Market Square every Wednesday & Sunday during the summer.

And if that isn’t convincing enough, Pittsburgh is the closest major city to Frank Lloyd Wright’s architectural masterpiece Fallingwater (just 90 minutes south) and a long-time bucket list spot to see.

Fallingwater – just 90 minutes from Pittsburgh, and well worth the trek  

The city is compact so you can easily cram in a lot and never get bored. In fact, we did so much, I had a hard time narrowing it down. But after much thought, I came up with our top 5 picks for a weekend. And soon you’ll see why we think Pittsburgh’s so cool — and one of America’s best kept travel secrets.

5. Go Back in Time at Kennywood Amusement Park
Pennsylvania has it’s fair share of amusement parks. I grew up going to Hershey Park, Knoebel’s Grove and Dorney Park and Wildwater Kingdom. And while Kennywood was always on my radar, it always felt a little far from Northeast Pennsylvania. And ironically, now that I live in Los Angeles, I’m now making a cross country journey to visit.

Enjoying some Rita’s Italian Ice — a Pennsylvania treat — to cool down while waiting in line.

Kennywood ranks as one of the oldest amusement parks in America, and it feels very much like a time capsule. While Kennywood has some newer steel coasters, the park is probably best known for its rickety wooden roller coasters and other antique rides that haven’t changed much since they were built back in the 1920’s.

Enjoying the old-timey ride The Whip. Kevin wasn’t so sure about this one.

Walking through Noah’s Ark — a fun house meets Biblical story. Definitely not a combo I’d ever imagine would come together!

A lot of people compare Kennywood to Knoebel’s Grove (another historic amusement park in central Pennsylvania) and it’s easy to see why. Both parks offer a laid back, family park experience. And unlike Six Flags, you actually will find food that is delicious. Our friend — a Pittsburgh native — texted us a tip to eat the park’s signature food: fresh-cut fries from the Potato Patch. I’m glad we phoned a friend! These fries alone make a trip to Pittsburgh worth it!

Fries from the Potato Patch, named among the best fries in America… by us!

4. Walk Through Pittsburgh’s Tinseltown, “Hollywood of the East” 

The exterior shot of Allegheny County Jail, where several movies were shot, including cell scenes with Hannibal Lecter in Silence of the Lambs

Are you a movie buff? We certainly are. So when Kevin saw the “Hollywood East” tour operated by locally-owned Walk The Burgh, he signed us up right away. Pittsburgh makes a great backdrop with its three rivers, crossed by 446 bridges and a Manhattan-like downtown. Not only that, it’s cheap to film here. Pennsylvania started giving tax credits to movie productions, making it even more compelling for Tinseltown to set up shop.

Our guide shows us a scene from Fences, shot in Pittsburgh and written by Pittsburgh native August Wilson.

This 2-hour tour mixes history along with its general connection to Hollywood. If you want to freak yourself out, rent Silence of the Lambs and look for some of the city’s famous landmarks. You won’t get out to the suburbs to see Buffalo Bill’s creepy house. Or get to buy it anytime soon (our guide told us that the house recently sold for $195,000). You’d think a serial killer flick wouldn’t be a selling point, but hey, what do I know? There are plenty of movies less scary with Pittsburgh as the backdrop like The Perks of Being a Wallflower, Will Smith in Concussion, and even Tom Cruise running around the streets of Pittsburgh in Jack Reacher. And it’s not just movies coming to Pittsburgh. There is plenty of TV history including a must-stop at the Omni William Penn Hotel where you can find the original bubble machine used by Lawrence Welk. My dad would be in his glory here!

Checking out the original bubble machine used by Lawrence Welk, who filmed his show in Pittsburgh.

3. Eat Your Way Through Pittsburgh’s Famed Strip District

No trip to Pittsburgh is complete without a stop at Primanti Bros

The Strip District was one of our favorite neighborhoods in Pittsburgh for a number of reasons.  I love shopping, and this part of the city is home to a large number of international grocery stores, boutiques and souvenir shops. But besides the shopping, you come here to eat. And while there are a ton of great restaurants here, your first stop should be the original location of Primanti Brothers.

Outside the original Primanti Bros in the Strip District of Pittsburgh.

Even during the Great Depression Pittsburgh’s Strip District was a bustling hub of activity, with trucks transporting goods in and out of the city at all times of day. And everyone was looking for a good, hearty cheap meal. And that’s where their signature sandwich comes in. You can get it with beef or turkey or pork — or all three! Just don’t try to get it with fries on the side. The traditional way is to get the fries inside the sandwich. Load on the carbs!

Grabbing a seat at the counter is a fun way to see all the hustle inside. This place is hopping!

The street is also home to some other good food — though you likely won’t be hungry after the massive sandwiches at Primanti Bros. We recommend sharing the sandwich then walking the strip and eating the many free samples on hand at Mancini’s and the Pennsylvania Macaroni Co.

Free samples at Mancini’s — you won’t want to miss the garlic bread here!

Olive heaven at Pennsylvania Macaroni Co.

Bring on the cheese – Kevin wants to sample them all at Pennsylvania Macaroni Co.

2. Dine Among the Stars and Cable Cars at Altius

The view from Altius atop Mt. Washington is simply incredible — and we got a front window seat overlooking the three rivers and downtown Pittsburgh in its full glory. After a quick nap at the hotel, I was ready for some dinner! And it didn’t disappoint. The food was just as incredible as the surroundings.

Enjoying the delicious food at Altius

Besides eating (a lot!) of the bread, they brought out some popcorn before our entrees arrived. I’m not sure I’ve ever seen that at any restaurant (but I’m a fan!). Another quirky feature of the restaurant are the lights that flicker on and off. Altius shares the same power source as the Duquesne Incline, located just outside the restaurant. The incline still operates its original, ornate wooden cable cars dating back to around 1877. For full effect, be sure to ride the incline to get to the restaurant.

Kevin head inside the wooden cars of the old-time Duquesne Incline.

Views from the cable car.

Birthday surprise from Altius – a night out here is the perfect special occasion spot.

1. Learn What Ketchup, Mr. Rodgers and Football All Have in Common at the Heinz History Center

The original sets from Mr. Rodger’s Neighborhood, on display at the Heinz History Center

Finally, our number 1 spot! And while we loved pretty much every experience in Pittsburgh, the Heinz History Center went well beyond expectations. An affiliate of the Smithsonian Institution, this is the largest history museum in Pennsylvania. We recommend heading straight up to the top level where the world of Mr. Rogers is re-created. It isn’t a huge display — but you’ll find some of the the show’s most iconic sets and puppets on display. It will bring you back to your childhood.

Props on display from Mr. Roger’s Neighborhood

The History Center features six floors of permanent and changing exhibitions that tell the story of Western Pennsylvania. It can be overwhelming, but we skipped over the entire section on sports! One of the newest exhibits, and my personal favorite, was the history of the Heinz company. While its known for its ketchup, the company expanded internationally with a wide range of product lines.

One thing is certain – you can’t separate the Heinz company from Pittsburgh. And founder H.J. Heinz was a master marketer. He introduced the famous pickle charm at the World’s Columbian Exposition in Chicago in 1893, making the pickle pin one of the most famous promotional pieces of all time.

Our very own pickle pins.

We recommend at least 3 days in Pittsburgh, and we easily could have done even more. But I guess that’s a good sign. After all, Pittsburgh is a lot cooler than you may have ever imagined. And now I only want to eat all my sandwiches with french fries and ketchup on it!

Bye Pittsburgh – it’s been real.

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Actual Cool Things to do in Pittsburgh: Our Top 5 Picks for a Weekend Getaway
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Actual Cool Things to do in Pittsburgh: Our Top 5 Picks for a Weekend Getaway
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At one time, Pittsburgh was known more for its gritty steel plants and industrial factories rather than high art and trendy restaurants. But within the past few decades, the city has been trying to re-invent itself. Check out our top recommendations on cool things to do in Pittsburgh.

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