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Fun Places to Go: My #1 Pick of the Year is Pittsburgh, PA!

Fun places to go: Pittsburgh, PA! Pittsburgh rivers and skyline are beautiful.
Pittsburgh has beautiful rivers and hills, plus amazing art and food!

Every year, I declare the best destination of my 365 days of travel that I think readers would most enjoy. The past two winners were classic vacation pleasers: the Caribbean island of Curacao, and fairytale Quebec City, Canada. Few of you, however, saw this year’s pick coming…

My favorite place I traveled this year was Pittsburgh!

Are you surprised??? Before visiting Pittsburgh, myself, I had only a hazy idea of what to expect — and I literally mean hazy. I pictured a steel mill with a gray cloud of haze over it. I was a fool!

I know that I am not alone in having underestimated the city. After getting the chance to tour it this past summer, I now passionately recommend Pittsburgh for your next trip.

The famous Pittsburgh "Point of View" sculpture of Washington and the Seneca leader, Guyasuta.
The famous Pittsburgh “Point of View” sculpture of Washington and the Seneca leader, Guyasuta.

What?! How can that be? Pittsburgh beat out my trip to the Colorado mountains and that gluttonous jaunt through Portland, Maine food scene? It did indeed, and not because I didn’t love the other trips of the year — because, WOW, did I ever — but rather, because Pittsburgh took my breath away with its unexpected BEAUTY.

Yes, Pittsburgh is topographically, artistically, culturally, and culinarily BEAUTIFUL. Above all, I had no idea that Pittsburgh is a visual symphony of rivers and hills.

Yummy emerald hills of Pittsburgh, dipping down to rivers.
Yummy emerald hills of Pittsburgh, dipping down to rivers.

Pittsburgh rivers and hills: Beautiful like Budapest?!

According to my friend Jeremy (the Pittsburgh blog expert who my husband, Colin, and I were visiting, and who inspired this whole trip), Pittsburgh has very similar topography to Budapest, Hungary. Ignorantly, this was not my image of Steel City at all before visiting. I didn’t even realize Pittsburgh had a single hill!

Though I have toured neither Buda nor Pest yet, I can see the similarity to Pittsburgh in photos now that I’ve visited the latter: snakes of rivers winding through hills, encircled with loops of arched bridges.

Pittsburgh has Budapest beat on river and bridge numbers, though. While Budapest has just the Danube River, Pittsburgh boasts the Allegheny, Monongahela, and Ohio Rivers… and to cross those rivers, you need a lot of bridge action.

Pittsburgh rivers and bridges
My husband and I had a great time in Pittsburgh!

How many bridges are in Pittsburgh? LOTS.

There’s a reason Pittsburgh is dubbed the “City of Bridges”: It has 446 bridges! Where do those even fit?! Happily, while these structures are useful to get from one part of the city to the other without getting drenched, they are also lovely to look at.

Gaze at the yellow arches leaping across the rivers in my photos, above. It’s almost as if the “Boing! Boing!” path of a lively squirrel was traced in the air with gold paint!

A saxophone painted house in City of Asylum, Pittsburgh.
A saxophone painted house in City of Asylum, Pittsburgh.

Pittsburgh food: Another reason I loved the city.

Your eyes can eat only so much beauty before your stomach begs for its share of sustenance… and Pittsburgh delivered! The highlight for me was Federal Galley: an incubator of several up-and-coming restaurant concepts in a welcoming, open space, which is the newest offshoot of the similarly-structured Smallman Galley.

For this indecisive, “I want everything” Libra, it was gold to walk into one room and have multiple restaurant choices for everyone in our party, but all get to sit at the same artsy wooden table.

Pittsburgh food: The Vandal
The food in Pittsburgh is incredible!

We will have to go back to the city soon to try the other Pittsburgh food Jeremy has been diligently investigating on his blog (hey, it’s a tough job, but my friend is hard-working). That said, I know you’re curious about my photo, above.

That was taken at brunch at The Vandal, a hip spot with food too beautiful for me not to photograph. My meal in that picture was as follows: Smoked trout, potato latkes, herbs, csalamade (Hungarian pickled vegetables), pickled egg, and roe (fish eggs).” Whoa, Pittsburgh! You’re yummy, and mighty creative.

Speaking of creative…

The decorated houses of City of Asylum, Pittsburgh.
The decorated houses of City of Asylum, Pittsburgh.

Pittsburgh art exceeds all imagination!

We’ve covered the glory of Pittsburgh’s rivers, hills and bridges, and the luscious nature of its food scene. What truly put the city into the #1 category for the year for me, however, was its art.

Sure, Pittsburgh museums are fabulous — the Frick, Mattress Factory, Phipps Botanical Gardens, Andy Warhol, and Carnegie Museum to name just a few — but it is the wild and hallucinatory street art that snagged my breath and heartstrings.

Fun places to go: Randyland Pittsburgh has colorful signs
Signs in Randyland: the most colorful house imaginable.

Randyland: One of the Most Fun Places to Go Imaginable.

At the very top of this list sits Randyland (click to see my full article about it, but prepare your jaw to drop). Randyland is an entire house courtyard and exterior — fully free and open to the public — decorated with every color of your hallucinatory dreams.

(Note: If you like Randyland, Bicycle Heaven is similarly quirky and fabulous: a must-see collection of over 3,500 vintage bikes.)

Randy (yes, there is a real Randy) is constantly adding to the decor and altering it, so, much like Graffiti Alley in Central Square of Cambridge, MA, you could visit every single day and still see something new each time. Just check out these Randyland stairs, pictured below…

Randyland Pittsburgh stairs
Me on the purple stairs of Randyland.

City of Asylum decorated houses inspire.

Right near Randyland are another row of brightly-painted houses, but this set has a whole different purpose. The City of Asylum is a sanctuary for persecuted writers from around the world. The designs on the outer walls of the buildings reflect the struggles these authors have faced, and their passion to brightly CREATE in a world that has tried to hold them back.

A brightly painted house in Pittsburgh's City of Asylum.
A vibrant painted house in Pittsburgh’s City of Asylum.

My favorite Pittsburgh architecture: Spiky PPG Place.

Moving downtown from those powerful exterior paintings, let’s discuss the delight of Pittsburgh’s spiky downtown architecture. The pointy-pointies center around PPG Place: the “Crown Jewel of Pittsburgh’s Skyline” which was completed in 1984, and conveniently looks like… a crown.

Though it’s not the tallest building in the world like a certain one in Dubai, the 40-story PPG Place astounds with its striking visuals and statistics. It is made of over ONE MILLION square feet of PPG’s own glass, and boasts 231 spires — the tallest of which is 82 feet high.

Like high buildings? Pitt’s Cathedral of Learning is absolutely breathtaking (and FREE to enter) and is the tallest educational building in the Western Hemisphere!

Pittsburgh rivers and skyline
“Heeeey, I like that spiky PPG Place skyscraper behind your head!”

While PPG Place looks awesome from afar as part of Pittsburgh’s skyline, I didn’t realize until Jeremy took us around downtown that there’s a whole glass spike-surrounded courtyard at the base of the skyscraper. This entire area is public space that hosts art installations, sitting areas for people to gather, and even a skating rink during winter!

Take another good look at Pittsburgh proper, because our next stop is to the splendid, bucolic region surrounding the city — ideal for romantic or family getaways beyond the downtown bustle.

Fun places to go: Pittsburgh architecture and PPG Place spiky courtyard
I love the spiky glass courtyard of PPG place.

Fun Places to Go Near Pittsburgh:

Laurel Highlands, Fallingwater, and Ohiopyle

The final piece which pushed Pittsburgh to my #1 destination of the year was this: Drive just an hour, and you’re in a tranquil countryside of rolling green hills in southwestern Pennsylvania known as the Laurel Highlands. My husband and I had a glorious three day visit to this region, and think you’d love it, too. Paired with a Pittsburgh stay, it’s a perfect vacation.

Think you’ve never heard of the Laurel Highlands before? Well, you likely HAVE encountered at least a photo of its most famous icon: the Fallingwater house by architectural genius, Frank Lloyd Wright! No visit to Pittsburgh is complete without seeing Fallingwater, and at less than a 90 minute drive from the city, it’s highly doable.

Fun places to go: The Laurel Highlands near Pittsburgh, PA
I was so happy in the green nature of the Laurel Highlands!

Check out Ohiopyle State Park as well, especially if you love rafting or hiking. Finally, I can’t say enough good things about these luxury cabins near Fallingwater for accommodations (we still dream of our room there!), and this sassy farm market for all your urgent fresh peach needs.

Given these rivers of perks, it should be clear, now, why Pittsburgh stole my heart this year. But what of the runner-up destinations which are also excellent ideas for your future travels?

Fun places to go: Luxury cabins in the Laurel Highlands near Pittsburgh
Freaking out about how awesome our cabin near Fallingwater was!

Runners up for fun places to go this year:

As much as I adored Pittsburgh, I cannot leave you without sharing some other highlights from my past year’s travels to get your vacation ideas cooking.

In South Carolina, Folly Beach proved a delightful island getaway, and the history of Charleston, SC bowled me over.

Out west in Colorado, the Rocky Mountains astound, and Boulder hikes can offer manageable day fun, along with great views and restaurant food scene.

In New England, Woodstock, VT emerged as a prime place to visit — walkable, charming, and surrounded by attractions from nature hikes to falconry. We also discovered why Portland, Maine has become rightly beloved for food.

In the Berkshires, MA region of Western Massachusetts, right at the border with New York State, Bash Bish Falls provides an excellent hike to the state’s highest waterfall — as long as you follow that link to my article to avoid the mistake we made!

Pittsburgh, PA is my favorite pick for fun places to go this year! I LOVED the Pittsburgh rivers, hills, art, and food, plus Laurel Highlands and Fallingwater. #travel #familytravel #Pittsburgh #vacation #vacationideas #pennsylvania
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Now, what are YOUR votes for most fun places to go of the year?

Have you visited any of the spots listed here? Do you agree that Pittsburgh has an immense amount of fabulousness to offer? Which spots (of the zillions it boasts) did I miss in pointing out? Do share!

Things to Do in Pittsburgh, PA

PGH has some of the most artistic, creative attractions around, and many of the best things to do in the city are FREE! Here are my favorites. Click through to learn more.

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Jennifer L Brommer

Monday 7th of December 2020

Your photos are stunning! We have never been to Pittsburg, but this post has inspired me to take a good look at making a visit here a reality. Thanks for the insight!

Julie

Monday 7th of December 2020

I've never been to Pittsburg, but now I'm totally convinced!! Food, art, and so many fun things to do- I'm in!!

Lillie

Friday 11th of December 2020

Glad to help sing a song of love for this great city!

Amanda

Sunday 6th of December 2020

Love this! I live in Pittsburgh (moved here 12 years ago) totally agree with this! Great recs for things to do in Pittsburgh.

Lillie Marshall

Sunday 6th of December 2020

You picked a great place to live! Glad you agree with the choices. I'm curious what other attractions Pittsburgh experts would suggest to hit first.

Ella

Friday 3rd of May 2019

Looks like such a fun trip!! The places and the food look amazing too!

Lillie Marshall

Monday 6th of May 2019

Woo hoo!

Robin

Monday 21st of January 2019

When I have had friends move there work over the years, they become Pittsburgh cheerleaders like you. I know it is worth a visit. Looking forward to finally seeing it!

Lillie Marshall

Monday 21st of January 2019

Glad to know I'm not the only one!

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