How to Spend a Day (or Two) in Pittsburgh – 2021

Pittsburgh PNC Park

Fifteen years ago I did something that would change my life forever. I moved to Pittsburgh.

I had friends and family all ask me hesitantly, “What’s Pittsburgh like? Is there anything to do there?” After fifteen years, here’s my response.  

This is Pittsburgh…

View of Pittsburgh from Mount Washington
View of Pittsburgh from Mount Washington

Were you expecting something different? Perhaps, a city covered in grime with clouds of smog blocking out the sun? A city where the darkness of noon resembles midnight? Those days are long gone, but for people who have never visited Pittsburgh, old reputations are hard to shake.

Pittsburgh has physical beauty, created by a unique mix of hills, rivers, and bridges, unlike anywhere else in the country. So, what is there to do in the “City of Bridges”? If I was visiting for a couple of days, here’s exactly what I’d do. 

If you can, visit in the summer. Pittsburgh is a phenomenal city year-round, but some of its finest attractions are best appreciated on a warm summer day.

Are you driving into downtown from the southwest? This includes anyone riding in from the airport. The odds are excellent you’ll go through the Fort Pitt Tunnel. Hopefully, your driver will give you a heads up, but if not, make sure you’re paying attention. As you exit the tunnel, you’ll be smacked with a visual feast I still admire after 15 years. For the first-time visitor – wham! Welcome to Pittsburgh!

Day One

Try to get to Pittsburgh around noon, which gives you two full days to explore the city. I recommend staying at the Omni William Penn Hotel, downtown and in the middle of the action. It recently celebrated 100 years, and while oozing with old-world charm, it’s gracefully kept up with the times. The lobby is a fantastic place to relax in between adventures with a coffee from the attached Starbucks.

I’ve been on dozens of food tours all around the world, so I can say without a doubt ‘Burgh Bits & Bites offers some of the best tours you’ll ever experience. Pittsburgh is a city with 90 neighborhoods, and you get to choose from half a dozen of the most walkable options. You’ll “…explore the vivid history and culinary delights of the Steel City…” with a small group f both tourists and locals. Just don’t eat before your tour as you’ll not only leave stuffed, you’ll have a bag filled with snacks for later. However, their Strip District Market tour is similar to tomorrow’s suggested activities, so if you’re interested, try it next time you’re in town.

After your tour, return to your hotel and fight the urge to slip into a food coma. There’s no time to nap. You’re going to a ballgame! Even if baseball’s not your thing, trust me. You’ll want to experience PNC Park.

You should have some time between the food tour and the ballgame, so make your way down to Market Square. It’s an easy walk from the hotel. The square was established in the 1700s, and it has gone through many stages, including crime-ridden a few decades back. Now it’s a pedestrian-friendly location lined with restaurants and bars. The square is used for dozens of activities throughout the year, from outdoor yoga to a Christmas market.

Now make your way to Point State Park. This is where Pittsburgh was born. You can still see the outlines of Fort Duquesne and Fort Pitt on the ground. These structures were built in the mid-1700s as the French and British vied to control the three rivers. For a brief history lesson on the forts and the Point, you can refer to Wikipedia.

Pittsburgh - Fountain at the Point
Fountain at the Point

You can’t miss the 150-foot-tall fountain near the point. You’ll likely see more ornamental, awe-inspiring fountains in your lifetime, but its simplicity and brute force are precisely what you’d expect from a Pittsburgh landmark. There may be no other fountain in the country more adored by the city where it resides.

Walk over to a bench close to the water and take a seat. It’s not often you get to see a river being born, so take it in. The Allegheny River to your right and the Monongahela River to your left come together to form the Ohio River. There’s something majestic about the powerful merging of the rivers and watching the water flow destined for someone’s Mardi Gras cocktail after the long journey south.

On your visit to the Point, have you noticed a lot of fans walking around in Pittsburgh Pirate’s gear? That’s because there’s a game tonight! So, get a move on!

From the Point there are many ways to get to PNC Park, but for an authentic game-day experience, cross the Roberto Clemente Bridge. The bridge, named after the Pirate’s most beloved player of all time, crosses the Allegheny River and is closed to cars before most games. If you look to your right, you’ll see the other two, “Three Sisters Bridges,” painted in iconic Pittsburgh Yellow.  It’s a festive atmosphere as fans stream over the bridge, accompanied by live music performed by street musicians.

The Clemente Bridge dumps you on the doorstep of PNC Park, the home of the Pittsburgh Pirates. It is one of the most beautiful ballparks in all of baseball, and the view is unparalleled.

Pittsburgh PNC Park
Pittsburgh’s PNC Park

While you can often walk up and buy tickets, you should order ahead in case there’s a high-demand special event such as Zambelli Fireworks Night. Pittsburghers love their fireworks! It’s a great show in you’re lucky enough to be in town for the spectacle.

You’ll want to grab seats down the first base line. You’ll have a phenomenal view of the scoreboard and the Pittsburgh skyline. If you’re high enough, you’ll be able to see the Allegheny River floating by.

If you’ve been dying to try a Primanti’s Sandwich, now’s your chance. No first-time trip to the Steel City is complete without trying one. An overflowing sandwich on Italian bread, topped with coleslaw and fries – what’s not to love?

For the ultimate Pittsburgh moment, grab a sandwich, some french fries doused in Heinz Ketchup, and an Iron City beer. Enjoy your meal with one eye on the game and the other on the skyline. If you’re lucky, you’ll catch a Gateway Clipper riverboat slowly gliding by the Clemente Bridge.

Once the ballgame is over, I’d recommend one of two options. If you’ve had enough and are ready to return to the hotel, find the North Side T-Station. The “T” is Pittsburgh’s light-rail system, and it’s free if you’re traveling on the North Side or downtown – very handy for getting around the city. The Steel Plaza station is close to the Omni William Penn Hotel, so exit there. If you’re up for a nightcap, the hotel’s lobby is a relaxing place to lounge.

However, if you’re a night owl, make your way back across the Clemente Bridge and hang a left on Penn Ave. You’re entering the Cultural District, which is filled with theaters, restaurants, and bars. Some standouts on this street are Proper Brick Oven & Tap Room, Nicky’s Thai Kitchen, and Bakersfield.

Day Two

If you like to get up early to run or walk, I highly recommend the North Side branch of the Three Rivers Heritage Trail. Cross the Rachel Carson Bridge and turn left on the other side of the Allegheny River to find the trail. You’ll be treated to fantastic views of the river, PNC Park, Heinz Field (home of the Steelers), and the city. If you are feeling ambitious, you can drop by Mr. Roger’s Memorial Statue. The 11-foot-tall statue has been called “lumpy” by some, but the real reason you’re here is for the scenery. You can’t argue he was left with a rather spectacular view of the city he embraced.

If you are feeling hunger pains, don’t worry. You’ll be eating soon.

Today I recommend a walk down Penn Avenue in the Strip District (the Strip). This neighborhood is home to some of the best restaurants and ethnic markets Pittsburgh has to offer. But don’t be foolish, and sit down to a big meal. The day is about grazing on an endless variety of tasty offerings. There’s no shame in sharing either. You’ll want to begin around 11 am to have enough time to do the Strip justice.

Start at the S&D Polish Deli and work your way toward downtown. If you’re not a borscht fan, you will be before you leave the Polish Deli. I traveled all over Poland and Ukraine, sampling the delicious beet soup in its motherland, so I have a good reference point. S&D’s offering holds its own. If you try it and you don’t like it, at least you’ll know you tried some of the best.

From 11 am until 3 pm, take in the Strip. Slowly make your way through the area, sampling food and checking out shops. If you’re in the market for some Steelers, Pirates, or Penguins gear, you won’t be disappointed at the number of stores.

The area has some of Pittsburgh’s best people-watching as it’s always bustling on the weekend. You’ll have plenty of opportunities to grab a drink and watch the world pass by.

Some of my favorite stops:

S&D Polish Deli – Borscht, pierogis, haluszki and more. For dining in, there’s a window toward the back of the store. Immigrants from Poland came to Pittsburgh to work in the steel mills in the 1800s, so there is an affinity for Polish food in the city, and S&D does it right.  

Lucy’s – This sandwich cart sits next to Bar Marco and serves the best banh mi sandwiches I’ve had outside of Vietnam. When Lucy runs out, she runs out.

The BeerHive – If you want to hang out with some locals and you’re in the mood for a cold beverage, you can’t go wrong with the BeerHive. There are usually a dozen beers on tap, many local, and the staff is always friendly.

Colangelo’s Bakery & Café – Everything is fantastic at Colangelo’s. If you’re in Pittsburgh, you have to try bean & greens. The Colangelo version is different than the standard version you’ll find at Italian restaurants across the city, but they’re still excellent. The café also serves the best macaroons I’ve ever tasted.

Pennsylvania Macaroni Company – Affectionately called Penn Mac by locals, this is the place to go for Italian groceries and more. To your left, as you walk through the front door, is a deli which can be a mob scene, but don’t let that scare you away. If you like cheese, you’ll be in heaven, and don’t be shy about sampling. Also, if you’re in the mood for dessert, there is a large selection of Italian favorites.  

Roland’s Seafood Grill and Iron Landing – a.k.a. simply Roland’s, has the best people-watching location in the Strip. There are approximately 30 tables on the sidewalk and the balcony above. I can’t vouch for the menu here as I’m usually taking a food break, but it’s always full of happy-looking eaters. There are dozens of beers on tap, and the restaurant has a full bar.

Wine Library in the PA Market – If you prefer wine, or it’s a boiling hot day, and you’re looking for coolness, the Wine Library is an excellent place to relax. The brick walls, wood floors, and comfortable couches make you feel like you’ve entered a friend’s living room – a wealthy friend.

Edgars Best Tacos – Edgar’s is the most challenging restaurant to find in Pittsburgh. It is continuously on the move, but a loyal fanbase follows wherever it goes. And for a good reason, because Edgars has incredible street tacos and more. Make sure you save some room for this stop. I’m drooling as I write this.  

Wholey’s Market – Wholey’s has been around for over a hundred years and is the place to go in Pittsburgh for seafood. The market is usually hopping, and it’s an interesting place to visit, even if you’re stuffed to the gills at this point. However, Andy’s Sushi at Wholey’s should not be missed if you’re still going strong. Just follow the long line of people and wait for your turn. You’ll be happy you did.

Also, if you’re looking for something to take home, dozens of quirky stores in the Strip sell local items you won’t find anywhere else. There are even some non-food places!

At 3 pm, it’s time to get educated. You’ll have two hours to explore one of three museums, depending on your interests.

Senator John Heinz History Center – 250 years of Pittsburgh history is under one roof. This museum is my favorite of the three, but I’m partial to history. As luck would have it, or good planning, it’s located in the Strip and should be an easy walk for you. If you want a better understanding of the city you’re visiting, you’ll find it here.

Pittsburgh Warhol Museum
Pittsburgh Warhol Museum

The Andy Warhol Museum – Art lovers, and especially fans of Andy Warhol, should grab a ride to the North Side. You’ll find the largest museum in the U.S. dedicated to a single artist. Immerse yourself into the world of Warhol as you admire his paintings, prints, sculptures, photographs, and movies. You’ll not only come away with a better understanding of his work but of his life as well.

Carnegie Science Center – The most visited museum in Pittsburgh is ideal if you have children, but even if you don’t, you’ll be able to keep busy. Highlights are the Buhl Planetarium and the Miniature Railroad & Village. I’m not sure what it is about miniature railroads, but I often find them fascinating. Apparently, I’m not the only one, as this diorama has been around for 50 years. The trains are surrounded by a miniature depiction of 1880 to 1930 Western Pennsylvania, which adds character to the display.

Each one of these museums is going to kick you out at 5 pm, but that’s ok because it’s time for dinner! In case you haven’t noticed, I like food. You’ll want to gussy up a little for tonight, but business casual will do as Pittsburgh still embraces its blue-collar past and is not a pretentious town.

Make your way to the Monongahela Incline, which has been around since 1870. You’ll be treated to phenomenal views of the city as you make your way to the top of Mount Washington. Actually, this entire evening is about taking in the city of Pittsburgh from a magnificent vantage point.

This area, overlooking the city, was a prime source of coal when the incline was built and was named Coal Hill. I’m guessing Mount Washington sounded better in travel brochures, so the name was changed.

Exit the incline station and take a right. You have about a mile to walk until your next destination, but you’ll be enjoying panoramic views of the city the entire way. There are several viewing platforms you will pass for a closer look.

Keep an eye out for the Duquesne Incline, which will be on your right. If you are interested in the workings of an incline, head inside and take a peek. You’ll get a view of the machinery that powers the car to the top of the hill. Also of note are pictures of the Pittsburgh flood of 1936. It is a stark reminder downtown sits between two powerful rivers. The flood caused billions of dollars in damage (in today’s dollars) and killed 45 people. The pictures of the event are striking.

A handful of restaurants sit at the top of Mount Washington and offer impressive views of the city. My favorite by far is Altius. It’s hard for me to adequately describe their cuisine, so I won’t, but here’s their menu. If you are unable to get reservations, or you’d like to reduce your bill a touch by sampling apps, the restaurant has a fantastic bar with the same great view. Service is outstanding wherever you sit. I always start with the charcuterie and branch off from there.

The desserts are certainly worthy at Altius, but you may need some time to walk off your dinner, and I have another location for you to visit. Exit Altius, take a right, and walk to the Monterey Bay Fish Grotto. You’ll take an elevator to the restaurant and then walk down one floor to the bar. I almost hate to give this secret away as the bar is typically used only by guests waiting to eat dinner, so it is rarely packed. You should be able to find a table in front of floor-to-ceiling windows overlooking a nighttime Pittsburgh.

Pittsburgh at Night
Pittsburgh at night

The bar is a wonderful place to grab a mixed drink or glass of wine. Also, if you’re a chocolate lover, I highly recommend the Chocolate Latte dessert. It’s not coffee but a flourless chocolate cake made to resemble a latte. This cake is in my top 5 desserts of all time.

If you are lucky enough to be in Pittsburgh during a firework display, and trust me, there are many; the Monterey Bay Fish Grotto Bar offers a unique viewing experience. Have you ever seen fireworks from above? This is your opportunity to see the show from a spectacular vantage point, high above the city.

Day 3

It’s getaway day, and I’m sure you have important things to do back home. However, consider dropping by DeLuca’s Diner in the Strip if you need some nourishment for the road.

“Home of the best breakfast in town,” DeLuca’s has been around since 1950. The line out front that extends down the sidewalk doesn’t lie. It’s a Pittsburgh institution and extremely popular on the weekends, but if you arrive early enough, you should be able to get in quickly.

There’s no need for me to make suggestions on what to order at DeLuca’s. Scan the menu, and rest assured whatever you order will be incredible and probably enough to feed two. After your meal, push away from the table, roll out into the street, and head home knowing you crushed Pittsburgh.

Finances

I hear you – “Sounds great, but what’s it going to cost me?”

I’m all about budgeting and finances, so I’ve done my best to estimate prices and the most likely expenses you’ll have. A weekend in Pittsburgh, as outlined, will cost you about $1,200 for two people. If you eliminate the most expensive dining options, you should be able to spend closer to $1,000.

Lodging$338$338
Food & Beverage518343
Food Tour9797
Pirates Tickets6060
Pittsburgh Swag9090
Museum4040
Uber/Lyft/Taxi5555
Incline55
Parking2626
   
Total$1,229$1,054

Your mileage may vary depending on the weekend, if you really like to eat (hand raised), and your transportation expenses before arriving in the city. 

If you’ve never considered visiting Pittsburgh, it’s time to right the wrong. I’m not a native but after 15+ years I’ve grown to love the city and all it has to offer. You won’t be disappointed!


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    Financial Advisor David Tuzzolino

     

    David Tuzzolino, CFA, CFP®, is the Founder and CEO of PathBridge Financial, a firm that specializes in providing comprehensive financial planning and investment management services for clients that are nearing retirement and love to travel.