The Perfect 3-Day Weekend in Pittsburgh

I grew up just two hours north west of Pittsburgh in Erie, Pennsylvania. That was the ’80s and ’90s and back then there wasn’t much of a reason to make the drive to Steel City. I grew up during the time that Pittsburgh’s steel industry began to implode and the population was leaving. Aside from passing through and a school field trip to the Carnegie Museum of Natural History, I’d never properly visited during my 18 years growing up in Western Pennsylvanian. A weekend getaway in Pittsburgh wasn’t on many Erieites radar, unless you were visiting one of Pittsburgh’s colleges or universities.

When Pittsburgh’s tourism bureau invited me to come discover the city, I thought why not? High school friends wanted to know what the heck I could possibly be doing in Pittsburgh. As comments from friends that had went to college and then left Pittsburgh before the big revitalization started in 2002 began to pour in, I started to wonder myself.

But what I found is a vibrant city with a cool cultural scene. It also quickly became evident why Pittsburgh has been named the nation’s “No. 1 Food City” by Zagat. Add in that Steel City is inexpensive, has loads to see and do and is an easily walkable city, and you’ve got a completely underrated destination for perfect 3-day weekend getaway in Pittsburgh.

Day 1: Kayaks and Cocktails

Breakfast isn’t the big meal of the day in Europe, but when I travel I like to indulge. And indulge I did kicking off my trip to Pittsburgh at Waffles, INCaffeinated where an Eggo drizzled with syrup simply won’t do. No, here the waffles are over-the-top with seven signature gourmet waffles including both sweet and savory.

Never able to pass up eggs benedict, I opted for the eggs benedict savory waffle topped with Canadian bacon, crab, perfectly poached eggs and dressed with just enough hollandaise sauce.

Thankfully I was immediately working off breakfast with a little urban adventure. Kayaking the Allegheny River turned out to be my favorite way to take in Pittsburgh’s beautiful skyline. Kayak Pittsburgh actually has three locations and we started out on the North Shore under the 6th Street Bridge. A gorgeous late morning was spent paddling under just a few of Pittsburgh’s 445 bridges, while spotting some of Western Pennsylvania’s wildlife like herons and beaver.

Also located in the modern North Shore neighborhood is the Andy Warhol Museum. Though I’m definitely family with Warhol’s iconic Campbell’s tomato soup can painting, I guess I never realized he was born and grew up in Pittsburgh not far from where the museum resides today. Normally wandering an art museum wouldn’t be my cup of tea, but I do like pop art and the Andy Warhol Museum is filled with his wonderfully weird creations. Well worth the 90 minutes or so it takes to explore all seven floors.

Venture over to the Strip District  for lunch at Smallman Galley, which is a play on the famous food halls of Europe. Started by two former Navy guys turned entrepreneurs, up-and-coming chefs go through an application process to win one of four coveted kitchens located within Smallman Galley. With unique menus at the four mini restaurants, there’s sure to be something for every palate – or you can sample all four as we did.

The chefs staff their kitchens, but Smallman Galley provides the rest including the educational component of managing your own restaurant. As we tasted small plates from each of the four chefs currently in residence, two told me that they’ve rented space and are opening their own restaurants right in Pittsburgh once their 18-month program at Smallman Galley concludes.

While in the Strip District, swing by Wigle Whiskey.

I probably shouldn’t admit this as someone who writes about wine and spirits for a living, but once you’ve toured one winery or distillery it often feels like you’ve toured them all. Each might have their own special way of doing things, but the process of turning grapes into wine and grains into alcohol just doesn’t change all that much. Wigle Whiskey does it differently though.

First, the tour begins with selecting a craft whiskey cocktail from Wigle’s cantina. With a fantastic cocktail already in hand, I knew this would be a fun tour. What my grade and high school history classes never taught me is that Pittsburgh is the birthplace of American whiskey. Yes, even before there was Kentucky bourbon there was Pennsylvania rye.

We got a very animated history lesson as we toured the Wigle Whiskey distillery before a tasting of their various whiskeys and bitters. You definitely won’t want to miss a visit and though I’m not usually a whiskey drinker, I’m still craving the whiskey cocktail with rhubarb and rosemary-lavender bitters. So good!

If you can find a little more room, pop by the original and flagship location of Primanti Bros. It’s now a chain in Pennsylvania and a few other Eastern US cities, but not an unimaginative American chain. The James Beard Foundation named them an American classic and the “almost famous” sandwich is even a Pittsburgh landmark.

Opened in 1933, Primanti Bros. is famous for their grilled meat sandwiches with a heap of fries stuffed between two thick slices of Italian bread. You can’t leave Pittsburgh without trying one and if you’re unsure what to get, like I was, the pastrami is their best seller.

Day 2: Urban Exploration around Pittsburgh

It’s a good thing Pittsburgh is such a walkable city, because you won’t want to miss some of the tastiest pancakes I’ve ever had. They are Pamela’s Diner’s legendary crepe pancakes. You can get them stuffed with things like strawberries or bananas foster, but I opted for just a plain stack.

President Obama is a fan too. He even took time to tell reporters about them when he was on the campaign trail and visited back in 2008. “Before I answer this question, these really were maybe the best pancakes I’ve tasted in a very long time. Get some take-out,” Obama directed the reporters. “You don’t even need syrup on them. They’ve got these crispy edges. Yea, they are really good.”

Next, head to the Oakland neighborhood where the Gilded Age meets urban campus.

I was so anxious to escape Western Pennsylvania, that I never even considered attending a university in the state. Life sure would have been different and I may have never met Tim if I hadn’t moved to Las Vegas, but touring the University of Pittsburgh’s Cathedral of Learning Nationality Rooms almost made me wish I’d considered attending Pitt.

Thirty classrooms have been curated into national heritage rooms that teach students, and visitors like us, about the good things immigrants brought to America. The classrooms are actively used, but you can tour and see a variety of rooms depending on which are open during your visit. We’ve actually been to all the countries’ rooms that we visited during our tour and it was fascinating to recognize the details that have been incorporated into each of these unique classrooms. There’s truly nothing else like it anywhere else in the world.

Just a few minutes from the Cathedral of Learning is Phipps Conservatory. The rooms and gardens filled with colorful orchids and seasonal plants and flowers are sure to make you forget whatever is happening outside. The exhibits change seasonally and each of the more than 20 rooms have a theme.

My favorite was the orchid room since my favorite flower is orchids. There’s even an orchid that smells like chocolate!

Pittsburgh has 90 different neighborhoods that make up its metropolis and The Strip District is one of the most thriving of them. That’s probably why I just couldn’t stay away.

This neighborhood is full of history; it was here that mills and factories set up along the Allegheny in the 19th century. Immigrants saw an opportunity, opening wholesale shops and restaurants to feed the blue collar workers. And today, The Strip District has remained full of unique family-run businesses with the exception of one chain: McDonald’s.

The biggest problem is knowing which places are a must-try. ‘Burgh Bits and Bites Pittsburgh food tour solves that problem and lets you sample a variety of the best of The Strip District while learning the history of this unique neighborhood. Pierogis, pizza rolls and cinnamon toast were fond reminders of things I grew up with just two hours north-west in Erie, Pennsylvania. And the fun tour solidified my belief that a food tour is one of the best ways to discover a city.

Walk off the food and make your way across the city to the Duquesne Incline. The historical gauge railway dating back to 1877 sweeps you up Mount Washington to the very best view over the city. You’ll definitely want to be here for sunset and if you’re blessed with gorgeous weather as we were, Pittsburgh’s sky will most definitely put on a show for you.

This spot is a photographer’s dream with the city’s colorful bridges and towering skyscrapers serving as a backdrop for the confluence of the Allegheny, Ohio and Monongahela Rivers. As the sun begins to dip in the sky, the once blackened Steel City glistens in shades of gold. And after dark, the city lights twinkle below.

Treat yourself on this last night with a meal at one of Pittsburgh best and most upscale restaurants: Monterey Bay Fish Grotto. As the name implies, this riverside restaurant with panoramic views over the Golden Triangle is known for its elegantly plated fish and sea food, though the menu features dishes for the landlubber too.

All the fish is either from locally or is flown in fresh within 24 hours of being caught. The crab cake stuffed giant sea scallops and lobster mac and cheese are to die for.

Day 3: Brunch with the Owls

Did you know Pittsburgh is home the nation’s largest zoo dedicated to birds? We didn’t either! With open air exhibits, you can interact with a variety of birds like flamingos and finches at the National Aviary.

My favorite exhibit was the Grasslands, where tiny, colorful birds zip all around the room and in and out of their nests. There’s also a baby sloth sure to melt your heart.

The National Aviary also has special events like brunch with the owls or dinner with the penguins and we got to dine with both during our special private visit. Having Golide, an African penguin, entertain us with her cute antics while we had a catered dinner was truly a highlight of our visit.

Where to Stay in Pittsburgh

The Hotel Monaco Pittsburgh is in the heart of downtown Pittsburgh and just a 10-minute walk from the Pittsburgh Amtrak, making it an excellent and easily accessible base for your long weekend in Pittsburgh. Hotel Monaco is a boutique luxury hotel housed in a strikingly beautiful building from 1903 and it has a rooftop beer garden serving Pennsylvania craft beers and craft cocktails with lovely skyline views.

The hotel offers a happy hour with a complimentary glass of wine for guests each evening and other complimentary amenities like wifi and spa water are nice touches.

The large rooms are chic and lively with bright decor. I even got some design ideas, like the painted wardrobe, to try out at home. Best of all, Hotel Monaco is pet-friendly.

Traveling to Pittsburgh

If you’re Pennsylvania or East Coast based, Amtrak is an excellent alternative to getting to Pittsburgh. Parking and traffic can be a bit challenging in downtown Pittsburgh, but the city is easily walkable and well-connected with public transportation to get about during your long weekend. Check out GoTicket for all the train and bus transportation options getting to and around Pittsburgh.

Alternatively, Pittsburgh International Airport is just a 30-minute drive from downtown and serviced by many airlines.

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My trip to Pittsburgh was in partnership with Visit Pittsburgh in order to bring you this story. However, Luxe Adventure Traveler maintains full editorial control of the content published on this site. As always, all thoughts, opinions, and enthusiasm for travel are entirely our own. This article contains affiliate links. When you shop on Amazon or book on Booking.com through our affiliate sites, we earn a small commission at no additional cost to you.