Fun Things to Do in Pittsburgh for an Amazing Weekend Trip

There are so many fun things to do in Pittsburgh that will make you want to plan a weekend there ASAP. I really wasn’t expecting to fall for Pittsburgh. A former steel manufacturing city, Pittsburgh was just as much the “Steel City” as the “Smoky City,” named for the dense smog that permeated the streets.

However, Pittsburgh is continually reinventing itself following the collapse of the steel industry. It’s atop the list of world’s most livable cities and recently, the top 100 places to live in the USA. There are many reasons to fall in love with Pittsburgh, many of which I discovered only after visiting the city for a few days.

From the food and drink scene to the city’s endearing quirks, my trip to Pittsburgh really left me wanting more. Here are my favorite things about the “City of Bridges”. (Pittsburgh has a lot of nicknames!)

Where to Stay in Pittsburgh

Let’s start with where you’re going to rest your head at night. If you’re planning a great weekend in Pittsburgh, staying at a swanky hotel is always a good idea. You’re going to fall head over heels with the city by staying at the Hotel Monaco by Kimpton. Centrally located downtown, the Hotel Monaco has artist inspired designs from the public spaces to the individual rooms.

This hotel is simply stunning, from the common areas to the private rooms. It’s chic, artfully designed, and has lots of great amenities like an amazing fitness center. This is a pet-friendly hotel in Pittsburgh. There’s also an on-site restaurant, a seasonal rooftop beer garden, and complimentary bike rentals.

The rooms have city views or park views, comfy beds, and fully stocked mini bars. There’s a flatscreen TV with premium channels. The bathrooms have high quality bath products, too. I really just love the little details and style of the room. What do you think?

How to Get Around Pittsburgh

While some areas of downtown Pittsburgh will be within walking distance of the hotel, other attractions and activities are spread across the city. I recommend renting a car when you visit so you don’t need to limit what to do in Pittsburgh.

I suggest comparing the best rates for car rentals with Discover Cars. You can compare the prices of several rental car companies to find the cheapest rates in town. Browse car rental prices in Pittsburgh here.

Pittsburgh also has an excellent public transit system with buses and light rail, which includes transportation from the Pittsburgh International Airport. There’s also a Hop On Hop Off bus where you can learn a bit about the city as you travel from place to place.

Renting bikes is also a fantastic way to get around Pittsburgh. You can rent and return bikes using the Healthy Ride system at over 100 stations throughout the city. I also recommend taking a bike tour around Pittsburgh, which I will detail later in the blog post.

Fun Things to Do in Pittsburgh: Check Out the Epic Skyline

Pittsburgh’s unique skyline truly sets it apart from other cities. The scenery pairs skyscrapers with numerous bridges dotted across the river. There are a few excellent ways to explore the skyline and discover new perspectives of the city. Taking a boat cruise on the Gateway Clipper and riding the Duquesne Incline are among the best things to do in Pittsburgh, PA.

Take a Cruise on the Gateway Clipper

A sightseeing cruise aboard the Gateway Clipper is a fantastic introduction to the city and one of the most fun things to do in Pittsburgh. It’s a great way to view the waterfront landscape along the Allegheny, Monongahela and Ohio Rivers. The captain and an employee narrate fascinating stories and facts, so it’s a great way to get acquainted with a new place.

You’ll see and learn about historic landmarks, significant buildings, and drift beneath many bridges. You’ll also get first hand knowledge from Pittsburgh locals about what it’s like to live in the city. I also loved hearing all of the personal stories and historic tales that give more depth and background to the sights.

Pittsburgh Tourist Attraction: The Duquesne Incline

A trip to Pittsburgh isn’t completely without a ride up the Duquesne Incline. One of the most popular Pittsburgh tourist attractions, visitors can ride the iconic red trolley car to the top of Mt. Washington for an epic view of the city.

The Duquesne Incline was originally built in the late 19th century to carry cargo up and down the mountain. Nowadays, this historic attraction transports people back and forth. It’s one of the best things to do in Pittsburgh, and something you must do on your first (and second, and third) visit. The scenery from the top is outstanding!

What to Do in Pittsburgh: Discover the Arts Scene

Pittsburgh is a city with a vibrant arts and culture scene, from museums to public art. There’s so much to discover that you’ll need more than a weekend in Pittsburgh. If you’re planning to stay for two days in Pittsburgh, three days in Pittsburgh or longer, these are great ways to fill your itinerary.

Plus, if it happens to rain while you’re there, these are some of the best indoor activities in Pittsburgh that are open all year long. If you’re visiting Pittsburgh in the winter, you’re going to want to escape the cold into one of these top art galleries.

The Andy Warhol Museum

The Andy Warhol Museum is one of the best things to see in Pittsburgh. If you’re a fan of Andy Warhol and his art, this is a must visit spot.

Become immersed in Warhol’s life and legacy as you wander around this eight floor museum. Andy Warhol was born in Pittsburgh and this is the largest collection of his works. This is also one of the most comprehensive single-artist galleries worldwide.

The Mattress Factory

The Mattress Factory is a must visit for lovers of modern art. You can interact with most of the artwork and become a vital part of the experience. There are temporary and permanent installations, including two by Japanese artist, Yayoi Kusama.

I could easily see this being one of the best date night ideas in Pittsburgh if you visit during their longer hours of operation on a Wednesday evening. A trip to The Mattress Factory, The Andy Warhol Museum (or both!) are some of the fun things to do in Pittsburgh for arts lovers.

Pittsburgh Street Art

You don’t need to enter a museum to witness the art of Pittsburgh. Simply walk around the neighborhoods to uncover it for yourself. I enjoyed coming across street art and colorful murals all over town.

There’s a great Pittsburgh street art account on Instagram that you should check out to find these beauties all over town. Discovering street art and public art is one of the top free things to do in Pittsburgh, Pennsylvania.

Visit Pittsburgh Historic Sites

Pittsburgh and Allegheny County have preserved hundreds of historic sites and landmarks that contribute to the vibrancy of the city today. It’s important to protect architectural relics in order to maintain them for future generations.

Station Square

Station Square is a shopping and entertainment complex, redeveloped from the site of the old Pittsburgh Terminal Train Station. Bessemer Court, at the heart of Station Square, pays tribute to Pittsburgh’s history as a steel manufacturer. The Waltzing Waters fountain is a beloved spot where the water is choreographed to popular music.

And on the way from Station Square to the Gateway Clipper, there’s a bridge painted with murals celebrating the history of Pittsburgh. Walking around the Station Square area is one of the best things to do in Pittsburgh for history, art, and great views of the river.

Penn Brewery

The restored Eberhardt and Ober Brewery building is a historic site and current home to Penn Brewery. Three remaining buildings make up the Penn Brewery site, and all three are on the National Register of Historic Places. Penn Brewery was one of our stops on our beer tour of Pittsburgh, which I’ll mention in a moment.

Next to the patio, you can see the 150 year old lagering caves, dug into the side of Troy Hill. They used to keep the beer at a constant 55 degrees, long before refrigerators were invented. Penn Brewery is not only the oldest and largest brewery in Pittsburgh, it’s one of the only remaining breweries in the United States with lagering caverns.

Fun Things to Do in Pittsburgh: Craft Beer Tour

Speaking of beer, Pittsburgh has a growing and thriving craft beer scene. New ones are always emerging and it seems like you have endless refreshing options. If you’re not sure where to start, take a tour with Pittsburgh Brew Tours. We were transported around in their van, and we didn’t have to worry about driving ourselves around town.

You can try a variety of different brews at several breweries, all with interesting back stories and delicious beer. At each location, we went behind the scenes to observe the brewing process with a glass of beer in our hands. We got to taste a variety of samples at each location, too. It’s one of the most fun things to do in Pittsburgh, hands down. Other than Penn Brewery which I already mentioned, here are some of the breweries we visited.

Hop Farm Brewing Co

Hop Farms produces tasty beer while focusing on sustainability and local ingredients. They produce saisons, hoppy IPAs, porters and stouts. Hop Farm is always trying new flavours that rotate on a seasonal basis.

Allegheny City Brewing Co

Allegheny City Brewing Co in the Deutsche Town Neighborhood served all sorts of inventive flavors of beer. The “Serviceberry Wild” is a sour ale with service berries, aged in red wine barrels. The “Starlake” is a wheat ale with red raspberries and white tea.

For the beer purists out there, Allegheny City also has more traditional brews, such as their Belgian-style ale or a brown ale.

Pittsburgh Distilleries: Wigle Whiskey

Departing from the topic of beer, let’s move on to spirits in Pittsburgh. Spend some time at Wigle Whiskey to check out the barrelhouse, the tasting room, and the whiskey garden.

Pittsburgh was the epicenter of American whiskey production dating back to the 1700s. Wigle Whiskey continues this tradition, even winning numerous awards. Wigle is recognized as the most awarded distillery by the American Craft Spirits Association.

Sample the whiskey and try a cocktail or two! The whiskey garden is a large, outdoor event space and we were fortunate enough to have lunch there. Local chef Rafael Vencio created a three-course delectable lunch, all paired with whiskey. Events range from cocktail classes to live music, so you can easily spend a few hours at Wigle.

Explore the Pittsburgh Vegan Scene

Thankfully, vegan options in Pittsburgh are plentiful. You won’t go hungry while maintaining a plant-based diet. While there are a number of vegan restaurants like Apteka and B52 Cafe, you can find vegan menu options at many restaurants.

Here are a few spots that I had the chance to try. I can’t wait to return to Pittsburgh to try even more vegan restaurants, which I’m sure are even more plentiful since my visit a few years ago. Eating and drinking is one of the most fun things to do in Pittsburgh, and going vegan is no exception to this.

The Vandal

For breakfast, try visiting The Vandal. The chef is very aware about vegan diets and even if there’s nothing on the menu, I’m sure that something can be prepared for you. I enjoyed toasted sourdough with a local jam, as well as a beautiful fingerling potato and vegetable dish.

Enrico Biscotti Bakery and Cafe

For lunch, head to the Strip District and dine at the famous Enrico Biscotti Bakery & Cafe. Their pizzas are cooked in wood fired ovens. Order the kale and white bean dish to start and a vegan pizza as your entree (ask for no cheese and vegetable toppings). The dough is chewy and just perfect.

More Vegan and Vegetarian Restaurants in Pittsburgh

Treat yourself to one of several vegan / vegetarian restaurants in Pittsburgh:

• Apteka – Central and Eastern European cuisine
• Onion Maiden – Asian and American comfort food in a punk/heavy metal themed setting
• Randita’s Organic Vegan Cafe – Wraps, burgers, salads and smoothies

Best Things to Do in Pittsburgh: A Bike Tour

To discover the best of Pittsburgh’s bike paths, take a guided bike tour around the city. Our guide lead us all over town while explaining interesting facts about Pittsburgh on frequent stops on the way.

We got to ride across bridges and along waterfront paths. I never realized just how accessible Pittsburgh is by bicycle. You can really see a lot of the city by bike, and I highly recommend it.

Even if you’re visiting Pittsburgh and don’t want to book a full tour, you can rent the bicycles on their own by the hour. Try to book the guided tour if you can as it’s well worth it. Whether you explore on your own or take a guided tour, riding bikes is one of the most fun things to do in Pittsburgh.

If you’re more of a fan of walking tours than bike tours, don’t worry – here is an amazing walking tour that you can take called Best of the Burgh!

Cool Things to Do in Pittsburgh: Explore Neighborhoods

Pittsburgh has dozens and dozens of neighbourhoods, some only spanning a few blocks. While I fully intend to travel back to Pittsburgh to explore more of the neighborhoods, there’s really something for everyone here.

There’s the market vibe of the Strip District if you’re looking to shop for fresh produce. Lawrenceville is a little more trendy and artsy. Shadyside has high end boutiques, while Squirrel Hill offers more shopping experiences.

Sewickley has streets lined with trees, great restaurants, and night markets in the summer. The idea of visiting several different neighborhoods on my next visit to Pittsburgh is fueling my desire to return.

Quirky Things About Pittsburgh

Pittsburgh is definitely one of the most unique American cities! There are lots of things that are common place among locals that you won’t find anywhere else. Live like the locals do – I’m going to tell you a few things to know about Pittsburgh before you visit.

Pittsburghese: The Language of Pittsburgh

Through spending a couple of days in Pittsburgh, I learned about some of its quirks. For instance, the residents have their own language, known as Pittsburghese. There are different pronunciations and even entirely new words for things.

The word ‘yinz’ means you (when there is more than one person). People from Pittsburgh might say ‘how’s about’ instead of ‘how about’. Much like in Canada, soft drinks are called ‘pop’ instead of ‘soda’. There are tons of variations of the English language when you arrive in Pittsburgh, so you’d better study up on your terminology.

They Put Fries on Everything

Fries on everything? Now that’s something I can get behind. The 24-hour diner, Primanti’s offers their famous sandwiches topped with coleslaw and fries. Pittsburghers even like to put fries on their salads!

Now that you know all of the amazing and awesome fun things to do in Pittsburgh, it’s time to plan your visit. While I suggest visiting Pittsburgh in the spring, summer, or fall to take advantage of the outdoor activities, you could really visit any time of the year.

If you’re interested in more city guides around the USA, take a look at these related blog posts. Also, feel free to take a look and browse all of our United States articles.

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What do you love the most about Pittsburgh?