48 Hours in Pittsburgh | The Ultimate 2021 Weekend Itinerary for Pittsburgh

Post by 
Jenna Gnieski

So, you’re thinking of taking a weekend trip to Pittsburgh? Good thing we’ve got the ultimate weekend in Pittsburgh itinerary for you. By the end of this trip, you’ll be the newest Yinzer in town.


Where to Stay in Pittsburgh

As a property management company, we do more than just leasing apartments. We’re in the short-term rental business, too!

And as Pittsburgh natives, we know the best neighborhoods to live and play in. In fact, many of our short-term rental properties are located in our favorite areas of the city.

Rent With Us

If you book with us, we’re offering a 10% discount since you came from the blog - what a perk! Use code ‘PGH10’ on our direct site or through Airbnb!

Pet-Friendly Studio

This stay is a modern studio in Pittsburgh near the quiet towns of Green Tree and Crafton. It’s located 5 miles from Downtown Pittsburgh and is perfect for 1-2 people (and pets)!

Book now

Pittsburgh Short-term Rental / AirBnb property, Birgo Realty

Historical Studio Apartment Near Stadiums

Stay at this brand new historical renovation themed as the Poet's Library! It’s just a 10-minute walk to Heinz Field and the rest of the sights of Pittsburgh’s North Shore. 

Book now

historical short term rental / Airbnb on Pittsburgh's North Side

Fully Furnished Loft with Parking

This space was renovated from an organ warehouse factory in historic Allegheny City to a sleek loft apartment. It’s centrally located and accommodates six guests so it’s the perfect place for a weekend getaway with the family.  Did we mention it also has parking?

Book now

Day 1 Pittsburgh Itinerary

Start the day off with a delicious breakfast

We hope you came hungry because Pittsburgh has a BIG food scene and there’s no better way to start the day than by going to brunch. The best brunch spot in Pittsburgh is no secret - every Pittsburgher has been here at least once. 

Pamela’s Diner in the Strip District is home to the best hotcakes in the area. You can’t pass up this iconic Pittsburgh brunch spot.

Take a stroll down Penn Avenue

The Strip District is becoming one of the hottest spots in Pittsburgh. It’s unique historic charm is juxtaposed with new and trendy businesses and living spaces. Penn Ave. along the Strip is a character in itself. Take a stroll and take in all the tchotchkes. You’ll find Steelers apparel, old-fashioned candy, coffee roasters, a fish market, people selling fresh flower bouquets, and more. There’s always something to see and experience in the Strip. 

Pay a visit to the Heinz History Museum

There’s no mistaking this building in the Strip. If you get lost on the way, just look for the big light-up Heinz Ketchup Bottle sign and it’ll guide you to your destination. 

Rent a Healthy Ride and bike along the riverfront

Pittsburgh’s bike share system has stations everywhere. Rent a bike and ride along one of the Burgh’s many trails, like this one in the Strip. The views of the Allegheny River are breathtaking (don’t get too winded, though!) and you’ll be able to take in all the iconic sites and bridges. Follow this trail and you’ll make your way to Point State Park (yes, the big water fountain).

Have a photo-op at Point State Park

This is arguably the most iconic spot in the city of Pittsburgh. The summer heat in Pittsburgh may have you sweating, especially if you’ve just biked! Luckily, Point State Park’s fountain will give you a good mist and cool-down. Plus, you can’t come to Pittsburgh and not take a photo here.

The Point is also a great place to sit and people watch. In the summer, you’ll find tons of runners, bikers, roller bladers, boaters, and jet-skiers. 

Visit the Farmers Market in Market Square

Just a short walk from the Point is Market Square, and on Saturdays from 10 a.m. to 2 p.m., it’s home to a farmers market with tons of local vendors. If you aren’t able to catch the farmers market on time, there’s still plenty to do there. Check out the activities they have set up like jumbo Janga and chess!

*There’s also free Yoga in the Square on Sundays from 10-11 a.m.!

Grab a bite to eat Downtown

There are so many options for food Downtown. Market Square has a plethora of different cuisines. Primanti Brothers offers famous Pittsburgh style sandwiches (yes, we put fries on our sandwiches here) and other fan favorites. Condado Tacos is also famous for their make-your-own taco menu and happy hour specials. 

Finish off the night with a sweet treat from Millie’s Homemade Ice Cream

Not to be dramatic, but Millie’s ice cream is to die for. Located just steps away from Market Square, they offer hand-crafted ice cream, milkshakes and floats. 

Vegans, don’t think we’ve forgotten about you. They have non-dairy flavors available, too!

Day 2 Pittsburgh Itinerary

Today’s all about the North Side. Its rich history and culture make it a must-see for every Pittsburgh visitor (we might be biased because this is where Birgo Realty was born). 

Explore Pittsburgh’s North Side and grab coffee from Commonplace Coffee

Take a morning walk through the Mexican War Streets. Here, you’ll find rich history and grandiose architecture. Then meander over to Commonplace Coffee for the best cup of joe in the Burgh. 

Visit Randyland and the Mattress Factory

Get your art on at these two must-see spots in Pittsburgh’s North Side. Randyland is an outrageous (don’t worry, in a good way!) outdoor art museum filled with brightly colored murals and objects. Sometimes the artist will even pop in to say hi.

Stroll through Allegheny Commons Park

Allegheny Commons Park boasts some of the best views of the city. Give your feet a rest on one of the benches and watch the birds take a dip in the pond. 

Bird watch at the National Aviary

Right next to Allegheny Commons Park is the National Aviary. Purchase a ticket and you’ll get to experience over 500 birds from around the world!

Drop by the Andy Warhol Museum

Yep, you can view the iconic Campbell’s Soup Can artwork and many more at the Andy Warhol Museum. It’s perfectly situated in Pittsburgh’s North Side and is just a block away from the most beautiful baseball stadium in America: PNC Park. 

Grab a drink and a bite to eat from Mike’s Beer Bar

If there’s a Pirates game going on, grab a drink from Mike’s Beer Bar and listen to the fans cheer on the Bucs. They have over 500 beers, so you’re sure to find something you like.

If you fancy actually participating in the game, the Pirates now have limited tickets available for fans to attend in-person games!

End the night on top of Mt. Washington

Did someone say #views? Before you leave the City of Bridges, you have to make a stop at Mt. Washington. The views at night are incredible and make for the perfect Insta post. If you have time, you can ride the Incline down and back!

How to Get Around Pittsburgh

Public Transportation

Navigating a new city can be hard, so why not just leave it to the experts? Jump on a Port Authority bus or the “T” and experience the city like a local. If you’re unfamiliar with public transportation, the Port Authority website has a helpful feature where you can plan your trip. It will give you all the information you need to start exploring

Another great resource to utilize while riding a PAT bus is the Moovit app. It gives real-time updates on buses and the light rail system. 


Conveniently call a ride using Uber or Lyft and be at your destination in no time. 


Healthy Ride is Pittsburgh’s bike share system. As noted before, the bikes are easily accessible with stations on nearly every street corner. Pittsburgh has many trails and bike lanes so you can have your pick between concrete jungle or real jungle. 


Luckily, Pittsburgh is a very walkable city. If you choose to go with this route, you’ll be on the top of the Fitbit leaderboard with 10,000+ steps every day.


Zip around the Burgh on a Scoobi electric scooter. Renting one costs $2.00 to unlock and $0.30 per minute after. Stations are located throughout the city and can also be found through the Scoobi app.

We’re confident our Pittsburgh weekend itinerary will give you the best the Steel City has to offer. We hope you enjoy your stay and visit back often.

Don't forget to follow our socials to stay up-to-date with the newest happenings around Pittsburgh!

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