Weekend Trip to Pittsburgh:

An Itinerary

As a resident of Pittsburgh, I would like to take you on a trip that avoids almost every “tourist” attraction in the city. I love my hometown, and living away from Pittsburgh for a while simply made me love it even more when I returned. So let me guide you through all of the little things that make Pittsburgh unique and places that you won’t find in any other city.


Photo: Michael Fornataro


Point State Park/Downtown/The Strip/Lawrenceville


Friday’s itinerary will take you in an arc around the city, starting at the Pointe and working all the way around to Station Square and the Grandview Overlook. So, let’s start at the beginning of the day: breakfast!

If you find yourself near the Strip District in the morning and are craving traditional breakfast food from a “greasy spoon” diner, then you’ll want to try Pamela’s.

After breakfast, hike the North Shore Riverfront Trail and dip your feet in the fountain at Point State Park. This is a great start to a beautiful city view–and you’ll understand why it’s referred to as “the Golden Triangle”–along with the splendor of the Allegheny River and the Monongahela River intersecting to become the Ohio River. You will also have a great view of plenty of our well-traveled bridges–hence the nickname “city of bridges.” 446 bridges, to answer your question!

You can also rent a kayak and take to the water, passing by the boats from the Gateway Clipper Fleet as you do so.

If you make the trek further down the North Shore along the Three Rivers Heritage Trail until you get to the David L. Lawrence Convention Center, you can duck under the building to see the waterfall stairs, a hidden staircase below street level that cuts right through a waterfall on either side (see photo below)! They are a spectacular hidden gem in the middle of the city!



If you want to try an eatery that is exclusive to Pittsburgh, look no further than Primanti Bros. in the Strip for lunch! There are several locations around the city, but the one in the Strip District is the original restaurant that launched in 1933! Primanti’s is known for its extensive sandwich menu, but each sandwich is stacked high with french fries and coleslaw, a staple in all of the restaurants.



After lunch, definitely walk the Strip, an outdoor marketplace stretching roughly 22 city blocks right along the Allegheny river. You can do some shopping, people watch, and take in the different outdoor vendors.  If you want to learn more about the local culturel, visit the Heinz History Center or the Andy Warhol Museum. Both are peaceful and educational as you explore each floor!

Fun Fact: Some local lore about Heinz History Center–some say the museum is haunted!


After all that walking and then museum perusing, it’s time to migrate towards the Lawrenceville neighborhood of the city, a bit further East from where we began. I recently stumbled upon a fun little burger joint called Burgh’ers. This restaurant has burgers uniquely named for the specific neighborhood or region of the city they represent. For example: the Pittsburgher, the Polish Hill, the Lawrenceville, and the Shadyside to name just a few.

If you are still feeling adventurous after dinner, do some window shopping along Butler street, and enjoy some of the bars and nightlife before you turn in for the evening.





Pick up where you left off in the neighborhood of Bloomfield, directly bordering Lawrenceville and Shadyside. If you liked breakfast at Pamela’s, then you’ll love stopping by Ritter’s Diner in Bloomfield!

After breakfast, make your way to Schenley Park and take a stroll on one of the trials before it’s time for lunch. If you’re not in the mood to walk outside, duck into the Carnegie Museum of Natural History and take in the dinosaur bones and other exhibits.

Fun Fact: For any movie junkies, a few scenes from the Silence of the Lambs were shot in this very museum along with other destinations around Pittsburgh!


By now, you’ll have made your way further into Oakland and seen the busy, bustling sidewalks filled with students and young professionals from several different universities. Amidst all the sights, don’t pass up a hidden gem of an eatery, Conflict Kitchen, for lunch. This restaurant is unique as it serves cuisine from regions of the world with which the United States is currently in conflict.

While you’re there, check out the breathtaking architecture of the Cathedral of Learning, a hard to miss building on the University of Pittsburgh campus, as it’s 42-stories tall!



If you see a domed greenhouse in the distance, buy a day’s admission to Phipps Conservatory and Botanical Gardens. There are stunning seasonal flower shows and 15 acres of greenery to experience!


As the day winds down, make your way into the Shadyside neighborhood to hit up a few locally-owned shops before grabbing dinner at the Church Brew Works on Liberty Avenue in Bloomfield. This restaurant is inside a restored Roman Catholic church–the building itself is over a century old!


Southside Works/Carson Street/Station Square/Mt. Washington


For your final breakfast in the city, try something a little different and hit up Waffles Incaffeinated on Carson Street in the South Side. Not a waffles fan? There are several other breakfast joints on the 21-block stretch of East Carson Street. I recommend O’Leary’s Restaurant for some great breakfast food before you depart!

Enjoy the morning and do some window shopping and also people watching in this part of the city!



One of the last things you should do before having a goodbye lunch is taking a ride on the Duquesne Incline. This tiny car ride will slowly ascend to the top of Mt. Washington and give you a great view of the city from every angle!

If you’re in the mood for something fancy, at the top of Mt. Washington, enjoy a small lunch at Le Mont–a restaurant with a panoramic view of the city. I also highly recommend stopping by the Grandview Overlook for some great photos before saying see ya later!



Have you been to Pittsburgh? What were your favorite spots to visit? Let us know, and don’t forget to Pin it!

Postcard Press: Planning a trip to Pittsburgh? Jax has your trip covered in this awesome itinerary! #travelblog #travelUSA #pittsburgh

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