A 5-Mile Walking Tour of Pittsburgh to See 17 Unique Highlights

When we visit cities around the world as travelers, one of the first things we do is figure out a grand walking tour in order to get a feel for the city. We generally take anywhere from a half-day or full-day to do these self-guided city tours and really love checking things out on foot.

Until now, we had never put together one of these guides for Pittsburgh as our 90 neighborhoods often make it difficult to get around and see them all. Still, the neighborhoods in and around the central business district in downtown Pittsburgh have quite a lot to see and many of these spots are on the radar of those visiting Pittsburgh for the first time as well as long-time residents.

So in this one, we wanted to share what we consider to be the ultimate walking tour of downtown Pittsburgh! This walking tour covers five miles in the North Side, downtown Pittsburgh, Mount Washington, and Station Square and has 17 unique highlights worth checking out. 

So put your walking shoes on and get to exploring this beautiful city!

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Bonfire Review – A Wood-Fired Oven in the First Floor Restaurant

Bonfire is a two-story restaurant concept in South Side by Chef Chris Bonfili, former chef of the now-closed Avenue B restaurant. While the South Side neighborhood may not have historically been on anyone's radar as a dining destination, restaurants like Bonfire are helping to slowly change that.

At Bonfire, you can dine in the more formal upstairs space with dishes like mussels, blistered shishito peppers, arctic char, and strip steak. Or, you can relax in the more casual space downstairs with options like flatbreads, mac and cheese, and sandwiches. Either way, the menus are a far cry from the bar food typical of this neighborhood.

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An Attraction, Drinking, and Eating Guide to Pittsburgh’s South Side

Pittsburgh's South Side is often known as its bar crawl neighborhood, and you do not need to spend much time exploring this one to understand why that is- the bars are everywhere.

While this one is incredibly popular for college kids looking for a cheap drink and anyone in need of a night out with libations, there is actually quite a bit going on in the neighborhood beyond your typical bar. For us, while we visit this one for a periodic adult beverage ourselves, we often visit for other reasons, and wanted to highlight some of our favorite attractions, restaurants, and of course, bars in this neighborhood guide!

It is worth noting that the following is not a collection of every business in South Side. This article only features businesses that we personally visit when we explore the neighborhood. As such, it should only be taken as a starting point and is certainly not a list of every establishment. If you see an interesting business while exploring the South Side, do yourself a favor and go inside!

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The Library Review – A South Side Gem for Cheap Eats and Drinks

Sometimes when we try and find a new bar to hit in South Side, we go numb at the sheer number of choices. In many cases when visiting this neighborhood we often pick a reason for going out (deals, cocktails, draft list, etc.) and then limit our options down from there in order to make a choice.

On a recent night out we wanted to keep our tab low while having good beer and settled on The Library. Known for a cheap craft beer list and happy hour food specials, an affordable outing was exactly what we got!

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Cocktails from the Crypt Review – Halloween Themed Libations

Pittsburgh's Halloween season is in full force with a number of hauntingly fun attractions to enjoy. Naturally, some pop-up bars have jumped onto the scene to celebrate this spooky season with themed libations!

One of these themed bars is Cocktails from the Crypt, a South Side pop-up managed by Spencer Warren of The Warren (a popular cocktail bar in downtown Pittsburgh).

I checked this one out shortly after it opened for its limited run and share a bit more on what the bar and cocktails are like below! 

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Dish Osteria Review – An Italian Gem in South Side

Dish Osteria in South Side is a cozy, traditional Italian restaurant that initially opened way back in 2000. While we had never made a visit before they closed in 2017, the spot had long been on our list of places to try. When they re-opened in the spring of 2019 we knew we had to make it a priority to hit up this much-loved Pittsburgh institution.

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South Side Traveler’s Rest Review – Finally, A True Pittsburgh Hostel

As avid travelers, we've done our fair share of overnight stays in hostels- from $3 hole-in-the-walls in central China to high-end lodge-esque accommodations dedicated to hikers in Patagonia. Whenever we need to travel economically, we look toward shared dorms and private rooms at hostels in order to meet our travel goals.

One thing that always bothered me about the Pittsburgh hotel scene is that we never had a hostel to call our own- until now.

South Side Traveler's Rest is what we would call the first true Pittsburgh hostel, and all we have to say is its about time! 

I recently was invited to the hostel for an overnight stay and wanted to share a bit more about this hidden gem in the South Side.

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Cambod-Ican Kitchen Review – Go for the Cambodian Staples

If you find yourself in South Side and are looking for dinner, or a late night snack, or a late late night snack, a visit to Cambod-Ican Kitchen may be for you. This particular spot serves staples from Cambodia from 6pm until 3 or 4 am!

So if you are in the mood for a different kind of Asian fare, you may want to try this one out!

During my first visit I opted for a Cambodian classic which hit the spot!

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The Colombian Spot Review – Go for the Arepas

The Colombian Spot is a casual restaurant in the South Side with a menu full of authentic Colombian dishes like arepas, empanadas, ropa vieja, tostones, and bandeja paisa.

There aren't too many places in Pittsburgh where you can find Colombian food, which is why we're super happy that The Colombian Spot exists and is delicious to boot.

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