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

Note: The Clemente Bridge is currently closed for rehabilitation. Those who take this walk will need to cross on the Warhol Bridge one block to the east. Likewise, from August to approximately December 2022 (TBD) the Monongahela Incline will be closed, so we recommend avoiding the Incline segments on this route until the Incline re-opens. This is listed as our optional detour just before the Duquesne Incline section of this article.

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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Emerson’s Bar Review – A Cozy Space for Drinks in Downtown Pittsburgh

Emerson's Bar first started as a Christmas pop-up bar above Market Street Grocery in downtown Pittsburgh in late 2019, and was converted into a permanent bar space in early 2020 with a large and inviting space and a relatively straight forward bar menu.

So if you're in need of a cozy space to enjoy a drink with friends in downtown Pittsburgh, you may want to give this one a try!

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Kimpton Hotel Monaco Review – Modern Comforts and Dog Friendly Space

The Kimpton Hotel Monaco in downtown Pittsburgh is often considered to be one of the best value options in the city, but it wasn't until we stayed overnight that we started to understand why that is.

Yes, this one has relatively affordable rooms downtown, but it also backs it up with a high quality stay all around. So after visiting this one for a weekend stay, well, call us fans!

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Omni William Penn Hotel Review – A Historical Ambiance

I was eagerly anticipating my visit to the Omni William Penn Hotel in downtown Pittsburgh as this historic hotel is perhaps the most iconic of any in the city. One step in the lobby and you feel transported to a different time.

But sadly, this does not translate over into the room nearly as much, and I have to say- I was fairly let down from my stay here.

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How to Get The Most Out of First Night in Pittsburgh

Pittsburgh's First Night is an annual New Year's Eve celebration in the Cultural District that features late-night gallery hours, live music, performances at many venues, food trucks, and so much more.

While this one is a ticketed event for a nominal fee ($10 plus fees in 2019 but will be free in 2021), there really is a lot to see and experience in this one. 

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Sly Fox Brewing Review – Taphouse and Restaurant Near The Point

Sly Fox Brewing is a popular craft brewery that has been making beer outside of Philadelphia since the mid-90s. But it wasn't until 2019 that this one expanded into Pittsburgh with a taproom just steps away from Point State Park

As we believe that downtown is in need of more places for good, craft beer, we were eager to check this one out shortly after it opened to try their beer and housemade pizza. Sadly, we left this one fairly disappointed.

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Celebrating All Things Pickle at the Picklesburgh Festival

Note: In 2022, Picklesburgh was relocated to the Rachel Carson Bridge and the 10th Street Bypass.

If there should be an award for a festival that has come the furthest in recent years, it would most certainly be Picklesburgh.

When the event first started in 2015, we were underwhelmed. The Clemente Bridge was crowded shoulder-to-shoulder with patrons, and the number of vendors with pickle themed products was, well, few and far between. Apart from the gigantic pickle floating over the bridge, we did not got any pickle love at all.

We tried to return to this one a few years in the past, but had trouble finding parking and bailed. It wasn't until the 2019 edition of the festival (its 5th year) that we finally made it back, right after the festival was selected as the top specialty food festival in USA Today's 10Best contest, and we can safely say this one has made it to become a stellar event.

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Bridges & Bourbon Review – Elevating Pittsburgh’s Craft Cocktail Scene

Bridges & Bourbon opened in Pittsburgh's Cultural District in June 2019 and was a much-awaited cocktail bar due to their strong lead-up on social media.

The bar focuses on high-end cocktails with some rather interesting flair and novelties thrown into the mix as well, making it rather unique in Pittsburgh's cocktail bar scene!

We were guests of Bridges & Bourbon for a media preview event and wanted to share some of the great cocktails we tried in this one!

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Being Transported to the Amalfi Coast at Vallozzi’s Festa di Limoncello

The kickoff of summer in Pittsburgh is marked by many events, be it through the traditional solstice or simply numerous outdoor experiences.

One relatively new event is a smaller one, but focuses on all things limoncello and ‘cello spirits at Vallozzi's. This is the Festa di Limoncello, and is designed to kick off summer with a trip to the Amalfi coast of Italy.

We were guest of Vallozzi's for this one in 2019, and share what the event is like below!

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