Series: Planning for 36 Hours in Pittsburgh, PA

Planner’s Travel Series

About the series: Welcome to our ongoing travel series. These are all posts written by planning students and professionals about what to do in a given city when looking for Brunch, a Brew, or a good idea on a Budget. To cap it all off, we include a fun planning fact!

36 hours is perfect for Pittsburgh. It allows for just enough time to get a sense of the place and its idiosyncratic character but still leaves room to come back and experience more. In fact, a similar visit played a significant role in prompting my initial move to this city that I called almost-home for six years. Many are likely aware of Pittsburgh’s historic strengths as a key, resource-rich location that became a center for heavy industry, the labor movement, and wealth accumulated by the likes of Andrew Carnegie. With a more recent transition rooted in those legacies, this city that appears to organically rise from its rivers and hilly surroundings offers endless options for brunch, brew, and activities on a budget.


If this is your first visit to Pittsburgh, P&G’s Pamela’s Diner is a must. Although Pamela’s does offer lunch, stick with the breakfast menu. Try the crepe-style “hotcakes” that the Obamas served at the White House after a campaign visit, or get the Tex-Mex omelet that comes with a side of their “famous” Lyonnaise potatoes. The Strip District location gets particularly busy, but visit early or on a weekday and see the city’s traditional market district in action after. There is a particularly nice historic Polish church across the street (immigrants from Eastern and Southern Europe once settled much of the region), and Prestogeorge and La Prima Espresso are both great places to grab a cup of coffee while walking around the neighborhood.

Squirrel Hill Cafe. Photo Credit: Joseph Hoffheimer.


Pittsburgh is a quintessential beer town. While longstanding Iron City invented the pull-tab, and scores of other breweries have opened in recent years, this city truly excels in its diversity of neighborhood dive bars. Two of the best to experience both old and new are the Squirrel Hill Cafe and Park House. The Squirrel Hill Café, affectionately known as the Cage, is frequented by everyone from neighborhood regulars to grad students. It has a classic smoky vibe but with local East End beer (along with cheap PBR, of course) and a surprisingly good-but-basic bar food menu (get the burger or cheese balls). Anthony Bourdain once spent hours here; it was his type of place. As a non-smoky alternative, hit the Park House on a night with music, often bluegrass and always free (as are the peanuts and popcorn). The oldest bar in the city, the Park House has a timeless feel, though it has been recently updated, with local craft brews and Israeli-style falafel. If you still feel the need to visit a brewery, cross the Monongahela River to Voodoo’s Homestead location, an employee-owned taproom that has adaptively reused a historic firehouse in a part of the area known for its pivotal role in the steel industry and labor movement.


South Side Slopes. Photo Credit: Joseph Hoffheimer.

Budget Activity

Pittsburgh may not be as cheap as it was, but the breathtaking views never change in this topographically-unique city. For first-time visitors, Mount Washington is a must, and two funiculars, the Monongahela and Duquesne Inclines, offer an easy way to get there for the price of a bus fare. As an alternative, visit the South Side Slopes and climb the public staircases that function as “paper streets” on hillsides too steep for regular thoroughfares. You will get a great workout, experience less conventional views, and afterwards can explore the South Side Flats, one of the longest Victorian-era business districts (and stretches of bars) in the country.

Fun Planning Fact

In this grid-less city of three rivers and ninety official neighborhoods that took its present form from annexing Allegheny City (after Brooklyn, the second largest in the U. S. to ever cease existence), this place abounds with planning facts. Unfortunate ones include the urban renewal that created Point State Park, serving as the source of the Ohio River but also nearly destroyed several neighborhoods. The Hill District, once one of the country’s most vibrant African-American neighborhoods, spawned notable jazz legends, baseball Hall of Famers, and playwright August Wilson.

Pittsburgh Bridges. Photo Credit: Joseph Hoffheimer.


For a more fun fact, the one that sticks with me the most after leaving involves Pittsburgh’s landmark bridges, which at 446, outnumber Venice. In one of the country’s steepest cities, some crossings, such as the Bloomfield, merely bridge deep ravines. More notably, Pittsburgh’s 26 major river bridges take a variety of forms: many are painted yellow; the bike-friendly Smithfield Street Bridge that once carried streetcars served as a prototype for major spans in New York City; and a dedicated portion of the restored Hot Metal Bridge has been converted into bicycle and pedestrian use.

Featured Image: Night view of Pittsburgh from Mt. Washington. Photo Credit: Joseph Hoffheimer. 

About the Author: Joseph Hoffheimer is a second year graduate student in the Department of City and Regional Planning at UNC Chapel Hill and is specializing in economic development. He is an avid music and travel enthusiast, and spent 6 years in Pittsburgh.