Weekend in Pittsburgh: A Gentleman’s Guide to the Best Things to Eat, Drink, and Enjoy from Our Local Insider

weekend in pittsburgh travel guide

If you're like us, when you travel you like to do the same things you love doing at home but in an interesting new place:

People watching over great coffee, living like a local, browsing cool men's stores, eating at delicious regional restaurants, grabbing a great cocktail or two, and then the city's best slice of pizza on the way back to the hotel.

Primer Contributor Nick Guzan shares his local Pittsburgh favorites when you drop into town with a carryon.

Is Pittsburgh the new Austin? From steel town to tech hub.

New York, Los Angeles, Chicago, Boston, and Miami are the obvious cities that come to mind when considering examples of the United States’ bustling culture and vibrant nightlife. For decades, it’s no surprise to hear about new restaurants and cocktail spots or exciting brands and venues out of these most populous of American cities. As the 21st century sees a rise of a new American renaissance, Primer is shining a spotlight on the world class spots in these less populated but exciting cities, beginning with Pittsburgh, Pennsylvania.

Butcher and the rye pittsburgh cocktails
Butcher and the Rye | Pittsburgh Magazine

Amazon Almost Went to Pittsburgh … That Says A Lot

Pittsburgh’s spot as one of 20 contenders to advance to the second level of consideration for Amazon’s HQ2 is indicative of its half-century of progress since smoke and fumes from the city’s signature steel industry darkened the skies over southwestern Pennsylvania.

Once referred to as “Hell with the lid off,” Pittsburgh responded to its record-setting air pollution levels generated during World War II with waves of renewal initiatives that cleaned the air and the city’s signature three rivers as its economic focus shifted to banking, technology, and education.

What to Check Out in Pittsburgh

The city still earns its reputation as an industrial hub, but Pittsburgh is now making its mark with innovations in the tech, healthcare, and dining industries, frequently making the top of lists ranking America’s most livable cities.

Samuel Baron Clothiers

Best Men’s Clothier:

Samuel Baron

Once upon a time, “dressing up” in Pittsburgh seemed to mean wearing khakis rather than jeans with your Steelers jersey.

Now, with the help of talented indie tailor shops like Samuel Baron Clothiers in Shadyside, gentlemen in the ‘Burgh are dressing better. And speaking of Steelers… wide receiver Hines Ward has been a bespoke-wearing Samuel Baron client since 2014.

Best Distillery:


Wigle pays homage to the city’s revolutionary past while paving the way for its future with a bustling distillery that has increased its initial rye and wheat-based whiskey offerings to include Pennsylvania Bourbon, bitters, gin, and even “Landlocked” rum, all available for sale and sample during Wigle’s fabulous garden parties.

pittsburgh best distillery

Pittsburgh Beautiful


The distillery was named for Philip Wigle, a proud Western Pennsylvania rebel who was sentenced to hang for his role in the region’s infamous Whiskey Rebellion in 1794. (He was ultimately pardoned by George Washington himself!)

The distillery bearing his name began operations in Pittsburgh’s Strip District neighborhood in December 2011.

Best Brewery:

Penn Brewery

Pittsburgh was one of the breeding grounds of the craft beer movement with the opening of Penn Brewery in 1986 in the city’s historic North Side, among the first of the more than 30 craft breweries currently operating in Pittsburgh.

best distillery in pittsburgh penn brewery

More than three decades after it opened its doors, Penn Brewery continues to expand its award-winning lineup, adding IPAs and chocolate stouts to its authentic original selections made with real German hops and two-row barley.}

best cocktail spot pittsburgh

Best Cocktail Spot:

Hidden Harbor

Hidden Harbor is my go-to for dates, hosting out-of-towners, or just needing a spot to try something fun. It's a tiki bar that sheds the tacky connotation by embracing it head-on, offering a constantly innovating menu and an unpretentious, knowledgeable staff. I’ve never had a bad time or, perhaps more importantly, a bad drink there.

Of course, Pittsburgh hasn’t lost sight of its origins as a shot-and-a-beer town and neighborhood bars like Gene’s Place, Kelly’s Bar & Lounge, The Modern Café, and the Squirrel Hill Café (aka “The Cage”) serve up cheap beer and delicious greasy eats perfect for watching a Penguins game or ending your night on a good note.

Specifically, if you're looking for a great Old Fashioned, Primer readers nominated Butcher and the Rye in our guide to the best Old Fashioneds in 47 cities.

Best Coffee:

Commonplace Coffee

Commonplace Coffee is my favorite of the bustling coffee scene in the burgh… though my sister would argue for Coffee Tree Roasters.

best coffeeship in pittsburgh
commonplace coffee
primanti bros

Best Local Eats:

Primanti Brothers + A Ton of New Places

Pittsburgh tradition would send newcomers to salt-of-the-earth (and plenty of salt in general) classics like Primanti Brothers (above) or Oakland’s Original Hot Dog Shop, but the city has evolved far from its fries-on-sandwiches roots with exciting cuisine at Bar Marco, The Commoner at Hotel Monaco, DiAnoia's, The Independent (Hidden Harbor's partnering gastropub), Meat and Potatoes, Noodlehead, Paris 66, Proper, Smoke, Spoon, tako and Whitfield at Ace Hotel … to name a few.


Best Pittsburgh Pizza:

Aiello's Pizza and Mineo's Pizza House

Second only to Miami as far as pizza per capita, one of Pittsburgh’s most fevered internal rivalries comes down to a single block on Murray Avenue in Squirrel Hill where diners must choose between Aiello’s Pizza (since 1978) or Mineo’s Pizza House (since 1958). Your best bet: get a slice of your favorite from each one and see what you prefer.

Must-see Local Attractions:

Row House Cinema and Randyland

Row House Cinema in Lawrenceville shows classics during its ingeniously themed weeks, brings in beer from Bierport next door, and has the best popcorn I've ever tasted.

row house cinema

Pittsburgh City Paper

A group of colorful flowers in a garden

Photo by Triphobo

If you’re literally looking for local color (and yes, I do mean literally), Randyland is a must. Plus, it’s right on the North Side by the Mattress Factory, a contemporary art museum, and another must-stop place on your visit to Pittsburgh.

Do you have a favorite spot you visited in Pittsburgh? Keep the guide going in the comments!

This post may contain affiliate links, read about our editorial promise
Nick Guzan

Nick Guzan is a public relations consultant and writer living in Pittsburgh. He blogs about men's style in movies and TV at BAMFStyle.com. His interests include old movies, muscle cars, maritime disasters, fast food, and single malt Scotch.