Behind the scenes at Oktoberfest: What it’s really like to host Pittsburgh’s biggest fall fest

There’s sausage, lederhosen, beer in milk jugs … and just a little bit of stress.

It's time.

It's time.

Chris Togneri / For The Incline

It’s that time of year again, when Sandy Cindrich wakes up at night to worry about things both beyond her control, like the weather, and within her control, including tent rentals, band rosters, the 25-or-so additional hires needed to pull off this event and, of course, whether or not they have enough milk cartons.

“It is fun,” said Cindrich, CEO of Penn Brewery, which will host the city’s largest annual Oktoberfest celebration this month. “But it’s one of those things … our office manager, Lisa, has been with us three years, and the first year she was so gung-ho and ready to go and full of enthusiasm. And I said, ‘Well, we used to be like that, too.’”

Don’t get Cindrich wrong.

It’s a great time, to be sure. But I live in Troy Hill, just up the street from the stately brick complex, so I know firsthand what Penn Brewery’s Oktoberfest means.

And it’s nuts.

Every year, Oktoberfest temporarily transforms Penn Brewery’s little corner of the North Side, at the base of Troy Hill, into a massive sausage-, beer- and lederhosen-fueled party.

Penn Brewery is the city’s original craft brewery, which opened in 1986 with an emphasis on German-style lagers, and it draws 8,000 to 10,000 people over the six-day event. The brewery’s Oktoberfest celebration is the biggest in town, so we took an inside look at what it’s like to plan this massive fall fest, and we’ll share some pro tips if you’re heading there. We’ve got a few other Pittsburgh Oktoberfest recommendations, too. Prost!

Chris Togneri / For The Incline

Penn Brewery

Sept. 15-17 and 22-24

Troy Hill Road becomes a parking lot, from the trail parking at the base of the street all the way up to Provident Charter School (the former North Catholic High School) half-a-mile up the hill. Penn Brewery pays the city for three police officers to direct traffic, discourage excessive rowdiness and ensure that nobody takes beer off premises. Each day starts as family-friendly while the sun is out, then turns into raucous shoulder-to-shoulder partying come nightfall.

“It’s a lot of work, but I always enjoy making my way through the tents and seeing all the people enjoying themselves,” Cindrich said. “Yeah, I’m losing sleep now, but when you get to that point, and all the hard work is done, it is so worth it. To us, this is a big deal. It’s the biggest Oktoberfest event in the city, and we take so much pride in that.”

Plus, Penn Brewery’s Oktoberfest is your chance to drink beer from a milk carton, and who doesn’t want to do that, amiright?

“It’s one of those things we’ve been doing for a long time, before we took over ownership” from Tom Pastorius, the original owner, Cindrich said. “It’s a tradition and people really like it. They say, ‘you’re going to have the milk cartons again, right?’ Yes, we will. Because it is totally acceptable to drink beer out of a milk jug.”



Now a parking lot, soon-to-be a party lot.

Chris Togneri / For The Incline

Head brewer Nick Rosich has been busy brewing more than 200 half barrels of Penn Brewery’s most popular seasonal beer, Oktoberfest. I caught up with Rosich last week, at Hitchhiker Brewing Co.’s soft opening of its new Sharpsburg facility (we’ve got more on Hitchhiker here), to talk about the beer, a light-colored, balanced, malty lager with IBU rating in the 25 to 27 range.

“It’s as an easy drinker,” Rosich said. “Low bitterness, malty but perfectly balanced. Not a big beer, but bigger than your average German lager.”

If that sounds like something you want to try, we offer a few words to the wise.

Pro tips from a Penn Brewery Oktoberfest veteran:


Street parking is limited and fills up quickly. Other options include The Sarah Heinz House parking lot (except Sundays) and Provident Charter School parking lot. Penn Brewery officials suggest Uber/Lfyt as an alternative to driving.


Bring it. Unless you’re in the restaurant, cards are not accepted. Multiple ATMs will be on site.


The kitchen will serve seasonal German favorites, and outdoor tents will offer dishes including Sauerbraten and Rouladen.


Live bands will perform traditional German music inside and out every day.

Teutonia Männerchor

Through Sept. 10

Just down the street in Deutschtown, Teutonia Männerchor is in the middle of its Oktoberfest, which started Friday and ends this evening, Sept. 10. If you can make it out there today, look for the big tent at 847 Phineas Street and expect live music and dancing at this German singing society founded in 1854.

The Independent Brewing Co.

Sept. 19—30

In Squirrel Hill, The Independent Brewing Co., which typically sells only locally made beers, will make several exceptions this month for traditional beers imported from Germany, including some that have likely never been poured in western Pennsylvania.

Here’s the list, with descriptions from the Independent’s co-owner Pete Kurzweg:

  • 1809 Berliner: A tough-to-find, traditional, dual-culture Berliner weisse brewed by legendary Bavarian brewmeister Dr. Fritz Briem at Weihenstephaner brewery.
  • Einbecker Mai-Ur-Bock: A traditional Maibock.
  • Uerige Doppelsticke: A stronger take on the classic Dusseldorf altbier.
  • Schlenkerla Märzen: A big, bad smoked märzen that transports you immediately to a campfire on a crisp autumn evening.
  • Weihenstephaner Krystalweiss: Very similar to Weihenstephaner’s acclaimed Hefeweizen but filtered for startling clarity.
  • Schneider Weisse: A unique, amber-hued hefeweizen that lends caramel from its middle malts to add to the traditional clove and banana tastes and aromas from the yeast. (We purchased this one at the special request of Roundabout owner/brewer Steve Sloan, who brews a beautiful take on this beer called “Ferdl Weiss”).
  • Ayinger Oktoberfest: A perfectly-executed traditional märzen.
  • Reissdorf Kölsch: The gold standard of kölsch, the cold-fermented ale that defines a night out in Cologne.

“Hop-heads need not fear, however, as the bar will devote the remaining half of its taps to a selection of locally-brewed, hop-forward ales,” Kurzweg added.

Um … why is Oktoberfest in September anyway?

No matter which fest you choose, you might be wondering … why isn’t this holiday in its namesake month?

The answer, it turns out, involves something that is keeping Penn Brewery’s Cindrich awake at night: The weather. It just tends to be nicer out in September than in October, so even brewmasters in Munich have over the years moved Oktoberfest to the last two weekends of September.

Still doesn’t cut down on the stress at Penn Brewery.

“I think a lot of our team is made up of people who can feed off anxiety and turn it into power,” Rosich said. “So is it more stressful or fun? A little bit of both.”