Penn Brewery throws Pittsburgh’s longest-running Oktoberfest across the last two weekends of September 2026 — September 18–20 and September 25–27 — at the brewery on Vinial Street on the North Side. Bavarian music, German food, seasonal lagers, and the historic lagering caves underneath the building. General admission is free. Check pennbrew.com for daily hours before you go.
Pick your weekend carefully. These two weekends are not the same trip. The first, September 18–20, is the calm one. The second, September 25–27, is one of the busiest weekends of Pittsburgh’s entire year: Pitt hosts Bucknell Saturday, the Great Race runs through the city Saturday and Sunday, the Steelers host the Bengals Sunday, and IROS brings thousands of international researchers in the same Sunday. If Oktoberfest is the reason you are coming, the first weekend is the easier and cheaper book. If you want the city at full volume, take the second — and reserve early.
Why a home beats a hotel for a beer festival weekend
Nobody should be driving back from Oktoberfest. A house on the North Side means you can get there and back without a car in the equation, and it gives you a kitchen for a proper breakfast, room for the group to spread out, and somewhere to land that is not a hotel bar. For a group coming in together, one address and one kitchen beats four hotel rooms and a lobby every time.
North Side note. Our Greeves house sits on the North Side, the same side of the river as the brewery, with free on-site parking — park once for the weekend and leave the car there. Three bedrooms that each have their own private ensuite bathroom, beds for eight, and a private back deck with a BBQ grill. See Greeves for photos and dates.
Make a weekend of it
Late September is the best stretch of the Pittsburgh year, and the North Side gives you more than the brewery: the riverfront walk, the museums, and the Strip District a short hop across the river on Saturday morning. Start with our Pittsburgh food guide and Things to Do in Pittsburgh.
Where to stay. Rivers & Steel City Homes offers full homes across the Pittsburgh metropolitan area — parking, a kitchen, and room for everyone who came in. 2,700+ guests since 2018; book direct and save 5–15% over Airbnb and VRBO. Find your dates at riversandsteel.com/search.
More to plan your trip: Things to Do in Pittsburgh · Festivals on the Pittsburgh events calendar. Ready to visit? Find your stay »
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