Penn Brewery’s Oktoberfest on the North Side — Bavarian music, German food, seasonal lagers and the brewery’s historic lagering caves. Free general admission. Check pennbrew.com for daily hours.

Read the full guide → Penn Brewery Oktoberfest: where to stay

Penn Brewery’s Oktoberfest on the North Side — Bavarian music, German food, seasonal lagers and the brewery’s historic lagering caves. Free general admission. Check pennbrew.com for daily hours.

Read the full guide → Penn Brewery Oktoberfest: where to stay

The 45th annual Three Rivers Film Festival screens across multiple Pittsburgh venues over ten days. Book your stay near the action →

Read the full guide → Three Rivers Film Festival: where to stay for the ten-day run

Pittsburgh’s holiday kickoff lights up the Cultural District. (2026 date to be confirmed.) Book your stay near the action →

Ring in 2027 at Highmark First Night, Pittsburgh’s family-friendly New Year’s Eve celebration in the Cultural District. Book your stay near the action →