Date Nights in Pittsburgh

Romance is in the air all year long in the Cultural District. Whether you're planning a first date or a special anniversary, check out these date night ideas in Downtown Pittsburgh!

Catch a Show

The old-world glamour of the Benedum Center and Heinz Hall to the sleek modern appeal of the O’Reilly Theater and August Wilson Center, the Cultural District brings innovative and exciting entertainment to Pittsburgh almost every night of the year. Check out the fall calendar to see what’s on stage in the Cultural District this season. Catch a performance of the holiday classic, The Nutcracker (November 30-December 27, Benedum Center), sample holiday wines and toast to the season at our final Wednesday Wine Flight (December 5, Greer Cabaret Theater) of the year, or enjoy the smooth harmonies of Straight No Chaser (December 5-6, Benedum Center).

Dance The Night Away at the Cabaret

Every Friday, the Cultural District heats up with salsa dancing at the Cabaret at Theater Square, and you can spend a late night twirling your partner around the dance floor. Lean in to the Caribbean vibe by grabbing dinner and drinks at Pirata on Forbes, or enjoy a happy hour at Backstage Bar, which sits adjacent to the Cabaret, from 9pm-11pm. Late night admission is free to ticket holders of any earlier Cultural District show, or $5 at the door.

a couple salsa dances together on a date night in Pittsburgh

Cozy Up With Coffee & Conversation

With the right ambience, low-key coffee dates can be just as romantic as extravagant dinners. Fort Pitt Coffee’s (1 Market Street) winter white fireplace and exposed brick walls create a cozy vibe to steal some time with your sweetheart, but the upstairs of Rock’n’Joe (524 Penn Avenue) is also a quiet and inviting space for a midday break.

Chill at Backstage Bar

With an entrance nestled in the far back corner of Katz Plaza, Backstage Bar manages to feel far removed from the bustle of the Cultural District while placing you in the heart of it all. Spend an intimate date night enjoying a delicious menu crafted by Richard DeShantz Restaurant Group (Meat & Potatoes, Butcher and the Rye) and toasting your relationship with a specialty cocktail. Plus, you can treat your date to free live music at Backstage Bar three nights a week: on Tuesdays, check out our BNY Mellon Presents JazzLive Series, and on Fridays and Saturdays, stop by to see House Band Daryl Shawn or a rotating lineup of guitarists, pianists, and jazz artists.

a couple enjoys drinks together on a Pittsburgh date night at Backstage Bar

Roar with Laughter at Arcade Comedy Theater

For a more playful couple, Arcade Comedy Theater is just the spot to keep you both laughing all evening long. Now in its new home at 943 Liberty Avenue, Arcade Comedy Theater’s lineup includes hilarious shows like Your Life: The Musical and Dinner With The Nolens. Grab your favorite bottle of wine or six pack to enjoy while you watch. Truly adventurous couples can plan a unique date where they learn the art of comedy together during one of Arcade Academy's classes and workshops.

Warm Up With a Whiskey Tour

Pittsburgh is the birthplace of American whiskey, and it’s enjoying a spirited revival in the city it calls home. Warm up with your partner this winter by going on a whiskey tour of Downtown. A perfect starting place is the Omni William Penn Hotel, which is home to both a Wigle Whiskey’s Tasting Room and a basement level Speakeasy.

From there, you’re a short walk from several Cultural District bars with excellent whiskey selections, including Butcher and the Rye (212 6th Street) and Braddock’s American Brasserie (107 6th Street).