Fall and Winter Dates in the Cultural District

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

From the old-world glamour of the Benedum Center and Heinz Hall to the sleek modern appeal of the O’Reilly Theater and Liberty Magic, the Cultural District brings innovative and exciting entertainment to Pittsburgh almost every night of the year. Check out the fall and winter calendar to see what’s on stage in the Cultural District this season.

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. 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.

Create Your Own Gallery Crawl

You don’t have to wait for the next Gallery Crawl to roam the exhibitions hand in hand with your sweetheart. Our galleries are free and open to the public Wednesday to Sunday, allowing you to interpret art and take Instagram-worthy photos together anytime you want. Take a break from the hustle and bustle at the new Trust Oasis, a pop-up arts experience featuring the return of the Los Trompos spinning tops, then head around the corner to Boat Trip at Wood Street Galleries. End your evening with a stop at SPACE Gallery to check out Mutant Media.

Cozy Up With Coffee & Conversation

With the right ambiance, 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 the delicious menu 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.