Romantic 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, Byham Theater, 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 May calendar to see what’s on stage in the Cultural District this month. Our top picks for a romantic date night in Pittsburgh are Pittsburgh Ballet Theatre's West Side Story Suite, In The Night, and Fancy Free May 4-6 at the Benedum Center; Pittsburgh Symphony Orchestra's Love, Lust & Rock 'n' Roll May 11-13 at Heinz Hall, and Roger + Hammerstein's Cinderella May 22-27 at Heinz Hall.

a young couple stare lovingly into each others eyes

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

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 advantage of the spring weather with a stop at Tony Tasset's colorful Magnolias for Pittsburgh installation on the corner of 7th and Penn, then head around the corner to Kara Skylling's You Will Arrive exhibit at 707 Penn Gallery. End your evening with a stop at Wood Street Galleries to check out Macular's latest kinetic light installations, Cycles.

a couple enjoys a work of art together at a gallery in Pittsburgh

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 Serieszbfwbautwxqdqctvawybyzyexsa, 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.