Swift, a 10-time Grammy winner, thrilled the crowd as she performed an acoustic version of her hit “Shake it Off.”
"Modern Family" star Jesse Tyler Ferguson, who was the headliner for a celebration of the 50th anniversary of the Stonewall Uprising, joined Swift on stage for a duet.
The invitation-only event was co-hosted by Diva Jackie Dupree and included billed performances by Sara Bareilles, Gavin Creel, Lea DeLaria, VINCINT and more.
AEG, the entertainment company that represents Swift, presented the show and a check for $50,000 to the Stonewall Inn's charity initiative.
The Stonewall Uprising, in 1969, is credited as a catalyst for the gay rights movement when the New York Police Department busted into the establishment and tried to arrest anyone who was cross-dressing -- which was illegal at the time -- and seize alcohol at the unlicensed bar.
This is not the first time Swift stunned the LGBTQ community. In April, she donated $113,000 to the Tennessee Equality Project, an LGBT advocacy group in the singer's home state.
T.E.P.'s executive director, Chris Sanders, said in a statement at the time that the organization was "honored and grateful" for her gift, adding, "Taylor Swift has been a long-time ally to the LGBTQ community."
She also specifically endorsed Democrat Phil Bredesen in Tennessee's Senate race last year because of Republican Marsha Blackburn's lack of support for gay rights. Blackburn, however, went on to win the seat.
The pop star recently dropped a new song, “You Need to Calm Down,” from her upcoming album, "Lover."
The video for the new single will debut on ABC’s "Good Morning America” on Monday.