Multi-Talented Singer-Songwriter Ryan Cassata Will Serve As Grand Marshal, Lead Entertainer for 2026 Annapolis Pride Parade and Festival; This Year's Parade and Festival Will Be Held On Saturday, Oct. 3
Photo of Ryan Cassata courtesy of eevees-photos
ANNAPOLIS, MD -- Accomplished singer-songwriter and award-winning LGBTQ activist Ryan Cassata (he/him) will serve as Grand Marshal and lead entertainer for the sixth annual Annapolis Pride Parade and Festival, Board Chair Jake Trudeau announced today.
This popular celebration of the local LGBTQIA+ community will be held on Saturday, Oct. 3, with the parade starting at 11 a.m. and the festival following at noon.
"We are beyond thrilled that Ryan Cassata will not only serve as our Parade Grand Marshal but will also be the headliner during the festival," Trudeau said. "Not only is Ryan a brilliant singer-songwriter, he also has been at the forefront of the transgender liberation movement since his early teens, turning early hardship and severe middle school bullying into a nationwide platform for education and visibility.
“Since then,” Trudeau added, “Ryan has become an influential speaker at hundreds of schools and universities nationwide, brought his advocacy all the way to the White Housse, and earned U.S. Congressional recognition. His inspiring story is also one that I can personally relate to, and I can’t wait to hear him speak and perform on October 3rd.”
Reflecting on the significance of the Annapolis Pride event, Cassata emphasized the power of representation in this moment.
"We're living through a moment in history where the U.S. government and political forces are actively pushing trans people down and trying to erase us," Cassata said. "But trans people have always existed and we will always exist. I'm proud and excited to bring trans visibility, and specifically trans FTM (female-to male) representation, to the stage with my all-trans band, D.I.Y. Guy."
As an award-winning artist, published writer, and activist, Cassata broke ground for transgender visibility long before trans stories entered mainstream media, including a milestone appearance on The Larry King Live Show in 2009 as an openly trans teenager. A recipient of the prestigious Marcella Althaus-Reid Award for his work in queering theology and the inaugural recipient of the Harvey Milk Memorial Award from his and Milk's shared alma mater, Bay Shore High School, Cassata's work continues to be featured across premier platforms including CNN, GRAMMY.com, Rolling Stone, Billboard, The New York Times, Newsweek, and The NY Daily News.
Musically, Cassata has built a remarkable career, with more than 850 national and international performances, eight critically acclaimed albums of original music, and millions of streams. He made history as the first openly trans performer at the Vans Warped Tour and has graced renowned stages such as Jazz at Lincoln Center, Global Pride, and SXSW.
The route for this year’s Annapolis Pride Parade will once again begin at Calvert and Bladen Streets, go around Church Circle and up West Street to end at Amos Garrett Blvd. The Festival will take place at the Bates Athletic Complex.
The theme of this year’s Annapolis Pride Parade and Festival celebration is “United In Pride, Together We Thrive."
A specially designed logo for the 2026 Parade and Festival (see logo below) was designed by queer artist Oli Bennan (he/they) of @birds.and.gay.stuff.
Additional details about the 2026 Parade and Festival will be announced as they are finalized.
For more information and complete biographical details, visit ryan cassata.
