Jessye Desliva in Concert
at the Gloucester Meetinghouse, June 14 2026
Jessye DeSilva infuses hope into songs about religious alienation, mental health struggles, and societal injustice to create a uniquely queer and unholy ruckus. Jessye’s newest album Glitter Up the Dark, produced by Aaron Lee Tasjan, is getting rave reviews.
For more info on the artist, visit https://www.jessyedmusic.com/
3:30 PM - 5:30 PM
Gloucester Meeting House Foundation
10 Church Street
Gloucester, MA, 01930
More Info & Tickets Here
“QUEER Karaoke”
at Harbor9 Golf Sports Bar Saturday June 20th
For all LGBTQIA+ folks and friends, 18+ (IDs will be checked). NO COVER! Queer Karaoke begins at 9:00pm.
Join your hostess Dr. Viola Voila for the 2nd Annual night of queer karaoke joy and community at Harbor9--if you missed this last year, you probably heard how great it was, so get it on your calendar now!
Harbor9 Golf Sports Bar
355 Gloucester Crossing Rd.
Gloucester, MA, 01930
Teen Sail on the Schooner Adventure
Thursday June 25th FREE!
FREE private sail for teens ages 13-18, featuring the acoustic duo from Kicked Off the Bus Band and food by The Common Crow Natural Market, with trained adult chaperones from Younity and Schooner Adventure staff and crew.
5:15-8PM
Important!! You must pre-register HERE.
Cape Ann Pride is a grassroots coalition of LGBTQIA+ people of all kinds, and our Allies, who live and/or work in Greater Cape Ann, MA.
Our mission is to advocate for, bring together, celebrate, educate about, and support LGBTQIA+ people through a wide range of events and programs.
CALENDAR OF EVENTS FOR CAPE ANN PRIDE 2026