UPCOMING EVENTS
Pride Services at local houses of Worship
St. John's Gloucester, Sunday 5/31, 10 am
48 Middle St, Gloucester, MA 01930
Essex Unitarian Universalist, Sunday 5/31, 10 am
59 Main St, Essex, MA 01929
West Gloucester Trinitarian, Sunday 6/7, 10 am
488 Essex Ave, Gloucester, MA 01930
Temple Ahavat Achim, Friday 6/12, 7 pm
86 Middle St, Gloucester, MA 01930
First Parish Church MBTS Pride Worship Service
Sunday, June 28th 10a-11a
10 Central St, Manchester-by-the-Sea, MA 01944
Join us as we celebrate the beautiful diversity of God’s good creation.
Jessye Desliva in Concert
Purchase concert tickets at the Gloucester Meeting House.
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/
Queer Karaoke at Harbor 9 Golf and Sports Bar
For all LGBTQIA+ folks and friends, 18+ (IDs will be checked). NO COVER!
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!
"Make Waves for Pride" dance/pool party at the Beauport Hotel in Gloucester.
Rescheduled! Join us for the return of the Birdseye Rooftop Sunset Sessions: Pride Edition, a fundraising dance/pool party at the Beauport Hotel in Gloucester. Purchase tickets at https://www.eventbrite.com/e/sunset-sessions-at-beauport-hotel-pride-edition-tickets-1987447802879?aff=oddtdtcreator
Manchester-by-the-Sea Progress Pride Flag Raising
Come out and show your support in Manchester!
Cape Ann Families Bowl with Pride (for FREE)
Cape Ann Pride has rented all of Cape Ann Lanes on Saturday May 30th from 12-2pm to provide a safe space for LGBTQ+ families. All LGBTQ+ and allies and their friends and neighbors are invited. This is a FREE event, but you must register. Register here: https://www.zeffy.com/en-US/ticketing/cape-ann-families-bowl-with-pride
The Illustrious Blacks/Dr. Viola Voilà/DJ Dance Party
Blast off into Pride month with the Illustrious Blacks, NYC's Afro-Electro-Disco-Space-Punks here to deliver you into intergalactic ecstasy! With special guest Dr. Viola Voilà and a set by DJ Salomon. Presented by Cape Ann Pride & Magma.
Saturday 5/30/26
Doors 7:00pm
Show 8:00pm
21+, Positive ID Required
Premium Seating with cocktail service: $39.50 + $6.95 service fee
Standard Seating with cocktail service: $34.50 + $6.95 serivce fee
GA Standing: $24.50 + $6.95 service fee
+ $5 Day of Show
Blast off into Pride month with the Illustrious Blacks, NYC's Afro-Electro-Disco-Space-Punks here to deliver you into intergalactic ecstasy! The duo the New York Times called "Bed-Stuy’s favorite creative couple” grace the clubs of Ibiza, Australia, New Zealand, Asia, Europe, UK, and Canada with their blend of DJing, performance art, and live music tracks .... and now they return after their jaw-dropping Gloucester debut last year for the Cape Ann Pride Weekend. Hostess extraordinaire Dr. Viola Voila will tantalize with her captivating performances and keep the party vibes flowing. DJ opener Salomon delivers deep, danceable tracks to get the party started.
Dr. Viola Voilà (she/her in drag) or Dr. Kasey Calebaugh (he/him out of drag) enjoys a wide range of musical endeavors as a violist, Suzuki music educator, and drag entertainer. They completed a Doctorate of Music Arts degree in Viola Performance from the Hartt School, graduating with the Regents’ Honor Award - the most prestigious award that the University of Hartford bestows on graduate students. They regularly film drag story hours and interview local residents at Ipswich Community Access Media, perform with the Cape Ann Symphony and Nonconformist Orchestra (the first and only transgender/non-binary, LGBTQ+ and minority inclusive professional orchestra), and serve on the Ipswich Cultural Council Board. As an active LGBTQ+ professional, they have been invited to speak at numerous high schools, perform for Hamilton-Wenham HRC Pride Picnic, World Pride DC 2025, & actively produce content with the Trustees.
Get Tickets at The CUT
Pride Kickoff at Drift
Head on down to Drift directly after the Pride Flag Raising at Gloucester City Hall (4PM) for the Pride Kickoff Party.
Pride Flag Raising at City Hall
Come out and show your support; join Gloucester City Officials for the official Pride Flag Raising.
Author Milo Todd visits
Friday May 8th 5:30PM: Free author talk on “transcestors” history by Milo Todd, author of the acclaimed historical novel The Lilac People at the Sawyer Free Library, signed paperback copies available for sale. Registration required at https://sawyerfreelibrary.assabetinteractive.com/calendar/hold-for-author-talk-milo/
Saturday May 9th 1-3PM: Writers’ workshop with Milo Todd at the Writers Center of Gloucester, Registration required at https://givebutter.com/writing-exercises-for-character-development-with-milo-todd-awgncb
