Last summer, The Ritz Cafe hosted a one-night event to celebrate Pride Month that proved a hit with the Island community. The event was so popular that Larkin Stallings, the owner of the Ritz and president of the Oak Bluffs Business Association, immediately began planning a larger celebration for 2022.

“[The party last summer] turned out explosively big, it blew up into a really cool kind of thing,” Mr. Stallings said, earlier this week. “As a result, when I became president of the OBA, along with [vice-president] Sofie Green, we began talking about other events the OBA could be a part of and the obvious one was Pride. We came up with the idea for a weekend-long celebration. Next year we’re hoping to make it Island-wide.”

The festivities commence at 8 p.m. on Friday with a kick off party hosted by the Ritz, featuring live music by Adam Natusch and a set by DJ Scott Helms. A Cape Cod native, Mr. Helms has worked for the Hull Pride organization since 2013, while spinning discs on and off since the 1990s.

The weekend’s main event takes place at 3 p.m. on Saturday, with the Pride Parade marching from the Island Queen dock to Ocean Park. Following the parade, there will be a celebration and dance party, with the jazz/hip-hop band Funktapuss performing at the gazebo.

Other highlights around the Island include a Drag Queen Storytime at 10:30 a.m. on Saturday at the West Tisbury Library, where drag queen Missy Steak will read children’s books that celebrate diversity and different identities.

On Sunday Missy Steak heads to Oak Bluffs to host a drag brunch from 11 a.m. to 2 p.m. at Oyster Bar 02557 alongside drag queens Misery, Toast and Larissa Montes. The event is sold out but walk-ins may be accomodated.

The weekend wraps up on Sunday night with an after party at the Ritz. The theme of the event is 2Boys! 2Queens! and will include performances by Missy Steak and Toast, as well as a set by DJ AP beginning at 6 p.m.