This year’s annual pride parade in Oak Bluffs modeled exactly what the event stands for—inclusivity. The parade included everything from miniature horses wearing colorful sneakers to a drag queen lip syncing on the back of a Rolls Royce convertible.

On Saturday afternoon, Islanders of all ages gathered to celebrate the Martha’s Vineyard’s fifth annual pride parade, hosted by the Oak Bluffs Association. Vehicles covered in pride flags and festively dressed marchers all traveled up Circuit avenue before gathering at Ocean Park, where live music by The Femmes, a photo booth and a resource tent with local organizations awaited them.

Wearing a rainbow American flag top hat, Dan Waters stood at the edge of the park trying to capture the perfect shot with his film camera.

Drag Queen Lexacon rides in style. — Jeanna Shepard

“I spend the entire time trying to find the one shot that tells the story and there isn’t a single shot,” he said. “It’s all in every individual face, every individual sign....”

Mr. Waters said his first pride celebration was the 1987 Boston pride parade, long before the Vineyard parade started.

“At that time, the Island was just getting this gay community together, it was a scary thing,” he said. “And by ‘89 we got a bunch of us from the Island to march in Boston for the first time.”

The Island group held a handmade banner that said “Martha’s Vineyard,” the V a pink triangle to represent LGBTQ+ pride.

Suzan Bellincampi shows her spirit. — Jeanna Shepard

Over the last few years, he’s witnessed the pride celebration evolve on the Vineyard.

“It’s really the younger generation that has taken this over,” Mr. Waters said. “And they’ve done a fantastic job.”

The youthful spirit he described was especially visible in the young children chasing each other through the park, pride flag stickers stuck to their faces. The parade was a kaleidoscope of costumes, colors and music.

When the celebration moved to Ocean Park, spectators cheered and waved mini pride flags from the sidewalk as cars and people passed by.

Rebecca Gilbert and Dan Waters. — Jeanna Shepard

Drag Queen Lexacon was met with particularly loud cheers when she rolled through the parade on the back of a Rolls Royce convertible, her blue sequin dress catching the sunlight as she lip-synced Breaking Free by Ariana Grande.

This was Lexacon’s fourth time attending the parade in Oak Bluffs, but it was her first Vineyard Pride in full drag.

“I’ve done a lot of pride parades in drag but this is my favorite type of pride because it’s a small town, and it’s just so much more community,” she said. “I feel the love a lot closer—it’s great.”

Over the last four years, Lexacon has seen the parade expand to include more people.

This sign says it all. — Jeanna Shepard

“It reminded me that there is queer community on this Island that doesn’t always get enough attention,” she said.

Alexandra Pratt, director of the West Tisbury Public Library, emphasized a similar sentiment about the importance of support from the Island community. The Vineyard Library Association has participated in Vineyard Pride since the first year, she said.

“Especially for the libraries, we are for everyone, that’s our purpose, to be a community resource for everyone,” Ms. Pratt said. “LGBT books save lives, it’s a true statement. It’s important that everyone sees representation and diversity in books.”

Ben Hughes, who participated in the parade with the Upis Land brass band, mentioned how important it is to celebrate everyone for who they are, now more than ever.

“I think it’s really important in this climate to just be kind, have fun and let people be whoever they want to be,” he said.