This weekend, Islanders flocked to the Vineyard drive-in for the 20th annual Martha’s Vineyard Film Festival, a milestone celebration rescheduled from the spring.

Building off the summer’s successful drive-in movie series, coordinators brought the annual festival back to life with a weekend worth of screenings and live music.

“It’s completely different than we originally envisioned, but that’s part of the beauty of it,” said festival programming director Brian Ditchfield.

The festival began on Thursday and was supposed to conclude on Monday. But the final leg of the festival on Sunday and Monday evening was rescheduled for next weekend, due to emergency cleaning measures at the ice arena and poor weather conditions, according to Mr. Ditchfield. The Boy From Medellin will play at 7 p.m. on Friday, Oct. 16 and I Am Greta will play at 7 p.m. on Saturday, Oct. 17 following a short film produced by the film festival production team about climate change on the Vineyard.

All weekend long rows of cars settled into the ice arena parking lot, some people huddled in the trunks of their cars and others bundled in sweaters and blankets in the beds of pick-up trucks.

The DeWitt family, who attended screenings with their dog Butler on Thursday and Saturday, said the drive-in has been a highlight this summer.

“This is probably our fifth movie,” said Ann DeWitt on Saturday. “It’s just been the greatest experience.”

“It’s kind of like getting back to the olden days...It’s a different experience,” said Saturday movie-goer, Althea Freeman-Miller.

The festival opened on Thursday evening with The Way I See It, a documentary by Island resident Dawn Porter about Pete Souza, the chief White House photographer in the Obama administration. The screening was introduced by Ms. Porter over Zoom.

On Friday, the festival played the Dark Divide about a camper on a search for a new butterfly species, with a live musical performance by Johnny Hoy and the Bluefish.

On Saturday night the festival screened its first double-feature, playing two films originally slated for the March event. The first film, the Zeno Mountain Farm’s musical Best Summer Ever, was introduced by director Mike Randa with appearances from writers, producers and lead actor Shannon DeVido.

Mr. Ditchfield said the movie was a highlight of the weekend, with audience members cheering throughout the film.

“I have been looking forward to screening Best Summer Ever since we scheduled the film back in March,” said Mr. Ditchfield. “It was everything that it was built to be, every number everybody was jumping up. It really had such wonderful spirit and energy.”

Saturday’s second film, a documentary homage to the former Oak Bluffs shellfish constable Richie Madeiras, called Somewhere with No Bridges, drew similar crowds, many of whom knew Mr. Madeiras personally. Between films, musician Mike Benjamin strummed a set of acoustic songs for the audience.

In conjunction with Indigenous People’s Day weekend, the festival also hosted live performances from Wampanoag musicians like the Black Brook Singers and flautist Carol Vandal.

“It’s a special honor to have them with us over indigenous peoples weekend,” said Mr. Ditchfield.

The drive-in will continue through Halloween, with a selection of new films already lined up, including the not-yet released Borat sequel and the new documentary about Justice Ruth Bader Ginsburg called Ruth.

“I think part of what makes it amazing is the resiliency of the organization and the resiliency of the community and that we still find ways to gather and share stories,” said Mr. Ditchfield, reflecting on the success of the festival. “At the core of what we do is more than movies and it’s been so amazing for us that people continue to come out.”