When comedian Seth Meyers returns to lead the 45th annual Possible Dreams fundraiser Sunday, he welcomes the opportunity to get back to work. After all, his show has been on hold since the Writers Guild of America went on strike in May.

“The most depressing thing is how excited I am to step in front of people again,” Mr. Meyers said. “My endless search to make strangers laugh at me continues.” 

Possible Dreams is the largest annual fundraiser for Martha’s Vineyard Community Service. Though tickets to the event are sold out, an online auction featuring 30 items is already underway and will continue until the end of Sunday’s event.

Eight additional experiences are auctioned off live during the fundraiser, including a day on the set of hit television show Yellowstone and the fundraiser’s highest-raising auction item during the last few years: tickets to Late Night with Seth Meyers.

It was during the pandemic that Mr. Meyers first hosted Possible Dreams over Zoom. He said that during Covid, he became aware of the breadth of the organization’s work. 

“I was so impressed with the speed with which they serve the people who live here,” he said. “It made a lot of sense for me to help in any way I could, and it’s been massively different from year to year, based on location and weather.” 

Last year, Mr. Meyers said, the oppressive heat under the tent on Winnetu’s lawn led to a mid-auction costume change. Mr. Meyers switched from his sport coat to an oversized golf polo from the resort. Despite the hiccup, he said he met his annual goal of raising more money than the previous year.

“That wasn’t the best outcome for me on a fashion level,” he said. “But we did raise a lot of money, so I would just challenge the weather gods to hit us with their best because we’re going to raise the money.”

Mr. Meyers began visiting the Island with his wife, Alexi Ashe, who grew up making the journey from her home in New Mexico. Now, as seasonal residents, the couple visit every summer with their three children. Mr. Meyers said that contributing to this event is a way he can give back to the year-round community. 

“You come here for three months and you have a very different sense of what this community’s about — what this Island is,” he said. “It’s very helpful to see the scope and scale of what it is year-round and what the difficulties that certain people who live here face. For those of us who benefit from how special this is, it’s nice for us to have a place to give back.”

Beth Folcarelli, CEO of Community Services, said that the celebrity presence at the event contributes to the fundraiser’s success.

“We’re so humbled by Seth’s generosity and so many others who step forward at Possible Dreams and at other times when needed for the organization,” Ms. Folcarelli said. “The star power matters because it adds to the fun. It draws attention to the needs of the Island and it really demonstrates how caring some of those who are very fortunate on the Island are about Martha’s Vineyard, about the organization and about people who live and work here year-round.”

Many auction items are donated by some of the Island’s biggest names. Among them are pizza and a movie with actor Jake Gyllenhaal, attending a taping of Finding Your Roots with Henry Louis (Skip) Gates Jr., and a private dinner for two with Seth and Alexi Meyers, Tony Shalhoub and Brooke Adams, Ariel Ashe and Zachary Heinzerling, and Tom and Joanne Ashe, for a meal prepared by James Beard Award-winning chef Chris Fischer. 

Additional donations from local businesses make up the rest of the auction items, including four rounds of golf across courses on the Vineyard and Nantucket, works by local artists and Ms. Folcarelli’s personal favorite, A Dream Fit for a Foodie, which includes cooking lessons from several local restaurants.

An old hand at hosting the auction, Mr. Meyers has one tip for bidders. 

“If you know you’re going to bid, just start bidding early,” he said. “No one likes that over-dramatic person who waits until the last minute and then jumps in, because auctions can drag on. So just pick your number, get it out there early and let’s keep things moving.”