In thinking about his role as host of the 44th annual Possible Dreams Auction on Sunday, July 24, seasonal resident and late-night talk show host Seth Meyers sees himself as more a sidekick to auctioneer Sherry Truhlar’s superhero.

“This sort of Robin to her Batman is a role I take very seriously,” Mr. Meyers said in a phone interview with the Gazette. “You can’t step on the Bat rope, you’ve got to make sure you leave room for the auctioneer to do their thing.”

The duo will take the stage at the Winnetu Oceanside Resort in Edgartown at 4 p.m. Sunday with the goal of raising $500,000 for Martha’s Vineyard Community Services. The nonprofit provides a long list of social services, from support for victims of domestic abuse to mental health counseling to helping people living with addiction, that make up a large chunk of the Island’s social safety net.

Community Services relies on Possible Dreams, its biggest fundraiser, to make sure it has enough money to provide those resources, Community Services executive director Beth Folcarelli told the Gazette. The bulk of the money raised Sunday will go toward funding the Island Counseling Center and the Early Childhood Center.

“Those two cornerstone programs operate at sizeable deficits, so the money from Possible Dreams helps

to keep those two in particular operational,” Ms. Folcarelli said.

In addition to helping to keep the lights on, the auction is a way for the organization to spread its mission, Ms. Folcarelli said.

“Having a chance to be able to share with the community what we’re doing as an organization and the needs of Islanders is a huge part of this event,” Ms. Folcarelli said.

And its mission is an essential one made all-the-more important because of the pandemic, Mr. Meyers said.

Seth Meyers returns as host this year. — Ray Ewing

“The more time you spend on the Vineyard…you have a huge appreciation for the people who make it work year-round,” Mr. Meyers said. “And especially through the pandemic year, you just understood how invaluable they were to the community.”

The event is sold out — 200 people have bought tickets — and will be livestreamed. This will be Mr. Meyers’s third year as host, meaning he has watched the event crawl from fully online to partially in-person to mostly in-person, he said.

“Probably 20 years from now we’ll be doing it at Madison Square Garden,” Mr. Meyers said jokingly, referring to the evolution of the event.

This year there are 48 different dreams to bid on. Online bidding opened on Tuesday for 39 of the dreams, to include a cheese tasting at Grey Barn, a basket of Vineyard-related books from Bunch of Grapes and five passes to cut the line at Back Door Donuts.

“I know there’s a lot of great auction items this year because my mother-in-law was one of the people in charge of them and she won’t stop chewing my ear off about it,” Mr. Meyers said.

New dreams this year include a six-night stay at the Four Seasons in Vail, Colo., dinner with Mr. Meyers and fellow seasonal resident Amy Schumer and tickets to see Carly Simon get inducted into the Rock & Roll Hall of Fame. Avoiding repetition is the challenge to putting on the same event year after year, Ms. Folcarelli said, so she hopes the new dreams will help keep things fresh.

“After 44 years it gets tired and you really have to reinvent it and keep it dynamic and energizing for people,” Ms. Folcarelli said.

While Mr. Meyers will spend the event convincing people to open up their wallets, he said he feels particularly motivated to do so for the dream of which he is a part. A bidding war would go a long way for his self-esteem.

“They can expect during the auction just a real desperation from me and a real neediness to get that number up,” Mr. Meyers said. “It will have a great deal to do with my own sense of self, so do please bid on it.”

Turning serious, Mr. Meyers said he is happy to host the event because it is a way to show appreciation for a place that means a lot to him and his family.

“I found my way there through my wife’s family and now I’m really lucky to have kids who are spending a great chunk of their year on the Vineyard,” Mr. Meyers said. “It’s a place that’s near and dear to my heart and any little piece you can give back is the least you can do.”

While the live event is sold out, public participation in the silent auction remains open to the public online. To participate in the online auction, visit

For more information about Community Services, visit