The Possible Dreams auction and fundraiser raised more than $570,000 on Saturday for Martha’s Vineyard Community Services (MVCS).

The annual event, hosted at Allen Farm in Chilmark, is the organization’s biggest fundraiser of the year, and for the seventh year in a row was emceed by Seth Meyers. 

Wiet Bacheller and Larkin Stallings flank Art Buchwald Award winner Nevin Sayre. — Jeanna Shepard

“We don’t have to hear much about our Community Services to realize how important it is on this Island,” Mr. Meyers told the Gazette. “And again, you want everybody who spends time on this Island to enjoy it as much as you do.” 

Community Services is a sprawling social services nonprofit that provides an array of programming to support Islanders experiencing domestic violence, navigating mental health challenges or recovering from substance use disorder. The organization also supports seniors, veterans, people with disabilities and children and families. 

“Possible Dreams isn’t simply an auction,…it’s a celebration of community,” said Dr. Nancy Monestime-Williams, member of the MVCS board of directors and the chair of Possible Dreams. “It’s neighbors helping neighbors. It’s people coming together to ensure that MVCS can continue providing vital programs and compassionate care to individuals and families across our Island.” 

This fall, Community Services expects to open its new campus in Oak Bluffs, a $17 million project that will consolidate services in a single building center. 

Before the auction, Mr. Meyers joked with the audience about how the Island is trying to kill him, between the ticks and flying Cape Air, he said. But it doesn’t stop him from participating in many Island events — Mr. Meyers attempted a mile swim during Swim Across America, and crushed his two sons in the Chilmark Road Race this weekend. 

“Not even a little bit close,” he said. “One day you’ll be older and you’re gonna run circles around me — not today, boy. Not today.” 

Among the items auctioned off at the fundraiser was a day of paddleboarding with Nevin and Stina Sayre. Mr. Sayre, a Vineyard Haven resident and professional windsurfing champion, was honored at the event for his annual “Round the Vineyard Challenge” fundraiser for Community Services.

Get your paddle up. — Jeanna Shepard

For the third year in a row, Mr. Sayre will sail 55 miles (70-90 miles with tacking and jibing) around the entire Island using a wing foil. In the past few years Mr. Sayre has raised more than $100,000 for Community Services, adding to his fundraiser efforts in the 1990s and 2000s that invited traditional windsurfers to race around the Island. 

For his efforts he received the Art Buchwald Award for outstanding community service. 

“It’s a lot of miles, but in this time of stormy seas for our country, we all have to put in the miles,” said Mr. Sayre in an emotional speech.

The organization also honored Jessica Garcia-Widra, who organizes a new mahjong fundraiser, called Tiles and Tea, in support of Community Services. 

Mahjong was a hot commodity during the auction, conducted by auctioneer Robbie Gordy. Audience members bid on a mahjong game with actress and comedian Kristen Wiig, who made a surprise appearance at the end of the event. 

“I’m a good time,” she said, sweetening the pot with the promise of snacks and a re-enactment of a scene from Dexter, a TV series about a serial killer. Two audience members won the prize for $16,000 each, raising a total afternoon-high of $32,000. 

Dexter was also an official item up for auction — or at least the chance to be a featured extra in the show. Dexter actor Dominic Fumusa helped introduce the opportunity, and actor and Island resident Tony Shalhoub got in on the bidding. 

“Oh no, an out of work actor!” said Mr. Meyers. 

Surprise guest Kristen Wiig joins Seth Meyers on stage. — Jeanna Shepard

“You can’t let Monk be the guy who brings down Dexter,” said Mr. Gordy, encouraging more bidding before Mr. Shalhoub gave up. 

Mr. Meyers, a seasonal resident of Chilmark, is also performing at a fundraiser for the Chilmark Preschool, and in July hosted a bowling fundraiser for Harbor Homes of Martha’s Vineyard. 

“It’s so fun when people like Tony, and Kristen and Dominic are here,” he told the Gazette. “When they get on stage…you can just feel the community in the room, and everybody just kind of works together.” 

Other prizes included a walk in Central Park with Mr. Shalhoub, tea and book club with best-selling author and Vineyard Haven seasonal resident Belle Burden, tickets to Boston Red Sox and Washington Capitals games, and lunch with Larry David at the Chilmark General Store. 

“Larry wanted everybody to know that he’s not excited about it,” Mr. Meyers joked. “And that will make it all the more better.” 

“We don’t know if he’s even going to pay, to be honest with you,” Mr. Gordy added. 

“You will get to split up the bill with Larry David,” said Mr. Meyers during the bidding, to cheers from the audience. “He’s going to make so much fun of you for $8,000 to have lunch with him. That’s gonna be the best part.” 

The item went for $10,000. 

Attendees also had the opportunity to donate for a chance to win tickets to both Late Night with Seth Meyers and Meyers’ upcoming stand-up show with John Oliver.

“I push him [Oliver] around all the time, he often makes me meet people from weird places, so I’m happy to make him meet ones from my weird place,” Mr. Meyers told the Gazette. 

Fundraising will continue with an online silent auction, with bidding open until Aug. 12.