Hosted by comedian and late-night talk show host Seth Meyers, the Possible Dreams auction is the largest fundraiser of the year for Community Services, which offers childcare, mental health care and other services to the Island community.
The Possible Dreams auction and fundraiser raised more than $500,000 this weekend for Martha’s Vineyard Community Services.
The live auction was held on Sunday at the Allen Farm in Chilmark, a new venue for the event, and more proceeds from the event’s auction and other fundraisers were still coming in Monday.
Hosted by comedian and late-night talk show host Seth Meyers, the auction is the largest fundraiser of the year for Community Services, which offers childcare, mental health care, disability support services, aid to the recovery community and help for victims of sexual and domestic violence.
This was Mr. Meyers sixth year emceeing the event, and he auctioned off a cruise ship vacation, artwork and a private dinner at Dock Street Diner, to name a few dreams, with the help of longtime Community Services auctioneer Sherry Truhlar.
“Tonight is about what makes us all the same, and if you live on the Island, two things are true: One, you believe in the value of supporting an incredible organization like MVCS, and two, you live in constant fear that a tick bite will ruin your summer,” Mr. Meyers said, eliciting laughter from the audience.
Stepping onto the stage to introduce MVCS and to start off the event was Dr. Nancy Monestime-Williams, the chair of the Possible Dreams Committee and board member at MVCS.
“What is important about this is that it truly is the community supporting the community,” said Ms. Monestime-Williams. “We channel our energy to find ways to provide services to cover, to assist, and maintain the programs of MVCS. It’s incredibly important to me to be involved in anything that ties in the community and improves their well-being.”
Dean Teague, the CEO at MVCS, took on the lead role at the organization in March, and in only a few months it became clear how important Community Services is to the Island.
“People believe in their mission at MVCS,” he told the 200 people assembled Sunday. “They love what we do, and we have the opportunity to touch so many people’s lives. It’s genuinely humbling to witness the commitment during our work together every day.”
Community Services is in the middle of overhauling its Oak Bluffs campus and Mr. Teague said that the nonprofit has raised $13.5 million of its $17.5 million goal.
During Sunday’s ceremony, Community Services honored dedicated business owner, volunteer, and advocate Larkin Stallings with the Art Buchwald Award for outstanding community service. Mr. Stallings, the owner of the Ritz in Oak Bluffs, served on the MVCS board for nine years, ending in 2024
“Part of what’s so great for me with this is that it’s an opportunity to just give a little bit back,” said Mr. Stallings. “I feel so lucky and it’s so good to be surrounded by people that I care about, and I enjoy working with for so long and for an organization that means so much to my family and me.”
Community Services staff also took the chance Sunday to enlighten the audience about some of the work they do. Heather Quinn, the division director of the early childhood programs at MVCs, talked about her own experience in getting childcare for her son, and how these types of services keep the Vineyard running.
“I’ve heard Heather say this before when she started her work, if this program doesn’t work, the Island doesn’t work,” said Ms. Truhlar.
The live dreams auctioned off ranged from experiences such as a paid trip to Fenway Park, with behind-the-scenes tours and coveted tickets to the Red Sox that had a winning bid of $10,000, to a private fishing trip and shore lunch with Kenneth Cole and Johnny Graham, with a winning bid of $15,000.
“Seth and I are really here to cajole you,” Ms. Truhlar said amongst the laughter of the crowd. “We are not mean-spirited, we’re high-spirited.”
At one point, Mr. Meyers was joined on stage by actress and seasonal Chilmark resident Amy Schumer to help introduce one extremely popular dream. Possible Dreams auctioned off a family dinner for up to six guests with Seth Meyers and his family, along with Ms. Schumer, actor Tony Shalhoub, and actress Kristen Wiig.
The dinner will be prepared by Chef Ryan Scanlon, a Vineyard cook who was recently featured on Next Level Chef.
Joking with the audience, Ms. Schumer and Mr. Meyers made this item sound like a night to remember, while encouraging people to donate to MVCS.
“Things happen,” they said. “Marriages break up, and they get back together. We swing, we put our keys in a bowl, we get blackout drunk, it’s our personal favorite night of the year.”
“My husband will be there if you want to hear someone talk about how much the Island has changed,” Ms. Schumer added with a smile.
Their lively banter brought this item to be the highest winning bid of the night, totaling $40,000 for a seat at the Meyers family table.
Closing out the event, Mr. Teague re-entered the stage and told the audience how grateful he was for their donations to community services.
“I’ve never seen such generous people in my entire life,” he said. “So, thank you all so much.”

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An all island night
Max batzer AquinnahAn all island night
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