This weekend was one of fine dining, high fashion and philanthropy in Edgartown. The Taste of the Vineyard, an event many say marks the beginning of the social season on the Vineyard, celebrated its 29th successful year.

By long tradition, the Taste consisted of two separate events — a gourmet food stroll, which took place on Thursday, and a Patrons Party and Gala Auction, which took place on Saturday.

All told, the events raised more than $400,000 for the Martha’s Vineyard Preservation Trust, a nonprofit organization that is the steward of 20 historic Island landmarks. Among the properties the Trust preserves and protects are the Old Whaling Church, the Flying Horses Carousel and Alley’s General Store.

On Saturday night, the grounds of the Dr. Daniel Fisher House, also a Trust property, buzzed with chatter as patrons mingled at a cocktail hour and perused items in a silent auction. Among the items available for purchase were paintings by Island residents Christopher Crofton-Atkins and Margot Datz, and photographs by Edgartown resident Bob Avakian. Ms. Datz is the artist who repainted the mural in the Old Whaling Church.

After enjoying cocktails and hors d’oeuvres, the 250 guests gathered beneath a festively decorated tent for dinner and a live auction.

More than 1,000 people came to Taste of the Vineyard stroll Thursday night. — Ivy Ashe

Trust president Sally Rorer thanked those whose hard work and dedication made the Taste possible. She also took time to reflect on four individuals who have died in the past year and who made significant impacts on the Trust: Walter Eberstadt, Ray Ellis, Paul MacCowatt and Susie Whittemore.

“I’m confident their souls are with us tonight,” she told the crowd.

Mrs. Rorer also recounted restoration projects the Trust has accomplished in the past year, including repairing the 1876 mechanism that supports the Flying Horses carousel platform and fully restoring the Fisher House.

Amid the good spirits and cheer was the noticeable absence of a longtime benefactor, Ray Ellis. Mr. Ellis was a renowned painter who died in October at the age of 92. For 25 years, he had donated one of his paintings or a chance to hang out with him as the big-ticket item for the live auction. Altogether, his donations raised over $ 1 million for the Trust.

And even without him, this year was no exception to his tradition of giving. On Saturday, the Trust auctioned the last Ray Ellis painting they will ever auction, a piece called A Chilmark Pond. The painting sold — with a standing ovation — for $185,000 to Wendy Reily, one of the founders of the Taste of the Vineyard.

The painting, which depicts a peaceful scene of a sloping pasture near the water, once hung over Mr. Ellis’ own mantel. Mr. Ellis’s wife Teddie donated it to the Trust from her personal collection this year.

Sultans of Swing at Best of Vineyard stroll. — Ivy Ashe

In his 1995 book Martha’s Vineyard: An Affectionate Memoir, Mr. Ellis described his love for this particular painting: “Shortly before Beetlebung Corner, there is a farm on Middle Road that I have always loved. You can see the ocean just over the stand of trees, behind the pond. This tranquil, pastoral scene hangs over our mantle and gives us quiet joy daily.”

Trust executive director Chris Scott spoke fondly of Mr. Ellis’s legacy.

“It’s rare in your life that you meet someone like Ray Ellis,” he said. “He was extraordinarily generous, very committed to what we do. He was unique, truly unique, and will be missed by all who knew him. He was not just a talented artist, but an absolutely wonderful person, very entertaining guy, and a really dear friend. The amount of life and history he saw was phenomenal. He captured the spirit of Martha’s Vineyard like no one else has.”

Overall, the Saturday event raised $306,000 — $275,000 from the live auction and $31,000 from the silent auction.

Thursday’s stroll raised $133,000 in ticket sales before expenses.

On Thursday evening, more than 1,000 people packed into tents pitched on the lawn of the Dr. Daniel Fisher House for the stroll. Eighty-five different food and drink vendors set up stations where guests could stop by and fill their dinner plates with samples.

Food ranged from simple classics like lobster from Bill Smith’s Martha’s Vineyard Clambake Company and pulled pork from Smoke’n Bones to more refined dishes. Herring Run Kitchens and Provisions served Indian pakoras, a type of vegetarian fritter. Beetlebung Farm prepared slices of sweet pea olive oil cake and mint custard finished with mint leaves, mint syrup, and pea tendrils.

Nick Catt, co-owner and partner of Porto Pizza, said his favorite part was “when everyone first comes through the door like a stampede and the place fills up.”

Leading up to the event, the line of guests waiting to be admitted spanned nearly two blocks.

Beautiful dresses and well-coordinated outfits are a highlight of the event. Clothing ranged in color from summery pastels to more bold selections, like one man’s American flag-patterned suit.

“It’s amazing. I think it’s the best event I’ve been to in a long time,” said Edgartown resident Steve Carr. “It’s fantastic. It’s amazing. A great party, a great showing, great people, Everybody’s happy. It’s a great way to start the summer.”

Photo gallery: Strolling the Taste of the Vineyard.