In 1983, the Ruth J. Bogan estate presented the Permanent Endowment for Martha’s Vineyard with a $60,000 gift to establish the Creative Living Award, given annually to one Island resident who embodies the fiercely creative, courageous and independent spirit of Ms. Bogan in her contributions to Island life. Over the past three decades, the award has gone to Island artists, musicians, craftsmen, doctors and naturalists.

In a rollicking, funny and poignant event at the Agricultural Hall on Monday night the award went to a truck driver. And truck seller. And the only man on Martha’s Vineyard who can move a grand piano to Grand Rapids, an ottoman to Ottawa and an 180,000-pound house two blocks up Main street in Vineyard Haven. And please don’t ask if he has a permit.

The man of course is Clarence A. (Trip) Barnes 3rd.

“Before we do anything, we have to correct something,” Mr. Barnes’s cousin Billy McCullough told a packed house at the West Tisbury Ag Hall.

“And what’s that?” said Emily Bramhall, executive director of the Permanent Endowment.

Mr. Barnes, flanked by his cousin Billy McCullough and Permanent Endowment executive director Emily Bramhall. “What happened to spirit?” he told the crowd. — Mark Alan Lovewell

“It shouldn’t be the Creative Living award,” Mr. McCullough said. “It should be the Wow, You’re Alive? award. Anybody who knows Trip wonders how the heck the guy is still alive.”

Mr. Barnes, whose business Barnes Moving and Storage is just as much of an Island institution as the 75-year-old himself, spurned his Park avenue, prep school childhood to make a life on the Vineyard. He worked as a milkman, became friends with the right people (and some of the wrong people), found money where there was none and started a business doing what he loved: moving as many hearts, minds, and occasionally, as much furniture as he could. He’s hosted auctions as unfiltered as the Camels he smoked and spent decades as the ire of lawmakers, bartenders, ferry workers, building inspectors and teetotalers.

Yet through the years, Mr. Barnes’s timeless red, green and yellow-painted 18-wheelers, styled more like they were meant to transport P.T. Barnum’s savannah predators than Allen Whiting’s artwork, became omnipresent Island totems of the equally colorful spirit and character of their driver.

On Monday night as the Permanent Endowment transformed the Ag Hall into Trip Barnes’s porch, equipped with rocking chairs and his plaster dummy, lifelong friends told stories about the lives Mr. Barnes had not only touched but often saved.

“We have Trip to thank for quietly taking care of so many Vineyarders who might have been down on their luck,” Ms. Bramhall said. “We have Trip to thank for the ice arena, for Vineyard House. Wherever you look, chances are very good that Trip has been behind the scenes getting the important work done.”

She was right. As the packed house listened to the evening’s hilarious porch stories, many couldn’t help but realize that Mr. Barnes was responsible for the barn they were sitting in too.

“There are a lot of things you used to be able to do that people say you aren’t supposed to do anymore, but I say why not,” Mr. Barnes said. “What happened to spirit?”

As a youngster in the 1970s, Mr. McCullough recalled he had the privilege of riding shotgun with Mr. Barnes while he completed the heretofore unprecedented New England grocery tour for Cronig’s Market.

“Everywhere he went, people embraced him, laughed with him,” Mr. McCullough said. “And my God, he knows how to have fun.”

Between stories of sinking ferries, saloon shootouts, forgotten permits and other yarns about all the fun Trip had in his life, everyone on stage agreed that Mr. Barnes was also one of the hardest workers they knew. His can-do ethic extended beyond his own ability to lift a refrigerator up a five-story Manhattan townhouse; he expected a similar devotion from his employees, many of whom were down-and-outers who came to Mr. Barnes as a last resort. Before he helped start the Island’s sober living facility, Vineyard House, Mr. Barnes unofficially provided a similar service in his upstairs loft.

“Over my office I’d always be drying a couple friends out,” Mr. Barnes said. “And I worked them to death, and I had a lot of luck with it. They’d work with me until they could go back to their regular lives, but moving furniture is a way of life, too.”

Allen Whiting, a former recipient of the Creative Living award, congratulated Mr. Barnes on his own sobriety.

West Tisbury painter Allen Whiting (left) called Mr. Barnes the Anthony Bourdain of the highway. Chris Scott (right), former executive director of the Preservation Trust, told tales from the days when Mr. Barnes was auctioneer at trust fundraisers. — Mark Alan Lovewell

“It’s why I’m here today,” Mr. Barnes said.

When neighbors of the proposed Vineyard House began to express fear about the project at selectmen’s meetings, Mr. Barnes came up with a foolproof way to quell their concerns.

“I found out who would complain,” Mr. Barnes said. “And I would go to their house, and knock on their door with a pie, and say, hi, I’m your new neighbor. We’re opening up a new sober house down the street and I think you may want to come spend a week there. And they all ran away.”

Mr. Whiting described “the Anthony Bourdain of the highway” as a natural fixer.

“The bigger the problem, the more Trip enjoyed fixing it,” Mr. Whiting said. “And the less he charged.”

When Mr. Barnes inherited a barn that was too small to store his hefty collection of wares, he decided to simply lift the thing higher.

“I told the policeman that I didn’t have a permit, because I couldn’t lie to him,” Mr. Barnes said, “and so I just hoped nothing would come of it. And nothing did. Who’s gone to jail for moving a house?”

Mr. Barnes raised money almost as well as he raised buildings. Chris Scott, former executive director of the Preservation Trust, said Trip had brought in more than $5 million auctioneering for the Trust alone, using phrases like “you’re my new best friend,” and “tie me to a tree and call me stupid,” to sell bird cages for $10,000, and Ray Ellis paintings for $250,000.

“When he sold that bird cage, I realized we had something,” Mr. Scott said. “People came for the show.”

Mr. Barnes would sell seats on a broken-down school bus for $1,000. He’d turn it into a tour bus, taking passengers to parts of the Island they’d never seen. One time he brought all 44 passengers into David McCullough’s house on Music street and started juggling the author’s two Pulitzer Prizes. Mr. Barnes called it the Magical Mystery Trip.

“I scared some people,” Mr. Barnes said. “But nobody said I’m never going on that bus again. They said when can I come back?”

Mr. Scott recalled the memorable night Mr. Barnes decided to sell Ray Ellis’s tie at the end of an auction.

“Ray would take his clothes off,” Mr. Scott said. “And the crowd would go nuts as Trip sold them. Trip had him down to his skivvies, all sweaty and naked, and the crowd was packing up, but then Trip said we should auction his tie. So he started the bidding at $25, and then $50, and then a guy in the back says, ‘I’ll give you 150. Thousand.’ So Trip says, ‘We’ve got $150,000 for the tie. Do I hear $160,000?’”

Trip sold the tie for $150,000 but the buyer gave it back to Ray Ellis. When Mr. Ellis died, his wife Teddy gave it to Mr. Scott. On Monday, with tears in his eyes, Mr. Scott presented the $150,000 tie to its original seller, Clarence Barnes 3rd.

Although Mr. Barnes has moved all over the country, he’s always been rooted himself on the Vineyard.

“I never wanted to live anywhere else,” he said. “I’ve been to every state in the Union except Hawaii probably five times and maybe more, and they’re all fun to visit, and I’ve even wanted to go back to one or two of them, but this is where I live and I love the people here and I love the Island.

“And what else is there? Things are changing, but it’s still inherently a fabulous place. And I just try to keep things the way they were. Sometimes I guess I’m a little loosey-goosey about the way I go about things, but it works. And if it works, don’t break it.”