Martha’s Vineyard ready to welcome Obama family

Family can’t resist the Island, and is headed back to Chilmark for vacation.

In this file photo from 2015, President Barack Obama and First Lady Michelle Obama arrive on Martha's Vineyard by helicopter. — Michael Cummo

Updated Aug. 2, 4 pm

Former President Barack Obama and his family are coming back to Martha’s Vineyard and, specifically, Chilmark, to vacation.

“They’re coming in this weekend,” Ann Crook, general manager of the Martha’s Vineyard Airport, said. “I can’t get any more specific than that.”

Ms. Crook said it will be different from when the former First Family landed at Joint Base Cape Cod in Air Force One and then flew to the Island on Marine One.

“It’s a little more than your run-of-the-mill celebrity, but not much,” Ms. Crook said. A major difference from years past is the restrictions on airspace. Those will be nonexistent this time, she said.

There has been chatter about the former president’s family coming back to the Island for weeks, and it was more than speculation. Still, it’s been harder to confirm than in years past that President Obama, Michelle, Malia, and Sasha were coming back to the Vineyard, where they spent seven out of eight summer vacations while in the White House. The only year they missed was 2012, the year President Obama ran for re-election.

“It’s department policy not to comment on any guests,” Chilmark Police Chief Jonathan Klaren said when asked about the impending visit.

It went that way with pretty much everywhere we checked since the Island’s worst-kept secret started to trickle out.

On Tuesday afternoon, Massachusetts State Police spokesman David Procopio wrote in an email that troopers have been pulled in to help provide security for the vacation. “The Massachusetts State Police will be assisting the U.S. Secret Service with security operations for former President Obama and the former First Lady during their upcoming visit to Martha’s Vineyard,” he wrote. “Please note that we do not release specific details related to personnel numbers and tactics for security operations.”

The Secret Service would not confirm the former president’s vacation and, instead, referred questions to the Obama Foundation, which has not responded to a request for comment.

“As a matter of practice, the United States Secret Service does not provide information regarding the itineraries of our protectees,” special agent Joseph Casey wrote in an email.

An Island source has told The Times that rooms have been booked in Oak Bluffs for weeks for the president’s Secret Service contingent.

The Times even tried President Obama’s good friend, former Massachusetts Gov. Deval Patrick. A request for comment through Mr. Patrick’s current employer, Bain Capital, on whether Mr. Patrick would be coming to the Island for dinner with the Obamas was met with this response: “We totally appreciate your question but aren’t in a position to share Gov. Patrick’s travels,” a spokesman wrote.

A Farm Neck Golf Club employee, where the president has been known to enjoy a round or two or three, said he was not at liberty to discuss whether any tee times had been made for the lanky lefty.

In years past, former president Obama’s vacation getaway was this house at 72 Gosnold’s Way in Chilmark. — Photo by Nathaniel Horwitz

While the Obamas’ return to Chilmark is well known, the location of their rental house is surprisingly well kept. A Times reporter venturing down Gosnold’s Way toward the former first family’s digs at 72 Gosnold’s Way left with little information. After being told that seeking out the former first family is “not a good idea” by one man on the private road, she then encountered a group of women walking. “He’s not coming this year,” said a woman with twinkling eyes and a confident stature. A moment later, after being assured that the Obamas are indeed expected in the coming week, the woman faltered. “That was a lie,” she said sheepishly, “but I won’t say more.”

The Times received similar information from employees of the Captain Flanders House, a quaint inn located across the street from Prospect Hill Road, which eventually branches into Gosnold’s Way. “We can’t say anything. All we know is that he will be here this weekend,” said a young woman who declined to be identified.

Sources peg the arrival of the former president’s family at August 6 and the family’s departure at around August 27, which would coincide nicely with Malia’s move-in day at Harvard University on August 22, according to the Ivy League school’s website.

Islanders seem generally at ease with the return of the former first family. “If there’s going to be one president or political figure to muck up our Island, I’m glad it’s Obama,” Aquinnah resident Faith Smalley told the Times.

Bill Rossi, a Chilmark selectman and a broker with an office at Wallace and Co. Sotheby’s International Realty, said he is pleased to share the Vineyard with the former president and first family. “It’s an honor for presidents to visit our town, and especially so for the past eight years. Every time the Obamas visit, it’s wonderful.” he said. Shortly after, Mr. Rossi mentioned that one of Obama’s assistants, Katrina, would be arriving shortly to discuss logistics for the family’s arrival. When asked about the Obamas’ vacation plans, Katrina declined comment.

Jenna Petersiel, owner of the Chilmark Tavern, holds out hope that the Obamas will make their first trip to the Chilmark Tavern this summer. “It would be an honor to serve the Obama family. I hope they come in,” Ms. Petersiel said.

Kim Rome, Island resident and creator of the “The real revolution will be love” bumper stickers, fills many roles on the Vineyard. Her reaction to the return of the former first family was a bit more nuanced. “I’m happy to have him come, but this place is filled with so much frenetic energy at this time — it’s a particularly bad year for frenetic energy — I just wish he could come in October.”

Chilmark resident Gary Stuber was more concerned for the former president’s well-being. “I’m happy that Obama is coming. Maybe now that he is no longer in office, he can relax and enjoy less scrutiny. After all he has put up with, he should be able to do anything he wants.”

If this visit is at all like former visits, it will feature the former president playing golf, and then playing more golf, interspersed with bicycling outings with his family, dining at favorite Vineyard restaurants, including Nancy’s (where first daughter Sasha has worked in the past), the Sweet Life Cafe, and others.

For a sense of how previous vacations have gone, check out these Times stories here and here.

Editor’s note: Updated to include comments from Vineyard residents on the return of the former first family.



  1. Remember how the deplorables used to complain about the First Family’s security being too costly during the President’s visits? Now with Mar-a-LaGoAway, Trump Tower, and his NJ golf club and the one in Jupiter, Fl, isn’t the silence from the deplorables deafening? And how could we forget all the disparaging remarks about President Obama playing golf too often? Seems kinda quaint now. Oh, for the good old days. Enjoy your well-deserved vacation time, Obama family. We miss you like crazy.

    • Who is we? You assume everyone shares your opinions, they are your opinions alone as is your comment. You may say: “I miss you like crazy”. A large part of the political dysfunction in this country is that many people do not consider that perhaps not everyone thinks like they do.

      • old man– you deflect the point . maxz’s comment is not an opinion.
        trump promised he would not take vacations, play golf etc while relentlessly berating Obama for said things. He now plays golf every weekend at the expense of millions of tax payer dollars, is on a vacation, rules by executive order, which he called Obama “weak” for ,and has lied about just about everything he has ever done, said or thought. That’s not opinion– that’s fact.
        And as a certain old man who changes identity often here said, ” it doesn’t matter if a leak was illegal, as long as it was true” But that was when the leak was damaging to Hillary..

        • Deplorables don’t care. Vacationing while black is what they objected to. And governing while female is what they objected to when it came to the possibility of Hillary. Trump is now seen as the laziest president in our history because that has what he has proven himself to be, and the deplorables don’t object. The Obamas brought education, aptitude, class, dignity, intelligence, reasoning, stength, ethical conduct, etc. to the White House, and the deplorables don’t object that Trump has none of that. Trump brings nothing except chaos and embarrassment, and deplorables don’t object. They don’t know enough to be ashamed because their own racism and misogyny outweigh all reason and what is good for our country. A weak, lazy, incompetent white male is in the White House and that’s just fine and dandy with the unAmerican deplorables. And, the mofuzz and oldman posters can’t understand that the “we and them” world of divisiveness that Trump promotes, even when speaking to Boy Scouts, is why we miss the Obamas like crazy.

          • 63 million voted for Trump and he got 2600 counties versus 490 for Clinton. All of these people are deplorables? Is it possible that Clinton was not a strong candidate? She lost because she got 2 million votes fewer than Obama did in 2012. 40000 votes would have turned it in Wisconsin, Michigan and Pennsylvania. Facts are inconvenient things.

          • How many times did you say “they”? The whole “we and them” concept- did you read your own comment? Maybe hypocrisy is also a one way street?
            I also hope they have a wonderful vacation.

          • Andrew: It’s time for conservatives to get over the election. The fact remains that #45 lost the popular vote. Regardless, for whatever ill-conceived notions any conservative voted for a conman liar with no impulse control, yes, if you now still support this lunatic, without any reverence for the diplomacy and tact of the Obama administration, you are indeed a deplorable.

  2. We is plural look it up. That means more than one, a week after posting, where are the others who sign on with Max? Don’t assume everyone or in your case “we” agrees with you. Try engaging in conversation with other people. Just because you can post doesn’t mean you speak for anyone else but yourself, others may agree, you are the only one posting. Therefore use: “I” it will also help you get past the denial stage in your life.

  3. Maxz. Yes the electoral college doesn’t matter. You win a baseball game by hits not runs scored and a football game by yards passed rather than touchdowns. Candidates would campaign differently if the election was about popular vote. Hilary didn’t need the extra 2 million in California and could have spent more time in Michigan and Wisconsin. Even you are smart enough to understand that.

    • Andrew, you really need to let go of the election. It’s been over for a while, you know. Pay attention to the damage #45 is causing as POTUS and how every major campaign promise has failed. Your guy is a loose canon lunatic on the same level as that other small man in NK. He was pathetic as a reality tv showman but he’s worse as a know-nothing president. Surely even you can see he is not informed or capable of anything except his stupid and dangerous bluster.

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