Former President Obama makes Martha’s Vineyard comeback

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

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 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.

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.



  1. Gosh, we wish the stability of the Obama leadership could make a comeback to our country. Instead, we have the saber rattling of two lunatics who have the potential to tragically destroy us all. Their aggressive bluster draws us closer to war, which would, of course, distract from the Russian mess Trump is in. Making idiotic and dangerour threats that have to do with “who’s gonna pay for the wall” or “fire and fury” are words from a conman lunatic, no different from what comes out of NK.

    “The danger which troubled my husband was that war might be started not so much by the big men as by the little ones. While big men know the needs for self-control and restraint, little men are sometimes moved more by fear and pride.”
    Excerpt from a letter by Jackie Kennedy to Khruschev after JFK’s assassination re: the Cuban missile crisis.

    If only an Obama-like calmness could make a comeback to our country. If only anyone but Trump were at the helm now, we’d all be safer.

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