From Grant to Obama, Presidents have been traveling to the region since the 1870s

When the President of the United States goes on vacation, it’s big news. This past summer President Barack Obama put Martha’s Vineyard in the national spotlight once again when he and his family arrived for their seventh summer getaway on the island. But Obama is hardly the first Oval Office holder to visit. As it turns out, the President has been traveling a well-trod path between Washington and the sandy shores of Cape Cod and the Islands.

The first sitting U.S. president to visit Cape Cod was Ulysses S. Grant, who occupied the White House from 1869 to 1877. Grant may also hold the distinction of having visited more sites on the Cape than any of his future counterparts. On August 27, 1874, Grant arrived on Martha’s Vineyard in late afternoon on the steamship River Queen and was taken with his party by horse-drawn carriage to the Methodist Campground at Oak Bluffs. “So great was the press, notwithstanding the five or six thousand who were congregated in and about the grandstand, that there was difficulty in extracting the party from the cars,” noted the next day’s Martha’s Vineyard Times.

The following day, the president, his wife, and several other dignitaries took the River Queen to Hyannis, stopping briefly in Nantucket. From Hyannis he embarked on a whirlwind train tour that included stops in Yarmouth, South Dennis, South Wellfleet, Harwich, Provincetown, Barnstable, and Sandwich. The President received an “Enthusiastic Reception Everywhere,” according to a headline in the Sept. 1, 1874, Barnstable Patriot. Despite the fact that it was nearly 9 p.m. by the time the presidential party reached Sandwich, “a vast assembly greeted the distinguished visitors,” the newspaper stated. “Bands were in attendance, bonfires were kindled, and quite a jollification was indulged in.” From Sandwich the train moved on to Woods Hole, where the president and his party boarded the River Queen to return to the Vineyard.

Lured by the promise of sea air and good fishing, Grover Cleveland, the only U.S. president to serve non-consecutive terms, bought a summer home in Bourne in 1890, which he named Gray Gables. The Cleveland family and friends received news of his renomination in June 1892 via a telegraph line installed in the home, according to the Bourne Historical Society. Shortly after, the Old Colony Railroad erected a train depot at the site. Two of the five Cleveland children were born at Gray Gables.

“Mr. Cleveland was . . . seemingly more interested in his growing family and his fishing than in warring politicians,” wrote M.E. Hennessy in the October 23, 1933, Boston Daily Globe, recalling the conversations the ex-president had with a small group of reporters on the veranda of Gray Gables in 1892. “He lived the simple life, lounged about in old clothes, and appeared delighted that he had found a spot where he could get complete rest and recreation, without much publicity, and where he could restrict his callers to those whom he liked.”

The Kennedys enjoy family time on the Cape. Photo courtesy of the John F. Kennedy Hyannis Museum.

Gray Gables became an inn, but was destroyed by fire in 1975. The train depot was moved to the Aptucxet Trading Post grounds the following year. In 2006, Francis W. Madigan Jr. built a house on the Gray Gables site. While zoning regulations precluded his building an exact replica, the home was designed and constructed to resemble Cleveland’s “summer White House.”

The Pilgrim Monument drew two sitting presidents to Provincetown—Theodore Roosevelt to lay the cornerstone on August 20, 1907, and William Howard Taft three years later to celebrate the monument’s completion.

President Roosevelt sailed into Provincetown Harbor on the morning of the ceremony from his home in Oyster Bay, Long Island, on the presidential yacht, coincidentally named the Mayflower, according to The Pilgrims and Their Monument by Edmund J. Carpenter (D. Appleton & Co. Publishers, 1911). The president rode in a carriage through town accompanied by Massachusetts Governor Curtis Guild and J. Henry Sears, president of the Cape Cod Pilgrim Memorial Association. Mrs. Roosevelt and the President’s son, Quentin, and daughter, Ethel, followed in another carriage.

In his speech, Roosevelt praised the Puritans for their “iron sense of duty” and “will to do the right.” He urged the Puritans’ descendants to shape modern industrial civilization with the same “justice and fair dealing,” noting that different conditions call for different laws and government methods, including greater control over businesses and corporations. Recalling the speech three years later, the Sandwich Observer noted that Roosevelt spoke “before a large assembly across whose heads and the sand dunes of the Cape he shouted a memorable defiance to certain corporate interests.”

Preparing for the arrival of President Taft to dedicate the monument on August 5, 1910, downtown Provincetown had “the appearance of Mardi Gras time,” according to the Sandwich Observer (August 9, 1910). Warships and small boats filled the harbor, crowds filled the streets, buildings were covered with bunting and flags, and peanut and souvenir vendors did a brisk business, the newspaper wrote. The President arrived, like Roosevelt, in a yacht named the Mayflower.

In his address, Taft called the early Pilgrims “humble men whose faith was extreme in its simplicity and stern. The spirit which prompted them to brave the seas to land on this forbidden coast in winter, and to live here, has made the history of this country what it is.” Following the ceremony, the President and some 400 guests enjoyed lunch at the “handsomely decorated” town hall.

President Barack Obama, his wife, Michelle, and daughters Malia and Sasha greet top brass during a recent landing at Joint Base Cape Cod. The first family spends time on Martha’s Vineyard every summer, flying to the Cape aboard Air Force One, and then to the Vineyard aboard the helicopter, Marine One. Courtesy of Otis Air National Guard Base

Like Cleveland, John F. Kennedy, who occupied the White House from 1961 until his assassination in 1963, had a summer home on Cape Cod. And he left a very special legacy in the form of the Cape Cod National Seashore.

JFK’s father, Joseph P. Kennedy, and his wife Rose, purchased a home on the water in Hyannis Port in the 1920s, according to the John F. Kennedy Hyannis Museum’s website. That home, with two nearby homes purchased by their sons John F. and Robert Kennedy, became the Kennedy Compound and the center of the political universe in the early 1960s.

James Dow of Centerville recalls waiting outside St. Francis Xavier Church on South Street in Hyannis in 1961 and ‘62 after he finished his Sunday morning paper route for a glimpse of the President and First Lady. He’d set his bike against a streetlight and stand by the back entrance “just to get a look at the President of the United States.” It was remarkable how little security there was, Dow recalls. “He walked out of church and right past me. … I had no trouble getting a great look.”

On August 7, 1961, seven months after moving into the White House, President Kennedy signed the bill authorizing the Cape Cod National Seashore, thereby protecting some 40 miles of Atlantic coastline on the Outer Cape. In his remarks, Kennedy told the assembled dignitaries, “From personal knowledge I realize very well how useful this is going to be for the people of the Cape and Massachusetts and New England and the entire United States.”

Nearly 30 years later, President George H. W. Bush made a brief stop in Mashpee on Nov. 1, 1990, to stump for Republican office seekers, including William Weld, who was elected governor of Massachusetts five days later. In remarks delivered at Mashpee Middle School, the President said, “Let me say how great it is to be back on the Cape, to breathe the deep magic of this place. … Way back in 1943, in the fall, just about this time in 1943, I spent some time at the Cape, stationed at the naval air station, then at Hyannis. I’ve never forgotten the joy and the wonder of the Cape.”

Throughout the 1990s, Bill Clinton, who served as president from 1993 to 2001, made several visits to Martha’s Vineyard with his family, beginning in the first summer of his presidency. The Clintons reportedly enjoyed golf, bike rides, and shopping in local bookstores. Recalling those visits in a 2008 article in the Vineyard Gazette, Jim Hickey wrote, “President Clinton’s gregarious nature was well known around the Island, and there are many tales of routine shopping excursions or downtown strolls that turned into massive traffic jams as the Clintons stopped to talk with seemingly every Islander or vacationer within hailing distance.”

Also known for his friendships with Hollywood celebrities, Clinton celebrated his 51st birthday on the island in 1997 with a clambake at the Vineyard home of actors Ted Danson and Mary Steenburgen, according to Reuters. Guests included singer Carly Simon, television talk show veteran Merv Griffin, author William Styron, Washington power broker Vernon Jordan, and musician Jimmy Buffett, who sang his signature song “Margaritaville,” the news agency reported.

President Barack Obama has also made Martha’s Vineyard his family’s number one summer vacation destination, visiting the island every summer but one of his eight-year tenure in the White House. This summer’s vacation followed the pattern of previous years, according to reports in the Vineyard Gazette. “The 15-day vacation was quiet and low-key,” Sara Brown wrote in the Gazette. “The President played 10 rounds of golf. … The First Family spent four afternoons at a private beach in Edgartown, and per tradition, watched the Oak Bluffs fireworks show Friday from Ms. [Valerie] Jarrett’s Oak Bluffs home.” The Obamas also visited a range of restaurants across the island.

Lory Reilly, manager of the Nashua House Hotel in Oak Bluffs, says she had her first presidential sighting this summer, when President and Mrs. Obama had dinner at a local restaurant. “I saw his head go by when he was passing the hotel,” Reilly reports. She added that the security requirements were very thorough during the visit.

While she would have liked to get a closer look at the President (and maybe have him sign a denim jacket she decorated with his image when he was running for his first term), Reilly says she has no complaints about the security precautions. In the current climate, she says, “I think it’s very wise.”

Ellen Albanese is a freelance writer and editor who lives in Waquoit.