After a 15-minute drive, headed to dinner at a restaurant with the first lady, Obama finally passed two women on the side of the road who stopped to wave and smile.
Despite a few rainy days that kept him off the golf course, Obama and his family are enjoying something they rarely get the rest of the year – a quiet community where nobody much cares where they go.
On this 96-square-mile island off the coast of Cape Cod, it's no big deal for a president to spend some down time. Chief executives since Ulysses S. Grant have made the trek for the fresh ocean air and wide open wetlands and woods.
This weekend, Democratic presidential candidate
The Secret Service long ago figured out how to secure the traveling
President Clinton loved the pastoral views, long Atlantic beaches and ice cream shops - where he stood in line with other customers - so much that he came every summer of his presidency but one. Now on his sixth summer visit, Obama may well match that record.
"If the motorcade is going by I'll stop and watch," said Thomas Dresser, a year-round resident and author of several books about the Vineyard. "But we're not racing down the street every time we hear he's headed to the golf course."
Since arriving by helicopter last weekend, Obama's schedule has included a familiar mix of mornings with his family and afternoons on one of the island's golf courses with his buddies, including summer resident and comic Larry David.
It's easy to stay connected to Washington at the spacious beachfront compound the Obamas have rented on the island's north shore, which faces the placid Vineyard Sound and not the unruly Atlantic.
National Security Advisor
A series of TV and radio interviews taped just before he left Washington, along with a letter to the editor in the New York Times about the Voting Rights Act, have kept up a light presidential presence on the news. But barring a sudden crisis, the White House warned weeks ago that Obama planned no public events during his holiday.
It's the remote nature of the Vineyard – most people come on a 45-minute ferry from Cape Cod or by air – that has drawn presidents over the years.
Grant learned of it during the Civil War, when two Vineyard ferries were conscripted into the Union Navy. Years later, in 1874, he came as president and stayed in a rustic cottage in the Methodist Wesleyan Grove Campground. The gingerbread cottages still draw tourists to Oak Bluffs, one of six towns on the island.
Grant "put the Vineyard on the map, and it became a place where tourists would go," said Dresser, author of "Martha's Vineyard, a History" and a local historian. "Having the president choose the place kind of drew the national attention, just as it does today."
Franklin D. Roosevelt headed here in August 1941, telling reporters he needed to get away from the heat in Washington.
Instead he sneaked off the presidential yacht and onto a Navy heavy cruiser, the Augusta, in the waters off Menemsha, one of the six Vineyard towns, and sailed in secret to Newfoundland, Canada, to meet British Prime Minister Winston Churchill, who arrived on his own warship
It was at that summit, even before the Pearl Harbor attacks brought the U.S. into the war, when they forged the principles of the Atlantic Charter, a policy statement that set Allied goals for the postwar world.
Although President Kennedy maintained a family compound in Hyannis, across the sound on Cape Cod, he liked to sail near the Vineyard. His widow, Jacqueline Kennedy, later bought a remote 377-acre property along the windswept Atlantic dunes along Moshup's Trail, in the westernmost part of the island.
Her daughter, Caroline Kennedy, the U.S. ambassador to Japan, has put several parcels of the property up for sale, but has kept most of the pristine property from development.
Since then, the Vineyard has mostly drawn Democratic presidents, not a great surprise since Massachusetts remains among the most reliably blue of states in presidential elections.
Ronald Reagan preferred chopping wood at his ranch in the mountains north of Santa Barbara. George H.W. Bush raced speedboats at his family compound on the rugged, rocky coast in Kennebunkport, Maine.
His son, George W. Bush, preferred the wilting heat of his ranch in Crawford, Texas. "Most Americans don't sit in Martha's Vineyard, swilling white wine," he famously said there in 2002.
That appeared a jab at the Clintons, who had revived Martha's Vineyard as a presidential retreat. The president enjoyed sitting in with musical bands, visiting the yearly agricultural fair and browsing the bookstores.
"It became sort of blasé," said Dresser. "You would say, 'Okay, here comes the president walking down the street. Again.' It became more or less common."
Obama is the beneficiary of that familiarity. Close advisors say he appreciates the chance to blend in, at least a little. But compared to Clinton, he spends little time in public.
The Obamas stay on a Chilmark property large enough that they don't have to leave it to go biking and hiking.
They stayed one summer at a compound that faces the Atlantic, but changed locales after neighbors complained about a five-mile detour the Secret Service imposed on local traffic while they were there. They spent the first few years at another property, but it was sold and the new owner took it off the rental market.
Whoever sits in the Oval Office, the annual summer relocation of the White House calls for a "significant footprint of infrastructure," as Obama deputy press secretary Eric Schultz puts it, listing the staff, secure phone lines and mysterious "national security equipment" among the things that get transported.
"But mostly we try," Schultz said, "to let the president have some down time in the middle of August."
So far, the Obamas have gone out for dinner twice, to the locally sourced State Road restaurant in West Tisbury and, on Wednesday, to Alchemy in Edgartown.
When their daughters were younger, they made at least one run as a family to get ice cream, but public outings with their teenagers are fewer and farther between now.
Neighbors say they think the Obamas should get out on the town every once in a while, just like everyone else here.
They may not stand in line for a glimpse of the president, but they don't mind the "personal and politically symbolic importance" of their annual visitor, said Peter Oberfest, a longtime resident and publisher of the Martha's Vineyard Times.
"Most of us are generally sympathetic and simply like these presidents, and we enjoy our proximity to them and their families," he said.