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Oyster Bay, Long Island - Walking and Driving Tour of Oyster Bay

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Oyster Bay, Long Island - Walking and Driving Tour of Oyster Bay
Welcome to Oyster Bay

One of many posters welcoming visitors to Oyster Bay

Photo © Linda Tagliaferro
Located on the North Shore of Nassau County, Oyster Bay was originally home to the Matinecock Indians. When the Dutch settled there in the 17th century, they named the area for the rich beds of shellfish that flourished in the surrounding waters. Within the Town of Oyster Bay, which encompasses a number of villages, the hamlet of Oyster Bay is famed as the former home of Theodore Roosevelt, the only U.S. president to hail from Long Island.

There's much to see in Oyster Bay, so take a leisurely walking and driving tour of this charming place with its quaint streets, historic houses and many reminders of the 26th president, including Sagamore Hill, known as Theodore Roosevelt's "Summer White House."

Give yourself a few hours to take in the sights and step back in time to an era when this quiet community on the water was the favorite place of our 26th president. If you'd like a longer, self-guided audio tour of 30 historic sites in downtown Oyster Bay, stop by the Baykery Café at 124 South Street for a listening device that gives background info on the sites that you'll see. The long audio tour is free when you make a $5 purchase at the café. Or follow this shorter, but equally pleasant itinerary.

In the summer, don't miss Oyster Bay FREE Summer Concerts & Movies. And every year, there's the FREE Fourth of July at Sagamore Hill, replete with a live band playing patriotic music on the porch and a visit from "President Roosevelt" in the form of an actor who's a dead ringer for the former commander-in-chief.

If you're visiting in October, be sure to check out the annual Oyster Festival on the Waterfront at Theodore Roosevelt Park.

And celebrity watchers: take note. It was reported that Brad Pitt and Angelina Jolie shopped in Oyster Bay's supermarket when they rented a house in Lloyd Neck.

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