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

Welcome to Oyster Bay

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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The Baykery Café in Oyster Bay

Baykery Café
Photo © Linda Tagliaferro

A good place to start your walking and driving tour of Oyster Bay is at the Baykery Café at 124 South Street. Their menu reads, "Breakfast served all day. No punishment for late sleepers." So don't worry if you're in the mood for a large morning meal during the middle of the day!

The Baykery Café serves sandwiches, salads, omelettes and more in a quiet, intimate space frequented by locals. If you have a sweet tooth, you're in luck. The Baykery Café offers a wide variety of desserts including luscious brownies, tempting raspberry bars, chewy oatmeal raisin cookies and much more.

If you'd like to lounge for a while, order a Danish or apple pie, a cappuccino or a glass of freshly-squeezed orange juice, and read a book in the cozy little library in the back of the café.

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Snouder's Drug Store in Oyster Bay

Snouder's Drug Store on South Street, Oyster Bay
Photo © Linda Tagliaferro

After you've had breakfast, lunch or a quick snack at the Baykery Café, take a short walk to Snouder's Drug Store, a landmarked building at 108 South Street at the corner of West Main Street. This historic building is the oldest continuously-run business in all of Oyster Bay. A pharmacist named Abel Miller Conklin opened an earlier drug store somewhere in Oyster Bay, but all records of its location have unfortunately been lost.

What is known is that in 1884, Conklin moved his drug store to its present location. He unfortunately passed away soon after the move, and his son-in-law, Andrew Snouder, continued the family-run business, and in 1900, the name was changed to Snouder's Drug Store. The business continues to this day.

In 1887, Snouder's was also the first place in Oyster Bay to install a telephone.

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Raynham Hall Museum

Raynham Hall Museum, Oyster Bay
Photo © Linda Tagliaferro

Walk down the block until you come to 20 West Main Street, where you'll find the Raynham Hall Museum. The historic home's legacy includes ghost stories and true tales of spies.

Samuel Townsend, a Quaker and a well-to-do merchant, made his living by importing items like tea, spices, wine, rum and pottery in his four ships. The vessels sailed to the Caribbean, Europe and South America. In 1738, Townsend bought the property that is now a museum. It originally had four rooms, but as Townsend's family grew to include his eight children with his wife, Sarah, they added more rooms.

During the American Revolution, Townsend's house became the headquarters for the British under Lieutenant Colonel John Graves Simcoe for a period of six months from 1778-1779. One of Simcoe's frequent visitors was the British Major John Andre. Legend has it that Townsend's daughter Sally overheard the two men discussing Benedict Arnold's plot to surrender the fort at West Point to the British. She immediately alerted her brother, Robert, who was in a secret group called the Culper Spy Ring. He passed this information over to then General George Washington and the plot was foiled. Benedict Arnold escaped, but Major John Andre was captured and hanged.

Ghost stories have long swirled about Raynham Hall. From strange noises in the night to a spectral lady who slowly strolls through the house at night, weird and unusual tales about this historic house abound.

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Wild Honey Restaurant

Wild Honey Restaurant in the historic Moore Building, Oyster Bay
Photo © Linda Tagliaferro

Take a short walk over to 1 East Main Street. There, you'll see a beautiful Queen Anne-style structure, the Moore Building, now on the National Register of Historic Places. The ground floor of the building is occupied by a great place for lunch or dinner, Wild Honey Restaurant, which serves up delicious food with a side of history.

Originally built as a small grocery store in 1891, the building was expanded by its owner, James Moore, in 1901. The expansion included upper floors that could be used for public meetings. In 1903, president Theodore Roosevelt, who lived in nearby Sagamore Hill, a.k.a. "The Summer White House," during the warmer months, made this building famous when his secretary, William Loeb, conducted meetings on the upper floors.

There was even a telephone and telegraph line to Sagamore Hill and the White House in Washington, D.C., set up from the Moore Building.

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First Presbyterian Church of Oyster Bay

The First Presbyterian Church, Oyster Bay
Photo © Linda Tagliaferro

Take a short walk to 60 East Main Street. There, you'll find the boyhood church of Theodore Roosevelt and his family, the First Presbyterian church of Oyster Bay, perched on a grassy hill. Completed in 1873, this church was built in the "Stick Style" or "Carpenter Gothic" style of architecture.

As a young architect embarking on his career, J. Cleveland Cady designed the church. Cady later became famous as the architect of the American Museum of Natural History, the original Metropolitan Opera House, 23 other churches, and other buildings.

When Theodore Roosevelt, Sr., passed away, his son ---the future president--- attended his father's funeral at this church. Today, the building is listed on the National Register of Historic Places.

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Stroll the Beach on Oyster Bay

The beach at Oyster Bay
Photo © Linda Tagliaferro

Continue strolling down East Main Street, window shopping or stopping for a snack, or just hop in your car and take a short ride to the beach. Breathe in the salt air, enjoy the sunshine and watch sailboats gently gliding off into the distance in lovely Oyster Bay.

There's a Waterfront Center here, and this non-profit organization aims to get people out on the water. The center offers summer programs for children, summer sailing programs for adults, kayak and sailboat rentals and more.

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The Nantucket Lightship, Oyster Bay

The Nantucket Lightship
Photo © Linda Tagliaferro

Looking out at the bay, you'll see a majestic ship, the historic Nantucket Lightship, docked at the Jakobson Pier on the western waterfront of Oyster Bay.

Of the 12 such vessels that served for many years at the Nantucket Shoals Station, Massachusetts, the Nantucket Lightship LV 112 guided ships with its beams of light from 1935 to 1942. In its long history, the Nantucket survived two hurricanes, visited many ports and was once a floating museum in Maine.

In 1993, the Intrepid Air-Sea-Space Museum in New York City acquired the 148-foot lightship, and later donated the vessel to the H.M.S. Rose Foundation in Connecticut.

Later on, Staten Island's National Lighthouse Museum, hoping to open soon, purchased the Nantucket for $1. However, today, no one knows if the museum will ever open because of its financial difficulties. In 2004, the historic lightship was towed to Oyster Bay, and was only intended to stay there for a short while to be restored. However, the Nantucket has remained docked in the bay ever since.

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Sagamore Hill

Sagamore Hill
Photo © Linda Tagliaferro

Now that you've seen a number of sights in the hamlet of Oyster Bay, hop in your car to continue your tour of Theodore Roosevelt's beloved landscapes. Drive down East Main Street, which becomes Cove Neck Road, and continue for about two-and-a-half miles outside of town. You'll soon find Sagamore Hill. The 26th U.S. president lived there from 1885, and passed away in his bedroom in 1919. The day before he died, he told his wife, "I wonder if you will ever know how I love Sagamore Hill."

While still engaged to Alice Hathaway Lee, a young Theodore Roosevelt bought property on a hill on Cove Neck. He had planned to build a house there for himself and Alice. But after their marriage, Alice died just two days after giving birth to their daughter, and sadly, Roosevelt's mother died on the same day. He wanted a house that would provide a good home for his daughter, so he hired architects to design one for the property. In 1885, the sprawling Victorian house was completed, and Roosevelt moved in, together with his sister, who offered to take care of the baby.

Years later, Roosevelt married a childhood friend, Edith Kermit Carow, and three of their children, Theodore Jr., Kermit and Ethel were born in the house. From 1902 till 1909, then president Theodore Roosevelt conducted his business here each summer, and the house became known as "The Summer White House." The 23-room house and its surrounding natural beauty is now a National Historic Site.

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