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Exit Three on the LI Sound, Oyster Bay

Captains and families on the Long Island Sound do not have to go far for a fun weekend on their boat. Long Island’s north shore has six “exits” off the Long Island Sound that are worth a visit. These include three bays, two harbors and an inlet.

At these six north shore ports of call, you will find boutiques, bars, micro-breweries, entertainment and good food. Some have museums and historical walking tours. If you just want peace and quiet, there is always a place in the bay where you can throw the hook and be alone. During some of our visits, we would combine the best of town offerings with the solitude of the bay by splitting a couple of night’s dockside and another night or two at anchor.

Oyster Bay is part three on Long Island’s North Shore places to play.

Oyster Bay lies between Hempstead Harbor and Huntington Bay. It is also directly opposite Stamford, Connecticut. Oyster Bay is an unusually shaped harbor and a perfect duck and cover port in the event of bad weather due to its good protection from seas.

Cold Springs Harbor
It offers two areas to visit. When entering the harbor it is about three miles south towards Cold Spring Harbor. Heading this way will give you a nice ride along the shore where you can admire the homes.
Eventually, you will reach a sand spit that has a narrow pass so watch your markers and depths. If you motor carefully past the spit you will see to the west the campus of the famous Cold Spring Harbor Laboratories where people from all over the world work on curing different diseases. This area is crowded with moored boats so anchoring here is not desirable. Instead, anchor north of the spit or call Powles Marina (631-367-7670) to see if they have any moorings available.
Cold Spring Harbor is a village worth strolling around and only a five-minute walk up to a quarter-mile Main Street. Here where you will find boutiques, food and ice cream. The closest restaurant to the water is Mist Harbor. They have a well-rounded menu. Favorites here are the Pork Chop Michelle, power ball salad and the panko-crusted flounder sandwich.
For kids and interested adults visit the quaint firehouse museum in the village or the small Whaling Museum on the far side of town. I also recommend getting your shore legs back with a 10-minute walk south to the Cold Springs Harbor Hatchery. Here you can fish for trout or feed them with pellets. (Fun Fact: Billy Joel’s first album is named after the village)

Sagamore Hill
Heading north from Cold Spring Harbor keep Cove Neck on your port. At a little past halfway up Cove Neck, you will see an inlet. Just north of this is Sagamore Hill, the home of President Theodore Roosevelt from 1887 to 1919. This is a must-see place and I recommend you throw the hook and dinghy to the beach. From the beach, it is about a three-quarter-mile walk to the visitor’s center and this magnificent and totally restored Queen Ann-style home.
The National Parks Service offers an excellent tour of the house where you will see its original furnishings and his hunting trophies. The 26th President died in his sleep here in 1917 and part of the tour includes seeing the bed and bedroom. The grounds include a museum in a former mansion where General Theodore Roosevelt Jr lived. To see what is open, visit If you cannot get on a tour the grounds and home are worth a visit.

Continuing your cruise of Oyster Bay from Cove Neck, turn to port at the end. Watch your markers and wake signs from here and into the rest of Oyster Bay. Off to starboard is the Seawanhaka Corinthian Yacht Club. This yacht club opened in 1871 and is one of the oldest in the United States. It was written about in Nelson DeMille’s book The Gate House. The yacht club allows members of reciprocal clubs to stop by for lunch or dinner. They have a Sunday evening “Salty Dog” outdoor BBQ’s that we have enjoyed. You can rent a mooring ball for the night but it can get a little bouncy from the morning fisherman and passing boats.
Continuing into Oyster Bay you will see to the south a protected area called The Cove. While this is a pretty place to stop I prefer to anchor in West Bay. Moving along and past Moses Point on Center Island, you will see the Oyster Bay Marine Center Sagamore Yacht Club and the Town of Oyster Bay Marina to the south. There is no room for anchoring in this area. Sagamore Yacht Club, (516 922-0555), has 15 balls they rent.
The Oyster Bay Marine Center, (516 624-2400), also rents balls and sometimes slips.
When docked or moored in the southern part of the bay you are only a 10-minute walk to the village. Oyster Bay is a historical town with a few good restaurants. For history buffs you can visit an original “Washington Spy Ring” home called the Raynham House built in 1740. ( This was the residence of Robert Townsend, one of George Washington’s spies. Another place to visit is Billy Joel’s motorcycle museum called 20th Century Cycles. Here you can see dozens of bikes restored or reworked that are owned by the piano man. For information go to

Center Island West
No captain will find a more peaceful evening than staying on the hook in West Bay. To get here you pass the southeast tip of Center Island (where you can see Billy Joel’s mansion) and continue north. This area west of Center Island is called West Harbor. Here you are completely protected from rough seas on all sides. On weekends this area has many boats and rafting parties but the bay is large enough to keep your distance. At night I have never seen more than several boats anchored out. The average depth in this area is about 8 feet with a good hold. The best part of being at anchor here is the solitude, safety and stars.
A side note about Oyster Bay that should be noted and avoided is called the Sand Hole. This pretty and protected little anchorage at the tip of Lloyd Neck is a nasty place to get in and out of. It should be attempted at high tide only and if you are with someone who knows the water. Each year boats get damaged entering it. Once you are inside you have little maneuvering room if a storm blows. I have had friends play bumper boats in the hole or get grounded in a sudden storm. Explore this place in a small boat or dinghy.
For complete information on what Oyster Bay offers go to
For copies of the first two Long Island Sound exit stories email Capt Tab Hauser of at

Tab Hauser has been a contributor to L.I. Boating World for 10 years. He is also a travel writer on national, international and expedition-style travel when not boating.