8.5 out of 10

Oyster Bay

40.8636800510778 -73.5322888421565
Great for
  • Eating Out
  • Neighborly Spirit
  • Parks & Recreation
  • Clean & Green
  • Peace & Quiet
Not great for
  • Public Transport
  • Nightlife
  • Lack of Traffic
  • Medical Facilities
  • Pest Free
Who lives here?
  • Professionals
  • Singles
  • Families with kids
  • Retirees
  • Tourists


5/5 rating details
  • Neighborly Spirit 5/5
  • Clean & Green 5/5
  • Peace & Quiet 5/5
  • Eating Out 4/5
  • Nightlife 1/5
  • Parks & Recreation 5/5
  • Shopping Options 2/5
  • Gym & Fitness 3/5
  • Public Transport 1/5

"A hamlet with an old-town vibe...in a good way"

Love this town! Many options in terms of housing: co-ops, townhomes and fabulous period homes, as well as beautiful new construction. If you're the outdoorsy type, you can swim in the bay, kayak or boat out of the Oyster Bay harbor. There is a great town park by the water with various playgrounds for children of all ages, as well as public tennis courts. Teddy Roosevelt's summer home is here, as well as a bird sanctuary offering many programs for children and adults. The main street has an 'old town' charm and is lined with pretty old churches and an array of eclectic little shops and galleries, as well as an old fashion ice cream shoppe.
In the summer the town is alive with foot traffic and on Thursday nights the vintage car owners display their cars for all for all to enjoy. On occasion you might catch sight of one its many famous residents, like Billy Joel, at the local pizza parlor.
The second week in October, the Oktoberfest brings many people from outside of the area and it can be fun if you like crowds.
  • good restaurants
  • beautiful
  • great place to grow up
  • quiet
3/5 rating details
  • Neighborly Spirit 3/5
  • Safe & Sound 4/5
  • Clean & Green 5/5
  • Pest Free 4/5
  • Peace & Quiet 5/5
  • Eating Out 4/5
  • Nightlife 2/5
  • Parks & Recreation 4/5
  • Shopping Options 2/5
  • Gym & Fitness 2/5
  • Internet Access 5/5
  • Lack of Traffic 4/5
  • Parking 5/5
  • Resale or Rental Value 5/5
  • Medical Facilities 4/5
  • Schools 3/5
  • Childcare 5/5

"Lots o' Yachts"

Embarrassingly enough, even though I grew up in Oyster Bay Cove, I didn’t know until just now that the Town of Oyster Bay encompasses almost 170 square miles, includes 18 villages and 18 unincorporated hamlets, extends from the Long Island Sound on its northern border to the Atlantic Ocean on its southern, and is home to 293,214 people. And here I thought every small village was its own island, and that my hometown consisted of a couple hundred families.

Since 36 villages and hamlets are too much for one review, I’ll stick to the hamlet of Oyster Bay (population 6,707), which has a post office, a train station, stores, restaurants, and museums; Oyster Bay Cove, which, except for an Audubon Center, is purely residential; and Cove Neck, residential except for Sagamore Hill, former home of Theodore Roosevelt, now a museum and historic site.

This is serious sailing/riding country, and its backbone population remains old-money WASP. Traditionally Republican territory, Obama beat McCain here in Nassau County in 2008, I’m sure because residents are only fiscally Republican; no one would dream of trying to legislate any sort of personal behavior laws, as that would be rude.

Social lives revolve around clubs – yacht clubs, beach clubs, golf clubs, some of which are so private you can’t even get onto their website without a password. Here dress codes and behavioral issues are strictly enforced; cellphones are forbidden, and, according to one club’s by-laws, “women are allowed to wear a shirt without a collar or without sleeves, but may not wear a shirt without sleeves and a collar” (translation: no tank tops.) One club only began allowing women into their bar area in the early 1980’s. Notice I am not mentioning any proper names, as that would entail name-dropping, which would also be rude.

That said, this is a truly beautiful area. Located right on the Long Island Sound, it is a sailor’s dream, with sweeping vistas of blue skies and distant yachts flying multi-colored spinnakers. As long as there is wind and open water, people will sail; frostbiters continue into November, and a family friend used to don a drysuit and go windsurfing in December until he was nearly 80. People are protective of their paradise and the zoning laws are fierce; whenever another grand old estate bites the dust, land trusts and nature groups rush to preserve at least parts of it, and set-back laws prevent the cheesier types of brand-new McMansions from being built right alongside the main road.

The public schools here are part of the Oyster Bay-East Norwich Central School District, which includes Oyster Bay (hamlet), East Norwich, Oyster Bay Cove, Cove Neck, Centre Island, as well as parts of Upper Brookville, Muttontown, Laurel Hollow, and Mill Neck. Kids go to the Theodore Roosevelt Elementary School (K-2), the James H. Vernon Middle School (3-6) and the Oyster Bay High School (7-12.) The schools here are fairly good; US News ranks Oyster Bay High School as 64th within New York. Many people prefer to send their kids either to a private day school (East Woods, Friends Academy, Portledge, Green Vale, St. Dominic’s) or to boarding school.

What is there to do? This place is rich in history, and there are several restored circa-1700’s houses which have been turned into museums right in town: the Townsend Museum, Raynham Hall, and the Earle-Wightman House, and are all worth a look. There’s the Oyster Bay Railroad Museum, which is open now even as they expand to include more exhibits and displays. Right along Oyster Bay Harbor is the Waterfront Center, a fantastic marine environment education center, where you can learn to sail, swim, take certification classes, rent boats and kayaks, go fishing, or sail on Christeen, a National Landmark and the oldest Oyster Sloop in North America.

The Department of Community and Youth Services offers all kinds of workshops, concerts, art programs, pre-schools, and programs for children, adults, senior citizens, veterans, the handicapped and disabled. They oversee many centers, including the Community Center on Church Street.

Every Tuesday night from May through September the town shuts down Audrey Avenue, provides live music, and hosts Cruise Night, where anyone with an awesome car or motorcycle can show it off. It’s advertised as “from radical to rat-rods, Duesenbergs to Ducatis!” Who could resist?

Oyster Bay hamlet is home to a fine array of restaurants (with several oyster bars, naturally), as well as supply stores, shops, bakeries, and even two spas. Appallingly enough, Oyster Bay now has a McDonald’s, though at least it’s been relegated to an out-of-sight spot on the road leading away from town.

If you’re into hiking and natural beauty, there are no shortage of preserves and refuges around Oyster Bay and the Cove, including the 3,000-acre Oyster Bay National Wildlife Refuge, home of New York State’s only remaining commercial oyster farm. Several beautiful old estates have been preserved as museums, parks, botanical gardens, and event venues; definitely check out Coe Hall/Planting Fields Arboretum, C.W. Post Community Arboretum (in Brookville), and Bailey Arboretum (in Lattingtown).

Oyster Bay Cove is home to the Theodore Roosevelt Sanctuary and Audubon Center, the first Audubon songbird sanctuary in the country, which provides all kinds of education programs for children and adults. Continue into Cove Neck and eventually you’ll find Sagamore Hill, the former President’s “Summer White House” and home until his death in 1919. I can still remember walking through the front door during an elementary school class trip and being traumatized by the sight of all the gorgeous exotic animals he had slaughtered and stuffed, and who filled the building like props from a medieval house of horrors.

Oyster Bay is the last stop on the Oyster Bay Branch of the Long Island Rail Road, although some residents prefer to drive to neighboring Syosset and take a quicker and more direct train from there into Manhattan. You can drive here on the infamous Long Island Expressway, where they still seem to be working on the same sections of road they were working on 40 years ago. LaGuardia Airport, in Queens, is 19 miles away.

There are seven colleges within 14 miles, including Hofstra and Adelphi; and three hospitals within 10 miles. Oyster Bay has had its share of celebrities, including Typhoid Mary, who was discovered working as a cook in a summer house here in 1906.

The median income for a household is $79,802; median house value, $605,552; and median rent, $1,586.
  • beautiful
  • quiet
  • great place to grow up
  • very expensive
  • not even slightly diverse
  • can make you want to flee
Recommended for
  • Professionals
  • Singles
  • Families with kids
  • Retirees
  • Tourists
  • LGBT+
  • Country Lovers
  • Trendy & Stylish
  • Beach Lovers

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