..Rode a boy with a 6 gun in his Hand... From Billy Joel's Ballade of Billy the Kid.
Oyster Bay is an interesting little town on the North Shore of Long Island. There's a beach and some historical sights, what more could you want? It's not a bad little place to spend the day if you want to see a smaller town on Long Island that isn't too suburbanized. While there is some strip malls, they hold a lot of the necessary places - grocery store, drug store, Dunkin Donuts. You wont find large box stores here, and there is a small downtown district so it has a quaint feel to it. And if you're looking for stars, go to Stop and Shop and maybe Branjolina will show up.
I'll start with some historical sites: Teddy Roosevelt's house, Sagamore Hill is in Oyster Bay Cove, it's a very nice National Historic Site. Visiting the house is by tour only, which are conducted regularly throughout the day and only cost $5. Check their website for operating hours. If you're stuck waiting for your tour there are a few other things to do there - take a walk, Sagamore Hill is in a lovely woody area and walking paths. There is also another museum on the property about Teddy. Of interest in Oyster Bay is the talk of building a Theodore Roosevelt museum in Oyster Bay, though I'm not sure of the status of it.
Raynham Hall is another museum in Oyster Bay. Raynham Hall is the former home of the Townsend family and features the history of the American Revolution and Victorian Times. There is also a Railroad museum in the works for the town.
The beach. Oyster Bay has a quaint little beach, it has a view of Centre Island and its mansions, always fun to look at. There are tennis courts, handball courts, a playground for children and the Oyster Bay marina with some lovely boats to look at. I enjoy taking a walk at the beach when I'm in the area. The one problem with the beach is that it is VERY rocky. If you're not interested in going in the water you're better off hanging out at a grassy area and avoiding the rocky sand. If you need to park and don't want to pay the fee, there is some parking near the old train station at the end of Audrey Avenue.
There are no hotels in Oyster Bay, the closest one would be in East Norwich, but I believe it is closing if it hasn't already.
Dining - For a diner type of restaurant I recommend Taby's on Main Street. The prices are reasonable, better then many other diners on Long Island, the portions large and the food is fresh and consistently very good. There is also Canterbury Ales which is popular with the locals. They have a bar and are a little pricier. Oyster Bay Clam Bar has a good reputation though I've never eaten there. If you want some quick pizza or pasta you can try Mario's, I don't love their pizza, but the have fantastic ravioli.