You can go to pretty much any Long Island seafood restaurant and sample oysters and lobster any time of year However, there are reasonable prices and expense account prices. For a bargain on lobster, head to Port Jefferson and go to a not so fancy but popular seafood spot called The Steam Room. They offer a lobster dinner for $17.95. Again, it's no frills but it's lobster which is pretty hard to screw up. You can sample oysters there too. In Riverhead, you have Tweeds where you can try oysters but will come at a more expensive tab. For more casual in the Riverhead area, there's Lobsterroll Northside in Baiting Hollow. Hope this helps and enjoy the lobster and oysters!
I don't know of any great seafood restaurants in Riverhead. You'd be better either heading to the Hamptons or the North Fork of Long Island or have it while you're in NYC. The Oyster Bar in Grand Central Terminal in Manhattan is an iconic place to have oysters. There are also some good seafood places in the city like Mermaid Inn, Jack's Luxury Oyster Bar and Mary's Fish Camp. Details on
On the North Fork in Greenport, Claudio's is popular although I don't think it's all that good.
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