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Good question, I have never shopped locally much when we lived in Brooklyn, but once we moved to Long Island, I have discovered pleasure in buying certain things locally (Oceanside)
Butcher (U need a prime meats)-I used to think that those who bought meat at the butcher were just spoiled, but once I tasted the difference, I was hooked, and on many cuts, the prices are competitive with supermarket and even Costco, the staples like chicken breasts are $1.99 year-round.
Bakery-Whistle Stop desserts cheesecakes are to die for
Seafood and fish-Freeport
Hair, butcher, local farmstand, bakery, liquor store, Chinese/Pizza/Noodle house. Jeweler, bicycle shop, silk screen guy, gift shop. Strathmore bagels is a chain, so I don't know how 'local' that would be considered even though they do support local events. I occasionally use the local mechanic, but my main guy is in Centereach.
I forgot to add that many things -- like our 3 locally owned hardware stores -- went under when Home Depot came to town a dozen or so years back. Sweezy's is gone, too.