Jamesport takes its name from a man who tried and failed to establish the area as a commercial wharf for shipping and whaling. But though excessively low tides foiled James Tuthill in the 1800s, his namesake hamlet has flourished. Tuthill also wasn’t entirely off-base with his aquatic-focused vision: Once people started traveling across the North Fork on the LIRR, Jamesport became a happening spot for fishing. The hamlet’s history also dates to 1731 with the Jamesport Meeting House; two stories and bell tower-topped, it stands as the oldest public building in Suffolk County. Presently, Jamesport quite captures the spirit that defines the North Fork. There are the Cape Cod-style homes and serene beaches, but mostly it’s in the wine. With reds, whites, rosés, and even oranges at numerous vineyards, you’ll find plenty of options to sip on as you kick your feet up and stay awhile.