trishlaplaca 
Original Post November 6, 2022
While Block Island tested both Oyster’s and our mettle, the next cruise and stay to Greenport, Long Island turned out to be an absolute delight. Neither Jeff nor I had even heard of Greenport, an olde New England tourist village located on what’s known as the North Fork of Long Island. Across the way on the southern tip is well known Montauk, but according to our navigational guides we suspected that here could be an even sweeter spot to be able to settle in for the night. We planned to travel across the Long Island Sound and then up the Connecticut River where Oyster would be stored for the winter the next day.
The sun shone brightly and we cruised easily, but despite the glory of the day both Jeff and I grew unusually quiet and pensive. We were both feeling the same way: we’d come to adore this new nautical life and our Oyster – choppy waters and all. Yes, we were novice sailors with plenty more to learn, but it all felt all so right. The thought that we’d have to give it all up within days seemed inconceivable.
By mid afternoon we approached tiny Greenport. We eased our way through a narrow inlet between a row of condos and homes to our left (port side!) and a small harbor to the right. We had just gotten the okay by phone to dock at the Wayside Inn’s private docks. The good news was that there would be several slips to choose from since high season ended that very weekend. The bad news was that that meant that there’d likely be no one to assist us by taking the ropes to help tie us up to the dock. Jeff hadn’t yet had to back into a slip before – especially between the two million dollar boats we’d have to squeeze in between. Talk about pressure.
Once Jeff remembered that we had a handy bow thruster to help maneuver the boat from side to side, he set us in like a charm. We tied up and went into the quaint Wayside Inn to check in. All was quiet, yet even after what must have been a wildly crazy tourist season, the woman at the desk couldn’t have been more helpful. We settled in and followed her instructions to head toward Main Street where we’d find a few remaining cute shops and restaurants open. Greenport is truly charming, filled with pretty circa 1800’s gingerbread homes and churches. Jeff and I then proceeded to the dockside restaurant for afternoon cocktails. It was fun getting swept up into the town’s positive energy without having to dodge teems of fellow tourists on the streets.
The next morning we savored breakfast in a homey diner, toured a classic boat restoration workshop, and checked out Preston’s, an old store with creaky floors and all things nautical before getting underway towards Connecticut. Goodbye, Greensport. We’ll remember you fondly!
