Shelter Island is only going to be a five mile trip so again no need to hurry or go fast. I took Frank to shore in the morning and had to stop back to Grindstone. It was quite busy and the line was out the door due to spacing requirements, but Frank was fine with it. When it was finally my turn to go in I tied him up to a tree outside the door. He was cool and patient but gave me a funny look when I was coming out and another guest was entering with his dog. I guess dogs are allowed- good to know. We took the donuts back and had some with coffee before pulling anchor. The trip only took us less than an hour. We had read about the anchorage and it was clear you must stay within the marked area or the local harbormaster will come yell at you and tell you to move. The anchorage was clearly marked and there were several boats already there but there was plenty of room. We anchored as close to a small island of sorts- at low tide it has a piece of land that connects to the mainland, but at high tide it is an island- this is called a tombolo. and is named Taylor’s Island. It is named after S. Gregory Taylor, a successful hotel owner who donated the land and cabin to the town of Shelter Island.. This little tombolo turned out to be a great little retreat for Frank as we were docked near a nature preserve that did not allow dogs. The wind was picking up and rain was expected. We battened down the hatches and waited for the storm to pass. Eventually it let up enough to take Frank to the island and we explored the house and grounds. More research was done about the town and tombolo as we settled in for the evening feeling secure.
Day 2- “Shelter Island was purchased by Nathaniel Sylvester in 1652. He built a house for his 17-year-old bride, Grissel Brinley of London, and they became the first European settlers. The native Manhanssets, long-time residents when the Europeans arrived, called the Island Manhansack-aha-quash-awamock, meaning “island sheltered by islands.” After breakfast and coffee we took the dinghy and bikes about a mile and half to the town dinghy dock. We unloaded and set off to explore. We found a brewery that was open: Shelter Island Craft Brewery. The ride there was interesting, especially with no brakes on the bikes. We are now into an area with lots of hills so it’s sometimes a gamble on the downhill portion. Lauren has gotten pretty good at using her feet to slow her down, where I just go full on forward as a scout and hope for the best. We also passed a house that was selling oysters out of their garage but we weren’t brave enough to stop for those. We discussed it after some beers, but keeping them cold for our ride back probably wasn’t going to work out so well and we weren’t in the mood for a game of intestinal roulette. We were hungry though so we found a pizza joint: Shelter Island Slice where we shared a few slices of pizza pie. Bellies full and feeling good we made our somewhat harrowing ride down the hills back to the dock and loaded up the bikes to retreat back to Klondike. We looked at our options and decided Montauk will be our next stop in this area, but looking forward we are now discussing Rhode Island and maybe Massachusetts as we still have plenty of time before we have to start heading back to New York…