Mamaroneck, NY to Milford, CT

Mamaroneck, NY to Milford, CT


We departed Mamaroneck at 0830 under power as winds were less than 5 knots. We raised the main sail at about 1030 and sailed along at a leasurely 3 to 4 knots. We motor sailed for about an hour in mid-afternoon to charge our batteries and increase our speed.  We anchored behind Charles Island near Milford at 1700. Shortly afterward, a fleet of sailboats began flowing out of Milford Harbor for races. About 20 boats participated in a triangular course of about 4 miles in length. It looked like 3 fleets raced: small boats with spinnaker, large boats with spinnaker, and large boats main and jib. The winds were perfect for a fun race with good speed.

Charles Island is not very large and surrounded by rocks. "The Bar" reaches out to the island from Myrtle Beach and may be under a foot of water at most at high tide. The charts label the bottom as "Foul" for about 500 feet out from "The Bar" and Charles Island. However, reports on Active Captain are that this is a good anchorage in fairly settled conditions provided you stay in depths of 10 or more feet. This proved to be the correct and we had a quiet night with two other boats anchored near us.

Bill and Amy - Full Circle

Bill and Amy - Full Circle


We drove to Stamford in the morning to meet Bill and Amy of Full Circle for lunch at the Crab Shell Restaurant. They went south with us on the SAIL ICW Rally and crossed over to the Bahamas for the winter. We last saw them at Solomons Island on the Chesapeake as we were all heading north up the Bay. Their home port is Stratford, CT. Bill and Dwayne went over charts and discussed places to visit on Long Islaned Sound. Amy got Carla excited with talk of the Bahamas and how wonderful it was to have made the trip. We had a great lunch and look forward to our next get together which will probably on Foreign Affair's southbound journey toward the end of summer.

Oyster Bay

Oyster Bay


We slept well as the anchor dug deep upon set and we laid out most of our chain. The bluff protecting the anchorage cut down the wind and there was barely a ripple on the water. We were awaken around 0600 when the oyster dredgers began their work. This was the first time we saw oyster men working their trade. Three smaller dredgers were making loops around their beds marked with stakes. One large dredger was working further back in the bay and we were amazed at how many oysters she was hauling on board using her conveyor belt system. About a dozen small boats with one or two men aboard were hand tonging. It was amazing as the tongers would bring up a bushel at a time and the large dredger appeared to bring up the equivalent of a tonger's boatload in a matter of minutes. It is no wonder the oyster beds were depleted so quickly with the advent of mechanized dredging. The beds are now assigned to individuals or corporations and managed to maintain a sustainable supply of oysters.

Measured for New Sails and Explored Hempstead Bay and Oyster Bay

Measured for New Sails and Explored Hempstead Bay and Oyster Bay


Jamie of Doyle Sails took the water taxi to Foreign Affair which was moored in Port Washington. He took the necessary measurements and reviewed with us our order for our new sails. It will take 3 to 5 weeks to get the sails made. In the meanwhile, we will continue to explore Long Island Sound.

We cast off after Jamie departed and headed out to learn more about Hempstead Bay and Oyster Bay. Hempstead Bay lies between Manhasset Bay and Oyster Bay. Sand cliffs line its shores and a few grand homes sit atop the cliffs. It is less populated than Manhasset Bay with the exception of the bay's northeast corner where more modest homes have been built and several marinas provide dockage and moorings for hundreds of boats, particularly on Glen Cove Creek.

Numerous large homes lined the banks of Oyster Bay which was the home of the Long Island Roosevelts of which Teddy Roosevelt was a member. His home, Sagamore Hill is now a National Historic Site under the care of the National Park Service. Unfortunately, it was not convenient for us to visit by boat.


Re-provisioning and Back to Port Washington

Re-provisioning and Back to Port Washington


While drinking our morning coffee in the cockpit, we noticed we had a new neighbor in the mooring field. A 12 Metre race boat was two mooring balls away. She must have come into the harbor late yesterday afternoon and we didn't notice her when we returned to our boat last night after dark. There was no sign of a crew and we knew of no regattas scheduled in the immediate area. It is quite a thrill to be moored between two classic racers - a 12 Metre and a Herreshoff S Boat.

It was also exciting to learn that many of the 12 Metre yachts built in the United States were constructed right here in Mamaroneck at the Derecktor Shipyard. In fact, Carla's first time on a sailboat was on a 12 Metre, Stars and Stripes, which was built by Derecktor. We first encountered a Derecktor Shipyard in Fort Lauderdale where many yachts were being serviced. It is amazing how we are connected in some way or another with people we have met and places we have been to in the past.





Sheldrake Yacht Club Race Day

Sheldrake Yacht Club Race Day


We slept in and had a great breakfast. We cast off our mooring and went out into the bay to watch the Sheldrake Yacht Club races. We motored at the perimeter of the race course and took pictures to share with members of the club. After the races, we met with some of the club members at the Bar Harbor for drinks. Everyone was friendly and offered advice on places to go on the Sound. It was a pleasant day on the water.

Afterward, we went back to Brewer's Marina and met with Paul. Dinner was at Sal's where Dwayne ordered a wonderful veal parmesan dinner. Carla had a calzone and Paul had pizza. We went to the Italian bakery for dessert. It was another fun day.

Share this page: