Cutchogue Harbor to Three Mile Harbor

Our original plan for the day was to make a short hop from Cutchogue Harbor over to Shelter Island Sound and anchor at Southold early in the afternoon so we could go ashore and visit one or more of the many vineyards and wineries which are found on Long Island's northern fork. The area has been called the Napa Valley of New York.

As we entered Cutchogue Harbor, we encountered a large fleet of sailboats competing in a regatta. We reduced our speed and kept at a safe distance eventually joining some of the spectator boats to watch for a while. We were told it was a regatta with sailors from various high schools competing in One Design 420 sloops and another group was competing in Lasers. It was fun to watch as the wind was beginning to pick up and some of the kids were finding jibing quite challenging. Eventually, we departed to find a good spot to anchor with hopes of going ashore.

420 Regatta - Cutchogue Harbor

Our plans changed shortly after anchoring. First of all, we were advised by the harbor constable and local police that there was not a town dock and all the docks in the area were private. They knew of no place for us to leave our dinghy while we visited the wineries. Additionally, the winds were starting to increase and the forecast didn't look good considering where we were anchored. We were quite exposed from the south which was the direction from which the wind was blowing. Also, we were on a lee shore and not all that confident in the ability of the anchor to hold based on reports from others that had previously anchored there. As a result, we decided to either head to Dering Harbor to Three Mile Island to wait out the high winds forecast.

Dering Harbor was a stop recommended to us by friends. However, when we arrived it was filled with boats on moorings and the traffic in the harbor was pretty heavy. So, we decided to pass on stopping at Dering Harbor and head back to Three Mile Harbor where we knew we'd have good protection in heavy winds. Besides, we could head back into East Hampton to visit Mulford Farm and the Hook Windmill the following day.