Cross Sound Challenge

A new race in 2018, the Cross-Sound Challenge, features a destination finish in Oak Bluffs on Saturday, August 29 and a return race to Hyannis, called the Tiny Cup Race on Sunday, August 30.  This will be the 3rd qualifying race in the 2020 HYC Wilbur Cup Summer Series.

A significant weather event, Hurricane Laura has derailed our plans yet again, and the race is now scheduled for September 5th. Most likely we will not race to Oak Bluffs; because of the Coronavirus, it will not be safe to go ashore and so a race finishing off Hyannis is preferred. the Tiny Cup race is canceled.

The Cross-Sound Challenge start will be early morning off the Hyannis Breakwater and then we will race to the entrance of Oak Bluff's Harbor on Martha's Vineyard. The return race, now known as the Tiny Cup Challenge, will be from Oak Bluffs to Hyannis the next morning. The return race will require the use of each boat's racing handicap (Spinnaker) to encourage cruising boats to use their spinnakers. Trophies will be awarded for both races.

Oak Bluff's Harbor allows rafting on their moorings.  We are hoping to raft 3-4 boats together per mooring, so that we can share some camaraderie. There is no reservation system but we are assured that there will be no problems at that time of year.  Dockage does require reservations through Dockwa.  Skipper's who want dockage should reserve a slip, as soon as possible.

Last year we were able to include PHRF racers from around the bay - power or sail - racing or non-racing – we met in Oak Bluffs for a casual social gathering. It was a great success, and we hope to repeat this year. Depending on the size of our party, we plan on meeting for cocktails and dinner at a local restaurant. Dinner and drinks are on an individual basis.<

Please sign up early, so we can reserve the moorings and set up the meeting place to have dinner.

For more information about the race contact HYC Ocean Class Chair, Roy Catignani at or Vice-Chair Marc Fater at


2020 Cross Sound Challenge Results