As a member of the Yacht Racing Association and U.S. Sailing, racing has always been an important part of Sheldrake's history.

Our ambitious racing season runs from spring through fall and is designed for both the serious, advanced sailor and the novice. 

At Sheldrake, we stress fun and encourage participation, whatever the experience.

The racing season includes our historic Whaler's Race - unique for its start at anchor, with sails down. Sailors from all over the Sound compete each year for the Whaler’s Skylark Cup. 

If you are interested in entering a race, please fill out the racing form below.  Please make sure that you have filled out and returned the race waiver form.  You only have to do this once a season, not for every race.

Our 2018 racing schedule will be posted shortly. Stay tuned (no pun intended)

Our 2017 racing schedule is as follows:

Tune up race- May 20, 2017

Day race-  June 24, 2017

Day race- July 8, 2017

Day race- August 19, 2017

Day race- September 16, 2017

Whalers race- October 7, 2017


Our 2016 racing schedule is as follows:

Tune up race- May 21, 2016

Day race- June 25, 2016

Day race- July 9, 2016

Day race- July 30, 2016

Day race- August 30, 2016

Whalers race- September 18, 2016

Fall race- October 8, 2016

Unless specified, all races will begin at 1 PM from Can 1 between Mamaroneck and Larchmont with a warning signal at 12:50pm.  Racers should monitor channel #78 for instructions.


Photo Credit: Peter Hellberg

Tuneup Race

2015 Results:

1st: Katch - Len Lipton

2nd: Calypso - Rich Mintzer

3rd: Perfect Pitch - Michael Krebs

Photo Credit: Mitya Ku

Whaler's Race - Racing Division

2015 Results:

1st: Clean Sweep - Marc Berkowitz

2nd: Surface Tension - Jim Serphos


Photo Credit: dimnikolov

Whaler's Race - Cruising Division

2015 Results:

1st: Buona Vita (also engrave plaque for Skylar Cup) - Peter Luciano

2nd: Jambaby - Bruce Kalisch


Bob Pfeffer Memorial Award

2015 Winner:

Bruce Kalisch - For contributions to our club, serving on the board and publishing the newsletter for many years.

Race Entry Form

It is understood and agreed that as a condition of the participation of my yacht in any race or related activity sponsored or undertaken by The Sheldrake YC, the owner, helmsman, and each crew member whether or not to start or continue the race is solely their responsibility, and each of them waives all clains which he or any heir, successor, or assignees, may have against The Sheldrake YC of or in any way connected with participation in such race or activity,"