Sailing + Racing
Sagamore Sailing and Racing Program
Sailing for both the serious and the casual racer.
Since 1944 Sagamore Yacht Club has boasted a diverse and inclusive sailing program, for every degree of sailor.
Sagamore Yacht Club has an active racing program that is aimed to please both the serious and the casual racers of Oyster Bay. The Spring and Summer Wednesday Evening Series are complemented by longer weekend races of various formats as well as casual events like the Race to Dinner and annual Club Cruise.
Wednesday racing consists of two 10 week series. These evening races are within the Oyster Bay and Cold Spring Harbor area. After the races most skippers and crews gather back at SYC for libations, food service and shared stories of that evening’s race. It is here that many questions about racing techniques can be answered… sometimes even correctly.
The weekend regattas and events tend to be longer races and some are run in a pursuit format. These races will often include courses out on Long Island Sound.
The 2026 SYC racing program begins in late April and continues through mid-September.
General Information
SYC Event Calendar
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Questions, Comments, or Suggestions?
Please contact the Sailing Committee at racing@sagamoreyc.com
Announcements
- See below for the 2026 sailing event schedule!
- If you are at all interested in racing, be sure you and your crew are members of the racers@sagamoreyc.com group e-mail list and the WhatsApp group text. This will be the most timely way to get updates on events and announcements.
- Links to individual race results can always be found on the event page for that particular regatta
Racing Group E-mail List
The racers@sagamoreyc.com e-mail discussion group is used to distribute official racing related announcements, results, reminders, and for general discussion between list members of all things racing related. All skippers, crews, and those interested in racing are strongly encouraged to subscribe so as not to miss important race related updates (or tips on how to tactfully brag to the competition).
Race Committee
Interested in participating as part of the SYC race committee? Join our RC PRO Tim Hoyler onboard our race committee boat to help run the races, no prior experience is required.
Joining the RC is a great way to be a frontline spectator for both some exciting racing and for some nice harbor views and sunsets to accompany whatever libations and snacks are to be had.
Let us know by sending an e-mail to racing@sagamoreyc.com
2026 Regatta & Event Details
Once open, registration and event information, such as the Notice of Race (NOR), Sailing Instructions (SI), current entry list, and individual race results, can be accessed by following the link for each event listed below. Check back regularly as race documents are subject to change as details for each event are finalized and registration is opened. If you have any questions regarding event registration please contact Jonah Schachner, SYC Racing Coordinator, at racing@sagamoreyc.com.
To foster cross-club participation and competition, select races sponsored by our neighbors across the harbor at Seawanhaka Corinthian Yacht Club (SCYC) are included below along with links to their respective event/registration pages.
CLICK HERE to view the Regattas & Results section of the SCYC website with a full listing of SCYC events
Racing Orientation & (TBD) Rules Seminar
Meet upstairs at SYC to discuss racing for the 2026 season. This is an opportunity to get questions about registration and the NORs/SIs answered. All sailors and crew are invited and encouraged to attend.
In addition, everyone who is interested in racing should be familiar with the basic Racing Rules of Sailing (RRS). Traditionally a mini rules seminar/refresher is coupled with orientation night. and all skippers and crew are strongly encouraged to attend. The more rules knowledgeable folks on the boat, the better.
Specific details for the 2026 program will be forthcoming. .
Everyone is welcome to enjoy cocktails and/or dinner downstairs before the meeting. Please make reservations if interested in having dinner.
April 15
Wednesday Night Racing
This is our most popular racing event by far and is open to everyone. We start in either Oyster Bay Cove or the entrance to Oyster Bay every Wednesday night until late September. Our unofficial motto has been “No one gets left on the dock,” so if you are interested in crewing, please join the Racing Group E-mail List and introduce yourself to the racing community.
Registration and event information such as the Notice of Race (NOR), Sailing Instructions (SI), current entry list, and individual race results can be found on the event page for each of the two 10 week long series.
Note that the racing fee for the Wednesday Night series is for both series, there is no discount for participation in just one series. If you register for the Spring Series your registration will be automatically copied over to the Summer Series at the beginning of the event
To qualify for scoring in either series each boat must provide two crew to assist with RC duty at least once during either the Spring or Summer series. See the NOR and SI for details. Contact the RC at racing@sagamoreyc.com to sign up for an open RC slot.
Practice Race (April 29)
Warm up for the season at the practice race, no separate registration is required
Spring Series (May 6 – July 8)
Summer Series (July 15 – September 16)
Alfred Roosevelt Memorial Regatta (SCYC)
SCYC sponsored event – Link to 2026 regattas on SCYC website
May 16
2026 Execution Run
Aargh, it be a race. A race to a rock. A big rock… with a lighthouse. Come join SYC for their annual Execution Run. A medium distance day race with both spinnaker and jib & main classes. (note – cannons are not required… but they are recommended). The race is followed by a Pirate Party back at the club. All crews are invited and guest moorings will be made available.
June 6
Club Cruise
Join the flotilla or find your own way to a rendezvous with other SYC members. This year the meet-up will most likely be somewhere closer to SYC than in the prior few years. Details are TBD and will be posted when available.
Afterwards groups might sail onwards to unique and exotic locations such as Old Saybrook, Three Mile Harbor, the notorious Block Island, and points even further east afterwards. Past Commodore and SYC Fleet Captain Conny Baris spearheads this annual pilgrimage. All SYC sailors and powerboaters are invited..
3rd Week of July
Please email Conny Baris at SYC@BarisFinancial.com to express your interest in joining us
Dooley Roosevelt Regatta
The Dooley Roosevelt is a one day pursuit format race open to sailboats belonging to, or chartered to, members of the Seawanhaka Corinthian Yacht Club (SCYC), Sagamore Yacht Club, and Cold Spring Harbor Beach Club (CSHBC). The boats shall be skippered by members of their Yacht Clubs or their family.
This is a friendly race named after a renowned sportsman and olympic sailor who was a member of both SYC and SCYC. All club sailors are encouraged to participate, especially those who do not normally race as the pursuit format removes the chaos of a crowded starting line.
This race is run by SCYC and SYC on a rotating basis; SCYC is hosting in 2026.
August 1
Race Back to Dinner
A race, followed by a dinner. Not a race to eat your dinner. I mean, not a race to finish your dinner first – that would be impolite. Your mother would probably be disappointed. Just a race to get to dinner, and then eat slowly, or at least politely, while bragging about how fast you got there.
This casual race event will culminate with everyone arriving at SCYC (TBC) for cocktails and dinner in the company of their fellow participants.
August 15
Finish: SCYC (TBC)
Commodore’s Cup & Dinner
A day race, followed by a party… need we say more? This race is only open to boats owned, chartered, and/or skippered by SYC members. There is no entry fee for this race and no racing experience is needed, come join the fun!
September 12
Jack Bernstein Memorial Regatta
The final race of the 2026 SYC sailing season. If you win, you get last bragging rights all the way up until next spring!
September 26
Sailing Awards Dinner
Grab a table for your crew and come celebrate the end of another summer of sailing and racing.