
Join the Fun with the Holmes Hole Sailing Association
Racing sailboats on the Vineyard Sound for 50 years.
All skill levels welcome!
The Holmes Hole Sailing Association welcomes all sailors. Any monohull boat over 15' can join in. 2026 dues are $200 for more than 20 scheduled races. Ratings are unique to HHSA and are established using past performance. Jump in and start accumulating a record.
WATCH THIS SPACE
Racing will begin around Memorial Day. Season will begin Mid June
Need more information?
Email: email@Holmeshole.org




The Holmes Hole Sailing Association Announces The 2026 Season’s Schedule
Season's Awards will include Sunday and Thursday races. Chance for a First Place Coffee Cup for any race.
Thursday evening racing will start at 5:00 PM as in 2025. VHYC Snack Bar will be open for HHSA members for Thursday gatherings. Racing will follow 2025's format. See circular and schedule.
We will allow for a Rendezvous race to Tarpaulin Cove on three favorable tide Sundays, The first of these dates (to be determined)) with good winds will be the date. More about this as the date draws near. Every Sunday race to be decided based on Conditions. Thursday races will use Course 0 or 0 Reversed, with windward starting leg in southernly winds. We will race as one class, same as 2025. See Sailing Instructions/Circular
High point scoring will again be used allowing higher scores if doing well in races with many participants. The best scores of only 60% of scored races will be used to determine season's awards. This method could allow an irregular competitor to do well. Any and all sailors are encouraged to join us at all times.
As usual, 1st, 2nd and 3rd place finishers will receive awards at season's end and the Jewett award will go to best overall performance.
Committee Boat Service no longer required! The VHYC will be providing all the necessary manpower for this. Voluntary contributions will be accepted to cover the expense.
HHSA sailors are invited to join the VHYC racers for a chance at the Jewett Bowl on Saturday, August XXX. (to be determined) Pursuit start using PHRF-NE ratings.
The Schwarz Cup will be awarded this year for best performance in minimum of 5 races in Post Season racing if attendance allows.
This year you will need to register for both HHSA and the Moffet separately, but can save $25 by registering for the Moffet by June 15th. Total of $275 for all the fun! If you are just able to sail up to 3 races, join as a Sailor for just $100. You can now pay your dues with Pay Pal or Credit Card by going to http://www.regattanetwork.com/membermgmt/HHSA/Membership_registration_start.php
Update your address, email, phone and boat information at this link also.
BONUS!
HHSA membership includes entry in VHYC Jewett Bowl Race, August XXX.
Racing begins with the annual Tune-Up race on Sunday June 15th at 2:00 PM. Thursday evening racing will commence June 19th with a 5 PM start at nun 6. With this variety of racing, every sailor should find something to enjoy!
Watch for starting line to north of Nun 6 in Southernly Winds in order to facilitate a Windward Start. Refer to 2025 Circular for all instructions.
Use the regattanetwork.com address above to pay your dues of $200 ($100 for up to 3 races) or send a check to the Treasurer, Wendell Colson, 115 Main Street, Vineyard Haven, MA 02568. (508 878 9061) New members please submit an entry form so we can “fit” a handicap. Any monohull boat within reach is welcome for the entire season or just a race or two. Ratings are updated after several races based on performance relative to the group. Come as a guest one time to try it out...email your intentions the day before: rgbecker@Yahoo.com
Winners are often decided by seconds after racing for an hour and a half!
The ISAF Racing Rules of Sailing apply but remember this is Handicap racing for fun and we hope people self-administer the rules and do the two circles when necessary. Keep in mind the differences in the maneuverability of the various classes of boats and note the Life Jacket requirement for all racers.
Results are posted on the Blog (See button above) and emailed to the Holmesholesailors google group as soon as available.
After the Thursday evening races, all HHSA sailors are invited to enjoy a dinner at the VHYC snack bar where results will be announced.
Please help each other improve their sailing skills by joining in the after race discussion of tactics, strategies and the Racing Rules of Sailing.
Cups are awarded for first place for each race and seasons awards are awarded at the annual meeting and pot luck dinner to be announced.
Moffett Race (9/6/2025)
Requires a separate entry. ($100) Register by June 15th and save $25
EXTRA!
Sail Martha’s Vineyard Vineyard Cup Racing weekend has been scheduled for Saturday and Sunday (July 12 and 13 for 2025, 2026 dates to be determined). PHRF-NE Rating certificate required.
Holmes Holers are encouraged to participate in the Edgartown Yacht Club’s “Round the Island Race” PHRF-NE Rating certificate required. Go to www.rtirace.org and www.phrfne.org for entry information. July 25, 2026
HHSA LINKS HELPFUL LINKS

Join the Holmes Hole Sailing Experience
For 50 years, we’ve raced sailboats in Vineyard Sound. Join us to have fun sailing at any level with any boat you own. Adventure awaits on the water!
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Sailing
Join us for fun racing on the water.
Contact info
email@holmeshole.org
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Race your boat all summer long or just one time: Sunday Afternoons and Thursday Evenings.