2026 Regattas

We are proud to announce that Oakcliff Regattas for 2025 and 2026 have reached Sailors for the Sea Gold level for clean regattas. 

click here to request an invitation to any 2026 oakcliff match racing events                

CLICK HERE APPLY FOR THE OAKCLIFF MATCH RACE ACADEMY IN PARTNERSHIP WITH THE WMRT 

2026 Match Racing Schedule:

• David Storrs Grade 3 Clinegatta and Qualifier for the USMRC: April 17-19 (clinic 4/11)
• May Grade 5: May 2-3
• June Grade 3: Qualifier for the Thompson Cup & Chicago Grand Slam – June 5-7
• June Grade 5: June 13-14
• US Youth Match Racing Championship for the Rose Cup: June 25-28
• July Grade  4: with the WMRT Academy– July 17-18
• July Grade 3: with the WMRT Academy – July 24-26
• August Grade 5: August 8-9 
• Oakcliff International Grade 2, part of the Grand Slam: August 27-30
• September Grade 5: Sept 26-27
• October Grade 5: Oct 10-11
• HALLOWEEN Grade 3 Invitational: Oct 30-Nov 1

ALL MATCH RACING Overview Link  

 

 

• Around Block Island Race: May 22-24, 2026
• Newport to Bermuda Race: June 19-22 
• Shorthanded Return Race: June 28-July 1
• Bayview Mac Race: July 18-19
• Alpena Delivery: July 21-24
• Vineyard Race: Sept 4-6
• Refit My Ride: Oct 12-24 

   

Visit our offshore programs for more details on training.

 

 

 

Oakcliff Prize Grant Documents

Prize Grants Terms and Conditions  and Notice of race  Coming early 2025

Expense Report Form

Eligibility Form

TRIPLE CROWN 

• Stage 1: June 15-18, 2026 -West Sayville NY
• Stage 2: August 14-16, 2026 – San Pedro CA 
• Stage 3: September 12-13, 2026 – Oyster Bay NY
• Stage 4: September 19 -20, 2026 – Oyster Bay NY