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OAKCLIFF SAILING INCORPORATED
OYSTER BAY, NY · EIN 272002488 · Form 990 · FY2025 · NTEE N40 · Recreation & Sports · Medium ($1M-$10M) · oakcliffsailing.org
revenue
$3.0M
expenses
$3.5M
net assets
$4.0M
employees
19
volunteers
110
program ratio
86%
profile · synthesized from sources

OAKCLIFF SAILING INCORPORATED is a nonprofit sailing training center based in Oyster Bay, NY, focused on developing competitive sailors for offshore, match, and fleet racing. It operates as a workforce training center for professional careers in sailing and the marine industry, offering programs for youth and adults of all skill levels. The organization runs premier regattas, supports Olympic hopefuls, and provides hands-on training through offshore races and high-performance boat clinics.

irs program accomplishments · form 990 part iii · fy2025

What they reported doing

  1. #1 primary $795K
    OFFSHORE COMPETITION: BUILDING ON LAST YEAR WHEN THE VINEYARD RACE WAS FULLY BOOKED, OAKCLIFF SENT 6 BOATS AND 92 SAILORS TO BERMUDA AND BACK IN THE LEGENDARY NEWPORT TO BERMUDA RACE. THE KER 50 WAS 3RD IN CLASS AND OC86 WITH 24 YOUNG SAILORS ON BOARD WON MANY PRIZES INCLUDING THE HAWKINS YOUTH PRIZE. ADDITIONALLY, 27 OAKCLIFF SAILORS UNDER 24 COMPLETED THEIR VERY FIRST BERMUDA RACE. OAKCLIFF ALSO RACED BOTH MACKINAC RACES ON THE GREAT LAKES. TEMPTATION THE JV66 ROUNDED OUT THE SEASON BY COMPETITING ADMIRABLY AT THE ORC WORLD CHAMPIONSHIPS IN OCTOBER.
  2. #2 $1.18M
    INTERNATIONAL TRAINING & EVENTS: OAKCLIFF HOSTED 14 GRADED MATCH RACE EVENTS AND THE TRIPLE CROWN SERIES. THE TRIPLE CROWN IS TO SUPPORT OLYMPIC HOPEFULS AND PROVIDE DIRECT ATHLETE SUPPORT THAT US SAILING OAKCLIFF ADDED THE ILCA 6 AND ILCA 7 FLEETS. OAKCLIFF SAILORS BROUGHT HOME THE BRONZE MEDAL FROM THE OLYMPICS. THIS MEANS THAT OAKCIFF HAS SURPASSED ANY OTHER PLACE, INCLUDING THE NGB IN TRAINING OPPORTUNITES AND SUPPORT OF OLYMPIC ATHLETES. ADDITIONALLY OAKCLIFF CONTINUES TO RUN MORE MATCH RACING THAN ANYONE ELSE IN THE WORLD AND AS A RESULT AMERICAN SAILORS HAVE RISEN TO THE TOP OF THE INTERNATIONAL MATCH RACING RANKINGS.
named programs · 5 · from sources

What they call their work

Acorn and Sapling Training Programs
Comprehensive residential programs for individuals 15+ to develop professional sailing careers; includes physical training, boat work, and personalized coaching across all disciplines.
Custom High Performance Training & Charters
Offers tailored coaching and charter opportunities in high-performance boats like Nacra 17s and 49ers for teams preparing for regattas or Olympic Development Programs.
Match Racing Program
Operates as the most active match racing center in the world, hosting graded events like the Oakcliff International and Triple Crown Series using twelve Match 40s; develops boat handling, rules knowledge, and teamwork.
Offshore Racing Program
Trains sailors for long-distance races including the Newport to Bermuda Race, Marblehead to Halifax, and Ida Lewis Distance Race using large boats like OC86 and Farr 40s; emphasizes seamanship, navigation, and leadership.
Supporter Sailing
Engages donors and community members in weekly fleet racing, coached sessions, and social events aboard Shields, Lasers, and Match 40s; serves as both outreach and fundraising.
activities · 7 groups

What they do

  • Recreational Boating and Sailing Programs 3 activities
    • Offshore and long-distance racing campaigns with trainee crews
      Conducts offshore racing campaigns in events including the Newport to Bermuda Race, Mackinac Races, Vineyard Race, Annapolis to Newport Race, and Ida Lewis Race, providing hands-on training in seamanship, navigation, and leadership aboard boats such as OC86 and Farr 40s.
    • Sailing training programs for novice to Olympic-level sailors
      Offers structured sailing training programs including two-week summer intensives, 3- to 6-month apprenticeships, and custom coaching for individuals and teams across multiple disciplines. Programs are open to participants aged 15 and older, serving sailors from beginner to Olympic levels through the Acorn and Sapling programs.
    • Winter and seasonal sailing training programs
      Offers the Winter Sapling program and seasonal fleet racing opportunities, including training in boat maintenance, professional coaching, and racing in Swedish Match 40s, Shields, and turbocharged Farr 40s through local and regional racing series.
  • Leadership Development Programs 1 activity
    • Corporate team-building and custom sailing programs
      Provides customizable corporate programs including leadership seminars, communication sessions, and sailing outings for groups of 5 to 75 participants, combining professional development with on-water activities.
  • Higher Education Career Placement 1 activity
    • Graduate job placement and professional sailing career development
      Prepares trainees for professional roles in sailing, with over 90% of graduates employed in high-level positions including America’s Cup campaigns, Olympic preparation, and offshore racing, and many achieving international success.
  • Amateur Sports Competition Programming 1 activity
    • Hosting competitive regattas and match racing events
      Organizes and hosts regattas including the Oakcliff Triple Crown series, Oakcliff International match racing competition, and graded events such as Clinegattas and Halloween regattas to support Olympic hopefuls and develop sailor proficiency.
  • Student Housing and Residential Services 1 activity
    • On-site housing and residential support for trainees
      Provides on-site dormitory housing at the Oakcliff Bunkhouse for trainees in the Acorn and Sapling programs, with single-gender bunk rooms accommodating up to eight athletes and shared living facilities.
  • Financial Aid and Scholarship Access Programs 1 activity
    • Tuition assistance and financial aid for trainees
      Provides scholarship programs and annual financial aid awards to support trainees in the Acorn and Sapling programs, enabling broader access to sailing training and apprenticeships.
  • Uncategorized 4 activities
    • Advanced coaching and skill development clinics
      Delivers seminars, clinics, and clinegattas led by elite coaches, along with private advanced-skill instruction and match racing drills, to develop sailor proficiency across multiple boat classes and competitive formats.
    • Charter and race sponsorship programs for external teams
      Offers bare boat charters and race sponsorship deals that integrate Oakcliff trainees into external racing campaigns for events such as Around Block Island, Melges 24, and Farr 40 regattas, as well as providing access to high-performance boats like Nacra 17s and 49ers.
    • Historic boat campaign and competitive representation
      Prepares and campaigns historic vessels such as the 12 Metre Courageous at international championships, using crews composed of trainees from the Acorn and Sapling programs to gain high-level racing experience.
    • Prize and participation grant awards for competitive sailors
      Provides financial awards to competitive sailors, including $24,327 in prize grants for ILCA 6 and ILCA 7 competitors in the Oakcliff Triple Crown and $10,000 for teams at the Oakcliff International, as well as participation grants for 49er teams.
financials · form 990 · fy2025
revenue
Total revenue$2.96M
Contributions & grants$2.38M80%
Program service revenue$165K6%
Investment income$-8K-0%
Other revenue$424K
expenses
Total expenses$3.50M
Program expenses86%
Admin / overhead9%
Fundraising5%
Salaries & benefits$710K
Grants paid out$0
Largest expense lineFacilities
balance sheet
Total assets$4.78M
Cash$574K
Investments$0
Liabilities$771K
Net assets$4.01M
Liquid reserves2.0 mo
6 years on record · 2020–2025 · YoY revenue -5.5%
leadership · form 990 part vii · fy2025

Who runs it

paid leadership · 1
NameTitleHours/wkCompensation
DAWN RILEY EXECUTIVE DIRECTOR 60 $243K
board members · 7
  • ART SANTRY — VICE PRESIDENT
  • DENISE BENOU STIRES — BOARD MEMBER
  • DOUG REYNOLDS — BOARD MEMBER
  • KIRK RADKE — PRESIDENT
  • MATT KELLEY — BOARD MEMBER
  • NIGEL CLARK — TREASURER
  • WILLARD FREEMAN — BOARD MEMBER
relationships · 18

Who they work with

  • Acorn Programs Partner — Collaborates on scholarship opportunities for Sapling apprentices.
  • Alumni Partner — Contribute to scholarship funding through individual donations.
  • America True Partner — Awarded scholarships to Oakcliff Sailing trainees, continuing a shared mission of youth sailing development.
  • Bitter End Yacht Club Partner — Sponsored an all-girls high school team that participated in the Newport to Bermuda Race under the Oakcliff program.
  • Chris and Duncan Williford Partner — Olympic hopeful 49er team receiving special grants for participation in Oakcliff regattas
  • Gary Jobson Partner — Provided experience and insight to the Oakcliff team during the 2023 Courageous campaign.
  • Ian Barrows and Steven Hardee Partner — Olympic hopeful 49er team receiving special grants for participation in Oakcliff regattas
  • Kimbra Walter Partner — Owner of the 12 Metre Courageous who supports Oakcliff’s campaign with the boat.
  • Long Beach Yacht Club Partner — Represented by Dave Hood, who presented an invitation to the Congressional Cup at the Oakcliff International.
  • Mark Walter Partner — Co-owner of the 12 Metre Courageous who supports Oakcliff’s campaign with the boat.
  • NYYC Partner — Collaborates on events such as the NYYC Annual Regatta, referenced through shared imagery and programming context.
  • Parents Partner — Provide financial support for scholarships through individual donations.
  • Riptide Racing Partner — Hosted team Riptide Racing, led by Chris Poole, in the Oakcliff International regatta.
  • Ryan Wood and Ed Colman Partner — Olympic hopeful 49er team receiving special grants for participation in Oakcliff regattas
  • Sagamore Yacht Club Partner — Co-hosts Wednesday night fleet racing events with Oakcliff Sailing.
  • Stirling Harbor Foundation Partner — Joins Oakcliff Sailing in classic yacht racing events with shared participation in Friday Shields racing.
  • The Sailing Museum Partner — Collaborates with Oakcliff and the Walters to showcase diversity and opportunity in sailing to museum visitors and the community.
  • True Blue Racing Partner — Hosted team True Blue Racing, led by Gavin Brady, in the Oakcliff International regatta.
strategies · 3

How they approach the work

Named approaches extracted from this org’s sources. Where others share an approach, follow it to see the full set of orgs running it.

  • Career Pathway Development Through Integrated Industry Networks
    methodology: career_pathway_networking
    By integrating workforce training with professional networking and real-world crewing opportunities, OAKCLIFF enables career transitions into the marine industry, because direct access to regattas, race campaigns, and industry connections bridges the gap between training and employment.
  • Equitable Access via Merit-and-Need-Based Selection
    methodology: merit_and_need_based_access
    By selecting trainees based on drive, leadership potential, and financial need rather than prior experience or background, OAKCLIFF promotes diversity and equitable access to professional sailing pathways, because this approach identifies high-potential individuals who are otherwise excluded from elite maritime training.
  • Experiential Professional Training Through Racing
    methodology: experiential_professional_training
    By using offshore and competitive racing as a training platform, OAKCLIFF SAILING produces skilled maritime professionals, because immersive, real-world experience in seamanship, navigation, and leadership builds competencies more effectively than classroom-based or simulated instruction alone.