Our Staff
Mary Trester
Executive Director
Mary joined AWA in October 2022 as the Executive Director. Mary has a passion for learning, community and boating which makes her work with the AWA a great match.
Mary brings over two years experience in leadership training as the Program Manager of Leadership Skagit. She also has decades of experience in higher education, workforce development, equity and diversity training, and program management as the Director of Continuing Education at Edmonds College. Mary obtained her B.A. from the University of Washington before obtaining her K-8 teaching certificate from Central Washington University. She earned a Master’s in International Management from the Thunderbird School of Global Management.
Mary loves the water and in her free time you will find her boating in the San Juan and Gulf Islands with her husband, Chuck, and Chocolate Labrador Retriever, Finley. She also loves crabbing and zipping around in her Boston Whaler in pursuit of the catch of the day. Mary is a member of the Anacortes Yacht Club and serves on the Board of Directors for the Anacortes Chamber of Commerce.
Shawn P. O’Connor
Waterfront Program Manager
Shawn O'Connor learned to sail when he was 11, and has been racing and coaching ever since! Shawn started his racing career at Race Week on a Peterson 37, racing that boat through middle and high school. A founding member of the Oak Harbor High School sailing team in 2014, Shawn taught sailing camps since 2013 with Oak Harbor Youth Sailing. He was announced as the head coach of Wildcat Sailing in August of 2020, leading his alma mater to program best finishes at NWISA Fleet Race Championships twice (2021 and 2022, 6th at both) and NWISA Singlehanded Champs (4th in 2021, 3rd in 2022 and 2023). In 2024 as the coach for the Anacortes High School Team, Shawn led the Seahawks to three program best finishes, 7th in the ranking season, 6th at NWISA Fleet Race Championships, and 4th at NWISA Team Race Champs.
Shawn is a NWISA board member and is dedicated to expanding competitive youth sailing access to communities in the Pacific Northwest, with a special focus on North Sound communities. Shawn is also an extremely active keelboat racer, winning back to back North Sound Championships aboard the San Juan 24 'Juan Solo' in 2022 and 2023, San Juan 24 North Americans in 2022, Round Whidbey in 2021-23, Whidbey Summer Classic in 2021-2024, PITCH in 2023 and 2024, and the Puget Sound Sailing Championships in 2024 among others. Shawn is a substitute teacher in Oak Harbor and is excited to help lead a competitive team in Anacortes!
Chloe Cook
Middle School Sailing Race Team Coach
Chloe grew up in Port Townsend and has always loved the ocean. She learned to sail when she was 9 and started racing with the high school team at 11. She also enjoyed sailing in the Youth Racing Circuit regattas over the summer, first in Optis, and then Lasers. She has competed at nationals in high school for Port Townsend, and in college for Western Washington University.
Chloe also loves sharing her sailing knowledge and has years of experience coaching and teaching sailing. She coached a Laser racing team for high schoolers in Port Townsend and was an instructor for college PE sailing classes for years. She also led the Western Washington University summer youth Learn to Sail program and adult lessons. She has spent many hours coaching teammates one on one, running drills at practices, and giving chalk talks. Some of her happiest memories are of being out on the water with her teammates in this beautiful place we live!
When she is not on the water, Chloe enjoys hiking, backpacking, and camping with her husband, gardening, and cooking yummy food.
Hannah Ellis
Middle School Sailing Green Team Coach
Hannah Ellis was born in Anacortes and currently lives in Oak Harbor, where she learned to sail and eventually raced varsity on the high school sailing team. She is an instructor for Oak Harbor’s learn-to-sail summer camps as well as a coach for their middle school sailing team. She is passionate about youth sailing and loves coaching and instructing whenever she can! She also enjoys keelboat sailing and races on her family’s 25-foot boat for many local regattas. Hannah is US Sailing Level 3 certified, has experience coaching both adult and youth sailors, and is excited to be a part of getting more kids into a sport she loves!