Year-Round Staff

Paul Sheridan

Executive Director

Paul has made a career of working with children in the outdoors. He leads Four Winds * Westward Ho with an eye towards carrying on its tradition of creating a supportive and challenging environment for children and a place focused on simplicity, community, and creativity.

Paul discovered summer camp as an adult, while working for a traditional camp in Wisconsin as a wilderness trip leader during the summer after his graduation from Columbia University. One summer turned into many after Paul discovered the magic of children’s self-discovery in a supportive and beautiful outdoor setting.

In between that experience and coming to Four Winds * Westward Ho, Paul earned a Master’s Degree in Environmental Education from the University of Minnesota Duluth, and worked for a wilderness therapy program in Northern Idaho.

Paul came to Four Winds in the winter of 2004 as Camp’s Assistant Director. The Four Winds community and its commitment to children impressed him. Five years later Camp’s Board of Trustees asked him to step in as the Director. Paul believes that leadership is about service, and he takes the responsibility of caretaking the traditions of Four Winds seriously. Affectionately known as “Redbeard” during the summer, Paul considers himself a Four Winds lifer. Paul and his wife Linda live year-round in Ruth Brown’s home, Hilltop, with their kids and dog. They feel privileged to call Four Winds Camp home.

Paul is actively involved on the local and national level with the American Camp Association, the Camp Owners and Directors Association, and the Western Association of Independent Camps. He is currently the President of the Western Association of Independent Camps. He also serves locally as the treasurer of the Orcas Island Education Foundation, and as a trustee and chair of the Investment Committee for the Orcas Island Community Foundation.

Diana Huff

Associate Director

Diana Huff discovered her passion for youth development and transformative power of summer camp in 2010 at an American Camp Association (ACA) conference. After graduating from the University of San Diego, she worked as the Summer & After School Director at a private school in Orange County before becoming the Summer Camp Director at AstroCamp, a mountain science camp, in 2018. There, she saw firsthand the impact of the overnight camp experience in fostering social skills and personal growth for both campers and staff.

Diana is actively involved in the camp community, serving as an ACA accreditation visitor, instructor, and Professional Development Chair for the ACA Local Council of Leaders. She has also held the role of Education Chair for the Western Association of Independent Camps (WAIC).

Now thrilled to join the Four Winds community as Associate Director, Diana looks forward to contributing to its rich legacy. When not in camp mode, she enjoys traveling the world and spending time with her niece and nephew in Bend, Oregon.

Daisy Sessions

Assistant Director

Daisy has been coming to camp since 2007. As a former camper, counselor, and Head of Four Winds, she has spent many summers on Orcas and loves to create the camp experience for others. Daisy graduated from the University of British Columbia in 2022 with a major in history and a minor in Latin American studies. When she is not in Canada or at camp, you can find Daisy in the East Bay, California, surfing or making jewelry.

Scott Cann

Carlyn Captain

Captain Scott has held a USCG license since 2000.  In the summer of 2024, he returned to Four Winds * Westward Ho after nearly a 10-year hiatus. He lives in Seattle with his wife Kristen and their two children, LeRoi and Gracie.  He also has a heavily used library card and enjoys spending time with his dog, Kima.  He is adept in designing and installing marine electronics.  He looks forward to every summer because he gets to inspire a love and respect for the Salish Sea and maritime culture in the campers that sail aboard Carlyn.

Alli Cobb

Groundskeeper/Gardener

Since graduating from the University of Puget Sound in 2014, Alli has worked a variety of jobs in outdoor education, expedition experiences and youth development in her two home spaces, the Bay Area in California, and the Salish Sea in Washington. A renaissance woman with many interests and experiences, she found her way back to Orcas island in January 2022. Leaning heavily on her experiences in gardening and shadowing her general contractor father she is quickly learning the tools of the trade in the maintenance department assisting in all of the exciting projects happening here on the property. With a love for art and a creative flair, she appreciates and is looking forward to keeping the tradition of artful, functional facilities alive. She can’t wait to meet the campers and involve them in new projects around camp!

Eli Falen

Maintenance Assistant

Eli hails from Moscow, Idaho, where he worked in construction before finding Four Winds. The chance to work in such a unique natural setting fits perfectly with his personality. He has spent much of his life outdoors camping, hiking, and canoeing. He attended Prince William Sound College in Alaska, where he continued to improve his outdoor recreation skills by learning how to introduce others to outdoor fun safely. Eli has extensive outdoor certifications, including Emergency Response Training, Leave No Trace (LNT) Certified, Adult and Child First Aid and CPR, Wilderness First Responder, and American Canoe Association Sea Kayaking levels 1 & 2.

Joe Goldsmith

Boatwright

Daphne Opperman

Family Experience Manager

Daphne grew up in San Francisco and began her Four Winds experience at the age of 9. She was a camper, CT, AC, Counselor and Head of the Garden during her years at camp. Daphne attended Scripps College in Claremont, California, and spent a wonderful year abroad in Florence, Italy. Before joining the Four Winds year-round team, Daphne was an Executive Assistant for the Vice President of KNTV Sales in San Francisco, the Admissions Director at Mount Tamalpais School in Mill Valley, California, and most recently an Insurance Underwriter for a California based Insurance Company. Daphne and her husband Matt live in Erie, Colorado, and have three boys, two of whom are current campers. Daphne is with her boys on Orcas during the summer months and works remotely from Colorado during the school year.

Linda Sheridan

Special Projects Manager

Linda Sheridan has been a familiar face around Camp since 2005 when she moved here with her husband Paul. She joined the year round staff, as Camp’s Special Projects Manager, in 2013 and she loves being involved with the camp community. Prior to joining the year round staff, Linda worked at Moran State Park as the Interpretive Specialist, Orcas Rec as the Director, and Children’s House Preschool as a teacher. When Linda is not working she is usually hanging out with Paul, their daughters Emma and Elizabeth, and the family dog Piper. If she is really lucky she is out snowboarding, hiking, riding a horse, or traveling with her family.

Caleb Weichert

Head of Maintenance

Caleb grew up in the small town of Waterford, California where he lived for almost 30 years. After graduating from college he got the travel bug and went backpacking through Europe and explored several US states and National parks until he finally found his way out to Orcas Island and Four Winds Camp in May of 2016. He served as Camp’s Maintenance Assistant until June of 2020, when he stepped to lead the Maintenance Department. During his free time Caleb enjoys hiking, sightseeing the islands, practicing photography, and serving as volunteer firefighter and EMT with the Orcas Fire Department.