Chatham Yacht Club

Teaching Love of Sailing on Pleasant Bay Since 1921 


CYC is a nonprofit organization and needs your help to run the program, keep boats maintained and keep our membership and class prices low.

As Chatham Yacht Club turns its attention to the next 100 years following its Centennial in 2021, it is imperative that we ensure the Club has the resources and foundation to thrive. We consequently are launching the Campaign for the Next Century


Chatham Yacht Club (CYC) is dedicated to teaching sailing, promoting sailboat racing, and developing a community of sailors and their families. CYC is committed to the same principles that have guided it since its founding in 1921:

  • To provide sailing instruction to children, adolescents, and adults
  • To organize and sponsor racing experiences for all ages in the Pleasant Bay area of Cape Cod, MA
  • To foster its culture based on volunteerism, inclusion, and multi-generational involvement

CYC operates as a volunteer, non-profit organization that endeavors to foster a love of sailing and the creation of relationships and memories that last lifetimes.

Follow Chatham Yacht Club on Instagram!  (latest posts below)

To see our @chathamyachtclub instagram page 

Sailing School Registration 2024

Register Now

Interested in becoming a CYC Member?

Membership Applications

Membership and Sailing School Rates 

2024 Season Rates

CYC runs on Volunteers

Volunteer here!

Latest Articles

In Memory of John Wesp

Please use the link above to donate in the memory of John Wesp Jr. 

Upcoming Events


As you know, it takes a village of volunteers to run a club like CYC

See our officers and committee members

Day Sailer Association North American Championship Regatta


July 24 – 27, 2024

Pleasant Bay, North Chatham

Sponsored by:Chatham YC (Fleet 34), Pleasant Bay Community Boating, Orleans YC (Fleet 15) and Stage Harbor Yacht Club (Fleet 18)


  • Clubhouse Opening - June 15th 0930 ALL HANDS ON DECK!
  • Sailing School begins - Monday, June 24, 2024
  • Opening Meeting - June 29th

Membership & Registration


Please see the information page and application form.

Need Help renewing your membership?

    Click here to view a membership renewal step-by-step guide.

    (Memberships are annual and must be renewed in order to register for sailing school or social events.)

    HOW TO Register for sailing school

    Once you have activated your Family With Children membership, you may register for sailing school (adult sailing classes are available to all active membership levels). Access sailing school registration from the Sailing School Menu above.

    Click here to view a sailing school registration step-by-step guide

    Membership Communications


    Wild Apricot now allows us to send email to 2 addresses associated with your account. This means that you can add your spouse's email address to the membership field called also send email communication to and both of you will receive spinsheet emails. 

    To update your profile and add information to this field, log into the CYC website, click on your username in the top right corner to bring up your profile. From there you can select edit profile to update information.

    Please note: this second email is linked to the primary account. Unsubscribe requests from either email address will unsubscribe both addresses! So, if your spouse no longer wants emails from CYC, please remove their address from the "also send email" communication to field.


    CYC Parking

    The parking lot configuration allows for multi-directional Fox Hill Road access from three points as illustrated in the diagram below. It is essential that all CYC traffic use the third entrance on Fox Hill road to minimize the access traffic and pedestrian hazards in the other parts of the parking area.

    The added parking has improved parking but we, EHCC and CYC, need to continue to optimize on the available parking with the following actions;

    Sailing School morning classes

    CYC instructors will be available to help students to and from the CYC club house so parents can enjoy the convenience of “drop and go” noted by the yellow cross-hash area. Before 11:30 am, parking may be available on a first-come, first-serve basis in the designated area, highlighted in green box, for parents to bring their children to classes, meet the instructors and fellow parents. Please be aware this area is not exclusive to CYC but shared with EHCC. If there is a shortage of parking spaces in the designated area, please park on the shoulder of Fox Hill Rd. “Pickup and go” will also be available for your convenience at the conclusion of morning classes at the Pick-up spot shown in the diagram. This is a safer and shaded location where our students can be ready for pick-up.


    Parking begins to get busy around 11:30 when Eastward Ho! Lunch service begins. After 11:30, We ask that CYC members park on the Fox Hill road shoulder during lunch if the north lot is busy.

    Afternoon classes and races

    Due to the limited amount of parking spaces, Parents are encouraged to enjoy the convenience of “drop and go” where appropriate for the children. Parents who would like to see your kids in action during the afternoon races can check for available parking spots in the designated (green) area after 2 PM. If there is a shortage of parking spaces at any time, please park on the shoulder of Fox Hill Rd.

    Eastward Ho! will have parking lot attendants available to assist with traffic flow and direct CYC members to the designated (green) area. Please don’t hesitate to speak with them if you have any questions or need assistance.

    As always, safety is paramount as we balance convenience and consideration for a shared parking resource with our friends at Eastward Ho!

    Thank you for your cooperation as we begin a new exciting season at CYC!

    Getting your boat to CYC:

    No boats or sailboards may be carried over the hill to be launched at CYC.

    Launching may take place at Jack Knife Harbor, the Town Landing on Crow's Pond, Ryder's Cove or in Round Cove. Please pay attention to any permitting needs for launching any boat.

    Transportation of 420s and Optis over the hill for the purpose of attending regattas during the summer may occur ONLY before sunrise and after sunset per our lease with Eastward Ho! (If you have purchased an Opti for your sailor and are depositing or removing your Opti for the season, these same Eastward Ho! requirements apply.

    Thank you in advance for your cooperation!

    Chatham Yacht Club | P.O. Box 531 | North Chatham, MA 02650

    CYC is a 501(c)(3) Non-Profit Organization. Your donations are tax deductible!

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