17 miles of Shoreline
Webster Lake is one of the largest natural lakes in the tri-state (MA, CT, RI) area. The lake is made up of three ponds connected by narrow channels. The area of the lake is 1,442 acres with about 17 miles of shoreline.
Who We Are
Sailors, Families, Friends
The Webster Sailing Association is a nonprofit private sailing club dedicated to the promotion of sailing and sailboat racing on Webster Lake. Established in 1935, we maintain a membership of about 100 members and their families.
What We Are
Wet/Dry Storage
The club is located on the center pond in a protected cove. There is dry sail parking for approximately 60 boats. Just back your boat in the water, hoist your sails and you are ready to sail. There is also a limited number of moorings available with a club dinghy available to retrieve your boat.
Our club house has a two tier deck and patio with picnic tables and gas grille. Inside there is a complete kitchen with stove, refrigerator, microwave oven and toaster oven. There are two bathrooms and an outdoor shower.
Our History
The Webster Sailing Association (WSA) traces its origins to Lake Chargoggagoggmanchauggagoggchaubunagungamaugg, where organized sailing began with the first recorded race in 1889. The association's formal roots were established in the 1930s through the Sea Scouts, led by Richard "Dick" Wales, who organized races and built essential facilities at Sea Scout Point. In 1935, regular members formed an association to assist the Scouts, marking the beginning of what would eventually become the Webster Sailing Association, officially incorporated in 1959.
A pivotal moment in the association's history came in 1960 when they purchased land at Winter Cove, establishing their permanent home. Under the leadership of Bill Boyd, who served as Commodore for 13 years, the club built their clubhouse "The Anchorage" in 1961 and continued to grow, reaching 100 members with 76 boats by 1963. The association demonstrated its commitment to sailing excellence by joining the prestigious United States Yacht Racing Union in 1953, an unusual achievement for a small freshwater club, and notably rejected a merger with the Power Boat Association in 1954 to maintain their focus on sailing.
Today, the Webster Sailing Association stands as the second oldest sailing club in Massachusetts, maintaining a rich tradition of sailing while adapting to modern times. The club has achieved not-for-profit status and maintains active involvement in lake conservation efforts, including water quality management and invasive species control. With typically full membership and a waiting list, WSA continues to honor its founding families - Benoit, Craver, LeBoeuf, and Stefaniak - while providing a welcoming environment for both competitive sailors and families seeking recreational activities on the lake, maintaining its reputation as "the best deal in town."
Read MoreMembership Information
You may join the Webster Sailing Association if you are 18 years or older and have a basic knowledge of sailing. Cost for first year is $342.00 and $265.00 for each year after. Membership fee covers all persons living in the same household and includes one boat parking space (either dry sail or mooring).
The first year of membership is probationary and each new member must demonstate their sailing skills, attend one of our two work parties and show a willingness to help with the management and maintenance of the club. We also expect all members to sail their boats on a regular basis.
New Member Application
Membership is open to qualified individuals and families. For more information
Contact the Secretary
