Annual Deer Harbor Wooden Boat Rendezvous
The Rendezvous is held each year Tuesday - Thursday of the first week of September in Deer Harbor. There are rowing and sailing races, pot lucks music and a BBQ for owners of and those interested in wooden boats form the region and San Juan Islands. It is sponsored by the Wooden Boat Society of the San Juan Islands, The Boat Works and the Deer Harbor Business Association.

International Schooner Race
The annual schooner race starts from Deer Harbor on a Sunday mid-July and continues on a six day series of races into Canada. It is sponsored by The Northwest Schooner Association, the Schooner Martha Foundation, Deer Harbor Marina with the help of the Wooden Boat Society of the San Juan Islands.

Boundary Cup: 6 meter Regatta
6 Meters sailboats from Canada and the US meet at Four Winds Camp on West Sound the second weekend of September to sail a series of races for the Boundary Cup. The fleet for the three day event is a mixture of traditional and modern wooden 6 Meters. It is sponsored by the Puget Sound 6 Meter Fleet, Four Winds Camp, The BoatWorks and the Wooden Boat Society of the San Juan Islands.