Sailing contests in this area are recorded as far back as 1859 when Royal Navy men amused themselves with boat races by sail and by oar. One of the first regattas in the Pacific Northwest marked Victoria Day 1870 with crews from the Royal Navy Squadron in Esquimalt. Regattas were also being organized in Vancouver and Seattle which attracted yachtsmen from both sides of the border.

The Seattle and Victoria yacht clubs were formed in 1892 and that year a truly international regatta was held off Esquimalt to mark Victoria Day. This event spawned the Northwest Yachting Association which later grew into the Pacific Yachting Association in the 1920's. Interest and participation in this race and yachting generally grew over the same time.

Swiftsure Lightship mmbc collection

A plan was devised for a race to circumnavigate Vancouver Island. This perhaps overly ambitious plan was scaled down to a race starting in Victoria out and around the Swiftsure lightship and back. On Victoria Day 1930 the first 'Swiftsure Lightship Cup Race' was held. The race was an initial success but financial troubles during the depression and the subsequent war slowed its growth for some time.

The Oriole at Swiftsure mmbc collection

The first postwar race was held in 1947 starting from Port Townsend out and around the lightship and back to Victoria. The course was soon restored to the original due to adverse tidal conditions around Port Townsend. The race grew throughout the 1950s as yachting progressed and the newest designs were always present at the "Swiftsure". On July 1st, 1961 the Swiftsure lightship was replaced by modern shore stations. Since then the Royal Canadian Navy has provided a mark ship for the event each year.

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