The painting depicts the 1906 Auckland Anniversary Regatta for the Trading Vessels (vessels over 20 tons) Race. The round bilge scow Vesper leads the scows Seagull, Gannet and Reliance followed by the black hulled scow Kahu and white hulled schooner Zior. The cliffs of the North shore can be seen to the right of the painting with Rangitoto lighthouse in the background. The ketch rigged Vesper and the other scows are racing with every possible sail hoisted; water sails, ringtails, topsails and jackyard topsails. Some of the vessels have salmon-coloured sails. Painting the canvas sails was believed to prolong their life.

The vessels started off the Huddart Parker flagship Zealandia anchored near Queens Wharf at 9am. The course took them around Tiritiri Matangi from which they returned in a very fresh south-westerly wind. Vesper led the race from north of Rangitoto Lighthouse round Tiri and back to the finish. Vesper finished first on handicap, followed by Seagull and Kahu.