Oregon's most famous sailing ship was the Western Shore, the only clipper ever built in the state. Captain Asa Meade Simpson and his brother, Captain Robert W. Simpson, designed the ship and had a 50 percent ownership interest in it. In 1874, master shipbuilder John Kruse built the clipper at the Simpson shipyard in North Bend on Coos Bay at a cost of $80,000.

The Western Shore—also known as the Oregon Clipper—was launched October 10, 1874. It was 184 feet on keel (204 feet overall in length) and 133 feet high, with a beam of 43 feet. The ship had a capacity of 1,188 tons. The three-masted, square-rigged vessel was built of Douglas-fir and Port Orford cedar, and the cabins were paneled in myrtlewood, laurel, and mahogany. The ship was unconventionally square in the rig, having the yards on the fore and the main masts nearly the same height.

Clipper ships are sharp-prowed, tall-masted craft; like all clippers, the Western Shore was rigged for speed. The Western Shore set speed records to England: Portland to Liverpool in 101 days in 1876; San Francisco to Liverpool in 103 days in 1877; and Columbia River to Liverpool in 97 days in 1877. In spite of these achievements, the Western Shore was built in an era when steamships were increasingly taking freight from sailing ships, and no other clippers were built in Oregon.

On July 9, 1878, as the ship neared San Francisco carrying coal from Seattle, the drunken captain, H.W. Hotchkiss, mistook the bobbing lights of another schooner for the lighthouse signal. The ship hit Duxbury Reef, ripping out the ship's bottom. As the Western Shore sank, the captain and crew made the lifeboats to safety. Only the masts—sails set—remained above water. An aggrieved Asa Simpson called it "vandalism."