In the 1830s, Inuit in Cumberland Sound, Baffin Island, lived a traditional lifestyle as yet untouched by the incursions of Scottish and English whalers. During that decade, the whaling industry suffered a series of devastating disasters, and many whaling captains argued that new strategies were required to allow the business to thrive again. William Penny, a Scottish whaling master with considerable Arctic experience, felt that Cumberland Sound, explored by John Davis in 1585 and 1587 but not reentered since by European explorers, might prove to be the lucrative whaling ground that would revitalize the industry. The task was to find its entrance.

In 1839, after fishing in Baffin Bay, Penny put in at Durban Island, off the east coast of Baffin Island, to question Inuit there about Tinujjiarvik, a large inlet on the coast to the south, which some Inuit had already reported to whalers. There he met a young Inuk, Eenoolooapik, with whom he was to collaborate.

Eenoolooapik had been born at Qimmiqsut, an island off the southwestern coast of Cumberland Sound, about 1820. When he was a boy, stories reached his camp about the whalers who frequented the Davis Strait coast. Eenoolooapik's father relocated his family to Durban Island in the hope that he would be able to acquire trade goods from the whalers. The voyage was long and dangerous, made by native umiak, a traditional traveling boat made from bearded sealskin stretched over a driftwood frame. The family followed the coast of Cumberland Sound to Cape Mercy, then north along the Davis Strait coast past Cape Dyer. On the voyage, Eenoolooapik observed the coastline carefully.

Eenoolooapik drew a chart of Cumberland Sound for Penny. The whaler was so impressed with the young man's knowledge that he invited him to accompany him to Aberdeen to spend the winter. He hoped, with Eenoolooapik's assistance, to gain publicity and government support for an exploratory voyage to find the entrance to the sound. With the consent of his family, Eenoolooapik accompanied Penny aboard the Neptune in October 1839 and reached Aberdeen on November 8. The earliest surviving version of Eenoolooapik's chart, untitled, bears the erroneous legend, "Sketch of the Inlet discovered by Captn. W. Penny in 1839." (Penny did not enter Cumberland Sound that year.) It is an obvious amalgam of Eenoolooapik's and Penny's knowledge, and a tribute to the well-known map-making ability of Inuit. The depiction of Cumberland Sound, with all place names in Inuktitut, was solely the product of Eenoolooapik, and shows less detail than the Davis Strait coast. North of Cape Enderby, the detail is more certain, the work of Penny using existing charts, and all but one of the place names are in English. The map shows in detail the route taken some years earlier by Eenoolooapik and his family from Qimmiqsut to Durban Harbor, opposite Durban Island. A subsequent version of the map, without Eenoolooapik's family's route, was subsequently published on February 12, 1840, as Admiralty Chart 1255, bearing the title "Cumberland Isle" and the legend "From the Observations of Captain Penny of the Greenland Ship Neptune of Aberdeen, and from the Information of Enoolooapeek [sic] an Intelligent Esquimaux." This was the only Admiralty Chart ever published with attribution in part to an Inuk.

Eenoolooapik's arrival in Scotland created a sensation. Known as Eenoo, Bobbie, Robbie, or Robbie Durban, soon after his arrival he gave a demonstration of his kayaking prowess, in full Inuit dress, on the River Dee. His winter in Scotland was marred by ill health and he was often confined to bed with lung infections. Yet he mastered the English alphabet and some very simple reading and writing.

In early 1840, Penny learned that the government had declined to offer any financial assistance for an exploratory voyage to search for Cumberland Sound. The Lords of the Treasury approved the meager sum of twenty pounds to provide Eenoolooapik with goods to take home. Supplementing this with donations from his friends, he chose "fowling-pieces with powder and shot, edge-tools of various kinds, culinary utensils, and clothing in abundance."

Eenoolooapik left Aberdeen on April 1, 1840 with Penny, who was in command of the Bon Accord. The ship proceeded first northward along the Greenland coast to Melville Bay for whales, before attempting to reach Cumberland Sound. Eenoolooapik met many Inuit on the Greenland coast and expressed surprise that they were able to converse with little difficulty. On July 27, off the coast of Baffin Island, they reached the mouth of a large inlet unfamiliar to Penny, who was convinced that this must be the long-sought Tinujjiarvik. Eenoolooapik confirmed that it was. But Penny concluded, on the basis of existing maps, that the inlet could not be Cumberland Sound. Thinking it was a new discovery, he named it Hogarth's Sound. (The following year, other whalers renamed it Northumberland Inlet, but within a few years it was renamed Cumberland Inlet.) Ice prevented an immediate entry, but on August 2, in company with two other ships, the Bon Accord entered the inlet. It reached Qimmiqsut, where

Eenoolooapik had an emotional reunion with relatives. He remained with the ship, however, guiding Penny to the head of the sound, before returning to Qimmiqsut, where he quickly married and headed inland to hunt caribou.

Ironically Penny took no whales in 1840. The voyage, an exploratory success, was a financial disaster. In 1844, Penny returned to Cumberland Sound, where Eenoolooapik, now father to a son, joined him aboard ship and assisted in the whale fishery; Penny took seven whales. The following year he took 19 whales and in 1846 four, each year working with Eenoolooapik's assistance. Eenoolooapik's trip to Scotland had afforded him considerable status among his fellow Inuit, and he traded with his people and amassed quantities of whalebone to trade with the whalers. In 1847, Penny did not reach Cumberland Sound until September, when he learned of Eenoolooapik's death.

Eenoolooapik was but one member of a family of accomplished travelers. A sister, Kurking, migrated to Igloolik, and another sister, Tookoolito or Hannah, visited England in 1853 and later served as interpreter and guide to Charles Francis Hall. After 1840, Cumberland Sound was the most lucrative whaling ground of the eastern Canadian Arctic.

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