Before 1600, Europeans overwintered in northern North America only rarely and usually by accident, as in the case of Basque whalers trapped by ice at Red Bay in the 1570s. There is one record, in an early Cornish account book, of what sounds like an over-wintering caretaker in Conception Bay in 1609 (a year before John Guy's colony at Cupids). It is sometimes claimed that English fishing ships regularly left winter crews behind at this time, but there is no other evidence for this. In fact, the suggestion seems unlikely.

Red Bay Harbour, Labrador. Basque whalers in Red Bay preferred to construct their shore stations in locations which were both close to deep water and sheltered from the northeast and southwest winds. These stations were most frequently used during the whalers' seasonal visits to the harbour. In the 16th century, the Basques (like other European visitors) did not usually overwinter in Labrador, but returned to their home ports in the Bay of Biscay until the next whaling season. Adapted with permission by Duleepa Wijayawardhana, 1998. Adapted and reproduced by permission of J.A. Tuck, Atlantic Archaeology Ltd. From James A. Tuck and Robert Grenier, Red Bay, Labrador: World Whaling Capital A.D. 1550-1600 (St. John's, Newfoundland: Atlantic Archaeology Ltd., ©1989) 38.

From the time of Elizabeth I a series of writers advocated the settlement of Newfoundland. Four are distinguished by their extensive first-hand knowledge of the island: Anthony Parkhurst (1578), Edward Hayes (1586), John Mason (1620) and Richard Whitbourne (1620). The schemes of the 1570s and 80s came to nothing. Humphrey Gilbert's visit to St. John's in 1583 is sometimes misunderstood as an effort at Newfoundland colonization, but it was not. Gilbert had plans to exploit "Norumbega", that is, the coast of Maine. St. John's was just a port where he found it convenient to supplement his lean provisions by bullying the European fishermen he found there. After their visit to Newfoundland both Gilbert and his companion Hayes became more interested in the possibilities of northern settlement, but Gilbert was to drown a few weeks later on the way to his proposed southern colony. And Hayes, like Mason and Whitbourne after him, lacked the capital to finance a colony and could do little more than publicize the possibilities they saw.

The early proponents of Newfoundland settlement offered various grandiose reasons for their schemes, but the special advantages of the island were more relevant and these were, largely, related to the fishery. Whitbourne, for example, in his Discourse and Discovery of Newfoundland (1620), defended colonization of the island with most of the rationales usual at the time, from "converting the Inhabitants to Christianitie" to disburdening England of its "superabounding multitudes". But he presented in greatest detail the case that settlement would permit a more efficient fishery. He also suggested that overwintering crews would be able to pre-empt fishing rooms. This raised the possibility of establishing a monopoly on the dry fishery, and it is possible this was a disguised part of the strategy of the Newfoundland Company, which backed John Guy's colony at Cupids. Whatever the calculations behind these early plantations, those that were successful in establishing permanent residents were fishery-oriented.

In 1621 John Guy told the House of Commons that there were "But three real plantations in Newfoundland". He was probably thinking of Bristol's Hope (Harbour Grace), St. John's and the newly-founded Colony of Avalon at Ferryland.

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