This chapter presents a supplementary view to post-medieval European migratory traditions by exploring the architectural forms, spatial organization, and material culture of winter houses and discusses how this is leading toward a new understanding of the periphery in rural Newfoundland communities. As early as the 1660s, cutting wood and sawing boards was considered an important part of the winter activities. At the same time wealthier members of early Newfoundland society hired men to go hunting and furring over long distances. The earliest archaeological evidence for winter housing comes from the Sunnyside 1 site, in Trinity Bay, Newfoundland which has been investigated by Barry Gaulton and Steve Mills since 2010. The other thoroughly investigated winter house sites are located in St. Mary's Bay, Newfoundland behind the small community of O'Donnells which Anatolijs Venovcevs investigated in the summer of 2015. They all date from approximately the 1820s to 1840s and hug the southern shore of a tidal pool called Big Mussel Pond.