The Estonian pioneers who settled in Alberta travelled extensively, often making numerous stops and using multiple modes of transportation. At the turn of the 20th century, Red Deer saw the end of the railroad. This marked the starting point for the search for land on which to homestead. Hendrik Kingsep along with his family, was the first Estonian to settle in Alberta. The Kingsep's settled a piece of land near Sylvan Lake in 1899. His brother Kristjan and his family soon arrived and settled directly adjacent to Hendrik's home. Initially, the Kingsep's found the area around Sylvan Lake adequate as there was an abundant supply of timber and fresh water. Moreover, there were reports of Finnish people settling in the area. This made the Kingseps' settlement slightly more comforting as Estonians and Finns are closely related linguistically and culturally. Within a few years, the Kingsep's were joined by other Estonian families eager to settle in the immediate area. By 1903 there were 61 men, women and children of Estonian descent on 16 farms.
The topography of the Sylvan Lake area reminded many Estonians of their birthplace so much so that they aptly titled their settlement "Livonia." However, the area quickly became a popular settlement for other nationalities. It soon became evident that the land could no longer accommodate newly arriving Estonian families. Consequently, Hendrik Kingsep moved to the Medicine Valley, some 40 kilometres to the west in search of more open land. The Medicine Valley, with its rich, dark soil and tree-dotted landscape, again reminded many Estonians of their birthplace. Within the decade Estonian settlements were established across Alberta. For example, the Erdman's and several other settlers established the community of Barons. Within a short time, numerous other families settled nearby. Seven years later the Stettler area had become home to 45 families. Within a few years Eckville, situated in the heart of the Medicine Valley, hosted roughly 40 families. There were other sparse Estonian settlements in the northern and southeast regions of Alberta; Estonians settled in the towns of Foremost, Walsh and Peace River. Estimates of Estonians settling in Alberta by 1916 suggest that 100 families and several unmarried men moved out west. This accounted for a total population of approximately 500 Estonians.