In late summer or early fall, the eastern fairy–slipper produces a single leaf that remains green over winter. The next spring, shortly after melting snow exposes this leaf, a frost tolerant bud emerges. One of the earliest orchids in Manitoba, it has been observed in bloom along the Bird River in the eastern portion of the Province as early as the 3rd week of May. Normally the first week of June is the best time to search for this diminutive beauty. In Manitoba the most prolific colonies of Calypso bulbosa are found growing over the limestone base of the Interlake region with large colonies occurring in the Grand Rapids area. A gently sloping habitat seems to be preferred, where moisture can slowly migrate over a limestone strata beneath the organic layer of duff. This orchid can also occasionally be found in cedar bogs of south eastern Manitoba and in cool beds of moss along the streams and rivers of the northern Canadian Shield. In July 2004, a report of the occurrence of this species at Churchill was confirmed.

The name of this orchid is taken from the sea nymph Calypso in Homer’s Odyssey. In Greek Calypso means “hiding” or “concealment”. Because of its preference for pristine wilderness areas and its early blooming habit, few individuals other than dedicated orchid enthusiasts or naturalists ever get to see this orchid. First discoveries of this orchid always elicit exclamations of wonder. To be fully appreciated the blossom should be viewed from its own level. The very specific habitat requirements ensures failure should the plant be moved, thus it is best appreciated where found.