The subalpine ecotone is experiencing significant changes in habitat availability and connectivity as a result of climate change. The conversion of meadow habitats to forests has been observed in many mountainous regions. Rates of conifer encroachment into meadows appears to have increased in the 20th century, but the patterns of conifer establishment seem highly variable over both space and time. To understand how and why these changes vary temporally and spatially in the Pacific Northwest, we collected cross-sections and whorl counts from conifers along four transects in subalpine meadows around Mt. Baker, Washington. We quantified the relationships between temporal patterns of conifer establishment and a suite of climate variables, and between spatial patterns of conifer density and microsite characteristics. Our results show that establishment occurred in pulses throughout the 20th century, with greater establishment on drier sites during periods of greater precipitation, and greater establishment on wetter sites during periods of higher temperatures. We found that April precipitation and September temperature are particularly strongly correlated with establishment rates, suggesting that the best conditions for conifer seedling establishment occur in years with the warmth and soil moisture needed for the growing season to start earlier or last longer. Within individual meadows, conifer seedling establishment was greater on convex surfaces and in areas with a higher percentage of Vaccinium cover. Our findings at Mt. Baker show that periods of conifer establishment occurred somewhat synchronously across multiple mountains in the region, but we also identified distinct spatial and temporal differences linked to local site conditions.