California has, in recent years, become a hotspot of interannual climatic variability, recording devastating climate-related disturbances with severe effects on tree resources. Understanding the patterns of tree cover change associated with these events is vital for developing strategies to sustain critical habitats of endemic and threatened vegetation communities. We assessed patterns of tree cover change, especially the effects of the 2012–2016 drought within the distribution range of blue oak (Quercus douglasii), an endemic tree species to California with a narrow geographic extent. We utilized multiple, annual land-cover and land-surface change products from the U.S. Geological Survey (USGS) Land Change Monitoring, Assessment and Projection (LCMAP) project along with climate and wildfire datasets to monitor changes in tree cover state and condition and examine their relationships with interannual climate variability between 1985 and 2016. Here, we refer to a change in tree cover class without a land-cover change to another class as “conditional change.” The unusual drought of 2012–2016, accompanied by anomalously high temperatures and vapor pressure deficit, was associated with exceptional spikes in the amount of both fire and non-fire induced tree cover loss and tree cover conditional change, especially in 2015 and 2016. Approximately 1,266 km² of tree cover loss and 617 km² of tree cover conditional change were recorded during that drought. Tree cover loss through medium to high severity fires was especially large in exceptionally dry and hot years. Our study demonstrates the usefulness of the LCMAP products for monitoring the effects of climatic extremes and disturbance events on both thematic and conditional land-cover change over a multi-decadal period. Our results signify that blue oak woodlands may be vulnerable to extreme climate events and changing wildfire regimes. Here, we present early evidence that frequent droughts associated with climate warming may continue to affect tree cover in this region, while drought interaction with wildfires and the resulting feedbacks may have substantial influence as well. Consequently, efforts to conserve the blue oak woodlands, and potentially other vegetation communities in the Western United States, may benefit from consideration of climate risks as well as the potential for climate-fire and vegetation feedbacks.