Meteorological and hydrologic conditions associated with shallow landslide initiation in the coastal bluffs of the Atlantic Highlands, New Jersey remain undocumented despite a history of damaging slope movement extending back to at least 1903. This study applies an empirical approach to quantify the rainfall conditions leading to shallow landsliding based on analysis of overlapping historical precipitation data and records of landslide occurrence, and uses continuous monitoring to quantify antecedent soil moisture and hydrologic response to rainfall events at two failure-prone hillslopes. Analysis of historical rainfall data reveals that both extended duration and cumulative rainfall amounts are critical characteristics of many landslide-inducing storms, and is consistent with current monitoring results that show notable increases in shallow soil moisture and pore-water pressure in continuous rainfall periods. Monitoring results show that shallow groundwater levels and soil moisture increase from annual lows in late summer-early fall to annual highs in late winter-early spring, and historical data indicate that shallow landslides occur most commonly from tropical cyclones in late summer through fall and nor’easters in spring. Based on this seasonality, we derived two provisional rainfall thresholds using a limited dataset of documented landslides and rainfall conditions for each season and storm type. A lower threshold for landslide initiation in spring corresponds with high antecedent moisture conditions, and higher rainfall amounts are required to induce shallow landslides during the drier soil moisture conditions in late summer-early fall.