Gaps in forest habitat are well documented to negatively impact the movements of forest songbirds. Much past research on avian gap-crossing decisions has utilized playback experiments. However, playbacks are limited by short observation times and often cannot be used to reveal differences in behaviors among individuals. Here, we present a novel approach utilizing radio-frequency identification (RFID) to investigate gap-crossing decisions in Black-capped Chickadees (Poecile atricapillus). Using bird feeders outfitted with RFID readers, we were able to track the movement patterns of wintering Black-capped Chickadees within forests and across gaps. We used logistic regression and an information theoretic approach to identify the factors that best predicted gap-crossing behaviors. Gaps impeded movements of wintering Black-capped Chickadees and the best predictors of gap-crossing behaviors were gap size and gap vegetation density. Birds were more likely to make crossings with decreasing gap size and when gaps contained more matrix vegetation (1–2 m height). We recommend the primary way to increase connectivity for birds in fragmented habitats is to reduce gap distances. Additionally, it may be beneficial to increase shrubby or woody vegetation within the gap to a height of over 1 m, as this also increases the likelihood of gap-crossing.