Lakes region formed as sea caves during higher lake level stages and became increasingly terrestrial as lake levels receded, resulting in an abundance of rockshelters and other shoreline features that are now inland from the current shoreline. Recorded rockshelters in the region have contained human burials, copper caches, rock art, and varying amounts of lithics, ceramics, and fire-cracked rock. Additionally, a considerable amount of regional ethnohistoric accounts demonstrate the importance of rockshelters, especially those near water, as powerful transformative spaces that served as nodes between different realms of the Algonquin universe and homes to other-than-human entities, called manitous. Oral histories suggest that the power associated with these settings could be accessed through certain activities, such as fasting and producing rock art, imbuing individuals with knowledge and social capital (e.g. Copway 1850). Despite these compelling accounts, recorded examples of archaeological rockshelter use, and the relative abundance of rockshelters in the region, very few have been subjected to formal archaeological investigation.To address this disparity, archaeological testing of selected rockshelter locations on Grand Island was conducted under the direction of the Grand Island Archaeological Program in June of 2015 to assess the research potential of these features. Field work successfully identified two Woodland period rockshelter sites located on Grand Island's southern shore: Moss Cave (FS 09-10-03-1076) and Miner's Pit Cave (FS 09-10-03-1077). Rockshelter site use is examined based on analyses of artifact assemblages from these sites, including the results of lithic microwear analysis, macrobotanical analysis and AMS dating, and their respective geomorphic settings are investigated to interpret timing of rockshelter formation and availability. Using a multiscalar approach, these site-level patterns are articulated with contemporaneous habitation sites on Grand Island and similar rockshelter sites in the Upper Great Lakes to draw comparisons. Informed by a theoretical framework that seeks to accommodate the multiplicity and complexity of hunter-gatherer relationships with the landscape, and supported by ethnohistorical accounts, this research seeks to expand the interpretive potential of rockshelters in the Upper Great Lakes by arguing that they were likely considered places of ritual significance that provided a setting to communicate with manitous.