Cities have an immortal quality in the minds of their inhabitants, enduring over the span of their lifetimes, ever changing yet familiar. Prehistoric burial mounds are juxtaposed with terraces of social housing, Medieval shrines are consumed by shopping centres and subway stops, the city is a hectic jumble of deep time and the contemporary world. What can be done about this deep time of the city, and what role does it play in the lives of the shoppers, commuters, dwellers and workers who interact with the urban prehistoric landscape? The following research is an attempt to access three such sites through experimental-experiential approaches to study these Prehistoric monuments in the urban realm, to interrogate their interactions, both academically and experientially in the contemporary, near and deep pasts. This was attempted through the application of experiential field approaches to three case studies within the City of Glasgow, at Cathkin Braes Cairnfield, Camphill Earthwork and Doomster Hill. The results of the fieldwork undertaken are reported here and an account of each site has been provided detailing their academic histories from antiquarian rediscovery to the present, current interactions, and a phenomenology based interpretative narrative of their deep time pasts.