My PhD dissertation was on the philosophy of place, so I'm in a good place to tell you that there's really a lot out there that might be of interest.
Some of the authors that first came to mind have been mentioned already. Seconding Yi-Fu Tuan and (especially) John Brinckerhoff Jackson. Jackson's work, I think, really fits what you're looking for. His writing is wonderfully clear and diverse. I'd look into A Sense of Place, A Sense of Time, which has an entire section on 'Towns, Cars and Roads' and an essay called "Roads Belong in the Landscape". I loved everything I've read by him.
As for my own suggestions:
Edward Casey's Getting Back Into Place is, to me, the single best philosophical work on issues of place and our relation to the environment. As such it also deals with roads and paths. Also check out his The Fate of Place, a philosophical history of the concept of place.
Tim Ingold is a philosophically inclined anthropologist whose interpretation of the relation between person and place is based on the idea that we are constantly 'on the road'. He wants to re-orient our understanding of our spatial surroundings towards flows and paths, rather than boundaries and edges. I've read parts of The Perception of the Environment: Essays on Livelihood, Dwelling and Skill and Being Alive: Essays on Movement, Knowledge and Description, but just a short glance at his bibliography might pique your interest. Somewhat related to this approach: Christopher Tilley, A Phenomenology of Landscape: Places, Paths and Monuments.
Then there's (arguably) the philosopher whose thinking about place and paths has been most influential: Martin Heidegger. As a short introduction, consider his essay "Der Feldweg" yt . The best text about Heidegger's thinking of place is Heidegger's Topology by Jeff Malpas. (Casey, too.)
Finally, some authors that I haven't read myself but might be of interest: Henri Lefebvre, Michel De Certeau, David Seamon, E.V. Walter's Placeways, Rebecca Solnit's Wanderlust. Oh, and Lucy Lippard's The Lure of the Local (have read that one, also contains parts that you'll find interesting I think).
Some search terms which might help to track down even more literature: 'human geography', 'environmental aesthetics', 'architectural phenomenology' (there's a newsletter edited by David Seamon which is potentially a great resource as well.)
posted by Desertshore at 9:10 AM on September 28 [6 favorites +] [!]