Yes it is possible via different methods. You could even draw road on that surface using Grease Pencil tool - Bsurfaces addon; Shrinkwrap modifier; Snap modes are some to use.
There’s no measurement tool like e.g. ruler in G Sketchup. It is possible to set show Edge lengths in N-panel; then in edit mode insert/add temporarily edge between points you need to measure. Edge lenght will be shown for selected.
What a timesaver!
I use the array- and curve-modifier to generate the street out of a single meshsegment. The result can then be projected onto a surface, thats great.