Plan of road heading uphill and back (5)
I believe the answer is:
draft
'plan' is the definition.
(drafting is a kind of planning)
'road heading uphill and back' is the wordplay.
'road heading uphill' becomes 'dr' (I am not sure about this - if you are sure you should give a lot more credence to this answer).
'and' is a charade indicator (letters next to each other).
'back' becomes 'aft' (associated in meaning).
'dr'+'aft'='DRAFT'
'of' acts as a link.
Can you help me to learn more?
(Other definitions for draft that I've seen before include "form of conscription" , "plan outlined" , "conscript" , "Draw an outline" , "Outline or sketch" .)