Look around park on initially chilly evening (5)
I believe the answer is:
recce
'look around' is the definition.
'park on initially chilly evening' is the wordplay.
'park' becomes 'rec' (I've seen this in other clues**).
'on' is a charade indicator (letters next to each other).
'initially' suggests taking the first letters.
The initial letters of 'chilly evening' is 'ce'.
'rec'+'ce'='RECCE'
(Other definitions for recce that I've seen before include "Mil. survey" , "Scout" , "Scouting expedition (colloq.)" , "Shufti" , "Military survey" .)