The 13-year-old was presented on Thursday with the Sir Peter Blake Leadership Award for being an outstanding leader in Queenstown Primary School.
The house captain said he felt ''really humbled'' to be presented with the medal and a prize pack, including a biography of the late decorated yachtsman and a pair of his trademark ''lucky red socks'', in a special surprise assembly of year 7 and 8 pupils.
Westpac bank manager Fiona McLister presented the accolade to applause.
''It's pretty awesome to get an award,'' Chester said after the presentation.
''It's pretty inspiring, too, especially from Sir Peter Blake.''
The member of the Wakatipu Kindergarten leadership programme, the literary quiz team, Central Otago hockey team and QPS News, among a wide range of school activities, was nominated and voted by his peers and teachers.
Fellow pupil Kayde Hollebon said he had ''all the characteristics of a great leader.''
Teacher Lynda Thomas said she could ''always rely on Chester to do the right thing.
''He makes good choices with a smile and is keen to share and help.''
Chester heads to Wakatipu High School next year and said he wanted to pursue ''a career in the sea like Peter Blake''.
