The Blues netted five at Middlesbrough's Riverside Stadium on Monday night.
Nathan Haslam's men beat Northern League First Division Boro Rangers 5-1 in the final of the North Riding Senior Cup.
Despite their opponents being from Teesside themselves, Whitby outnumbered Rangers in the stands within a crowd of 1,515.
Stephen Walker put Town ahead within three minutes and added a second around the half hour.
Rangers pulled one back soon after but Whitby's third from Alfie Doherty put the match to bed.
Nathan Thomas claimed one from Walker's shot on the line but it was definitely ex-Middlesbrough marksman Walker's goal for Whitby's fifth to clinch his hat-trick.
It's the eighth time Town have won the trophy.
Blues goalkeeper Shane Bland was delighted to end the season on a high:
Bland began his career at the Riverside and said it was a special moment to lift silverware there:
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