The Pikes are in the second qualifying round for the first time in 22 years.
Tony Hackworth's men have also scooped £2,250 after shocking higher-level Redcar Athletic 5-2.
Athletic are second in NPL East, Bridlington's league, a level above Pickering.
Pikes had beaten Penrith and Easington Colliery already in the FA Cup.
Redcar led inside two minutes, but Pickering quickly turned the match on it's head as George Brown netted twice for 2-1.
Early in the second half, ex-Whitby winger Nathan Dyer crossed for Joe Wood to turn home at the back post.
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Redcar reduced the arrears from the penalty spot but Brown clinched his hat-trick with a spot-kick of his own for 4-2.
George Thewlis put the result beyond doubt with a fifth, five minutes from time.
Alfie Burnett in the Pickering goal made a string of saves to help his side to a giant-killing.
It's the only the fourth time the Pikes have reached the FA Cup second qualifying round, they have never reached the third.
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