ðə sˈɛɡmənt ʌv mˈɑːdɚn ˌɛnwˈaɪ θɹˈiːhˈʌndɹɪd fˈaɪv nˈɔːɹθ ʌv kjˈuːbə wʌz ɚɹˈɪdʒɪnəli ðə sˈʌðɚnmˌoʊst pˈoːɹʃən ʌv ɹˈaʊt sˈɪkstiːn, ɐn ʌnsˈaɪnd lˈɛdʒɪslətˌɪv ɹˈaʊt ɐsˈaɪnd baɪ ðə nˈuː jˈɔːɹk stˈeɪt lˈɛdʒɪslətʃɚɹ ɪn nˈaɪntiːnhˈʌndɹɪd ˈeɪt.
The segment of modern NY 305 north of Cuba was originally the southernmost portion of Route 16, an unsigned legislative route assigned by the New York State Legislature in 1908.