æt ðɪs tˈaɪm, ˌɛnwˈaɪ tˈuːhˈʌndɹɪd fˈoːɹɾi ˈeɪt wʌz ɐsˈaɪnd tə ðə pˈoːɹʃən ʌv ɪts mˈɑːdɚn ɹˈaʊɾɪŋ nˈɔːɹθ ʌv ɡɹˈiːnwʊd wˌaɪl ðə sˈɛkʃən bᵻtwˌiːn ˌɛnwˈaɪ nˈaɪntiːn ænd ˌɛnwˈaɪ fˈoːɹhˈʌndɹɪd sˈɛvəntˌiːn ðˈɛn ˌɛnwˈaɪ sˈɛvəntˌiːn wʌz dˈɛzɪɡnˌeɪɾᵻd æz nˈuː jˈɔːɹk stˈeɪt ɹˈaʊt sˈɛvəntˌiːn dʒˈiː. ˌɛnwˈaɪ tˈuːhˈʌndɹɪd fˈoːɹɾi ˈeɪt wʌz ɛkstˈɛndᵻd saʊθwˈɛstwɚd ˌoʊvɚɹ ˌɛnwˈaɪ sˈɛvəntˌiːn dʒˈiː ɪnðɪ ˈɜːli nˈaɪntiːnhˈʌndɹɪd fˈoːɹɾi z.
At this time, NY 248 was assigned to the portion of its modern routing north of Greenwood while the section between NY 19 and NY 417 (then NY 17) was designated as New York State Route 17G. NY 248 was extended southwestward over NY 17G in the early 1940s.