This appears to be one of the more interesting routings in Massachusetts. My 1923 ALA Guide indicates that NE-17 was routed from Hudson, NY to Great Barrington, MA. It then headed south to Norfolk, CT and then out to Westerly RI via Hartford and Norwich. My 1930 ALA confirms this routing in maps; except that it went via modern US 7 & US 44 via Canaan, CT; it is unclear whether this route was used for the 1923 version. (The other possibility being that it ran through New Marlboro via modern MA 57 and CT 272; this seems fairly unlikely to me, though.)
My 1933 map shows 17 only between Hillsdale, NY and Great Barrington. (17 still extended into New York through 1928.) By 1939, the road between Great Barrington and Woronoco had been upgraded; both it and the road between Hillsdale and Great Barrington bear the number MA 23. However, a 17 also appears alongside the 23 designation near West Otis. By 1942, the 17 designation was completely missing.
17 reappeared when modern I-95 was created north of Danvers between 1953 and 1956. US 1 was routed onto the highway; what is now US 1 was given the number 17. By 1959, the highway had become I-95 and US 1 was put back onto the old routing, once again eliminating 17.