There was a time when Northampton was strongly Republican. Calvin Coolidge was Mayor there for a time.
Northampton voted for Hoover in 1932 but switched to FDR in 1936 (Springfield did the same as well). It did vote for Eisenhower twice, so it wasn't all that staunchly Democratic.
Indeed. Nixon came close to carrying Northampton in 1972, while Amherst went for McGovern by a 2-1 margin (before that, the only Democrats to carry Amherst were LBJ and Humphrey). By 1984, Mondale easily carried Northampton (and received 73% of the vote in Amherst).
What's interesting is that while Massachusetts was moving in a decidedly leftward direction,
Worcester County (and the Westfield-Chicopee-Holyoke area of Hampden) was moving towards the Republicans. There's this swath of towns along the Connecticut-Rhode Island border that voted for FDR by 3-1 margins that Reagan carried (Southbridge, Dudley, Webster, Millville, Blackstone). Didn't Bush and McCain either carry this region or come close to winning it as well?
This is probably similar to what happened in New Hampshire's Merrimack Valley: what was traditionally the most Democratic part of the state now has some of the most Republican areas left in New England (Hillsborough County voted for FDR all four times, while Reagan and Bush Sr. won it by 2-1 margins).
The Merrimack and Blackstone valleys became more GOP as they became the exurbs of Boston. There's no equivalent exurban effect in the Connecticut valley.