Locally, I'll go with a few, limiting this back 30 years
1991: Hurricane Bob, "The Perfect Storm" Halloween Storm (later given Hurricane status)
1998: Late May severe weather, strong flooding summer
2005: Strong cold outbreak killed a lot of winter hardy objects, Severe October flooding, strong early December blizzard
2011: Springfield-Sturbridge EF4 tornado 6/1, Tropical Storm Irene, October Snowstorm with 25+" snow in central Mass.
2015: 75+" inches of snow in six weeks January/February
2016: Strong summer drought, combined with bad gypsy moth outbreak (which has a long tail and is more affecting stuff now five years later)
Make of any of those what you feel is the worst