I grew up in MA so I know your area well. In your state I like to heat from May first through as much of October as possible unless you have
too much of a falling leaf situation. Some of my heartier  customers start in April if they are having good weather. You need to have a heat
pump that will run when it is below 50F to make this happen. The nights and some of the days in spring and fall can still be a little nippy. I
have some heat pumps that will keep heating down to the lower 30’s. Ask me about them. If it is colder than the 30’s and you want to swim
outside then you are a polar bear and have my full respect, but I will need to get you a gas heater and a raw seal.