I usually sow my tomatoes in March. I take clues from the weather, and this is an exceptionally warm year. I just did them a couple of days ago.
There's no reason why you couldn't sow them in winter. But if you get an early stretch of warm weather and they sprout, they'll freeze out when cold weather returns. So I'd just rather wait until it's safer. I sowed them a few days ago. If frost occurs after they sprout, I'll give them some protection.
Kassia, I think if you wintersow short DTM tomatoes, they should do fine for you. (but I've never gardened in Ma) Longer DTMs might not bear much fruit before frost. Even here, I usually do some short and some longer DTMs to give us tomatoes over a longer time.
But with wintersowing, remember- you're always at Mother Nature's mercy. Last year was my worst tomato year ever, but nothing in my yard, even the flowers, did well last year. It was my lowest tomato production in 25 years of growing them. Most people here related the same, even from store bought plants. Blame the weather.
For you, unless you've gotten lights, you might want to wintersow them, at least your short DTMs.
Karen
