Emily, it depends on what the weather is doing (and what I'm doing) each year. Most of the time I guess I do tomatoes around early to mid March. I found that starting them inside gave me bigger plants to babysit and plant out, but I didn't get fruit any earlier. So I just wintersow them now.
If you wintersow them, I'd recommend this tip that I got from a GardenWeb friend. Sow them in big cups, like 16 oz. size. Thin to one plant/cup. As they grow, rather than transplanting, just keep adding a little more soil to the top of the cup. Quick and easy, and the plant just keeps getting buried deeper.
Here are my tiny WSown tomatoes when planted out
Same plants in August
Karen