i'm running 42x16 on my langster's SS side (69 gear inches with 700x23 tires), which seems to be the perfect gearing for the just-west-of-Boston roads. i can hammer up nearly every single hill i encounter and i can easily hit 20-22mph on the flats before spinning out. anything faster and i usually pedal like crazy for a short period and then just coast.

edit: my point is that a jump to 44 may be too much right away. try 42 and you should be happier with your ride.