Originally Posted by ContinentalFan
Welcome to FT!
I don't know of any airline that offers an annual pass. Southwest might be the least expensive, but you'd have to fly to Manchester and I don't think that there is a direct flight. I think your best bet is to plan your flights so that you always have a Saturday night stay.
SW does have some great prices. Manchester is only a 1 hour drive north of Boston. SW also flies from Providence which is only a 1 hour drive south of Boston. They are both nice airports to get in and out of.