In reply to Ramblin dave:
I wouldnt actually book that much, just flights and a car until a few weeks before, that'll give you an idea of where conditions are good, and what you could get done. From Boston 4-5 hours either way and you have a fair amount of options.
Liftopia is good for lift tickets and need to be bought 3 days in advance, it does save you a chunk, but you can leave them til later, especially if its midweek.
If you watch web cams at different resorts and then get a decent forecast then book places later on. Skiing is expensive in the NE and the resorts close to Boston and NYC get crazy so avoid weekends if you can and go hiking on those days, but those further away such as Killington or even Sunday River can be pretty quiet midweek at that time of year. By that stage different resorts have different offers, wildcat (NH) will have a day for say $25, Mt Abram ME, near Bethel) will be $15.. something like that.. these resorts aren't huge so you can ski most of the resort at you level in a day or two.
If you are learning I'd suggest a small resort like Mt Abram midweek, We were there this year as Sunday river was getting skied out, the chair lift had broken so we just had the t-bar but that'll be working again by the start of the season, but there was loads of greens and easy blues, and it was really quiet. Maybe just get some lessons for a few hours then ski the rest of the day, then pay more for a bigger resort.
Quiet slopes are great when you are learning, much less stressful.
Hiking just depends on the year and how bad/good the winter is.