Wachusett Mountain

One of my faovirte place for early morning turns on the weekend or during the week before work.  Not much challenging terrain but you can get your legs going before the crowds invade the place.  If there's a powder day, go someplace else, they groom everything religiously here to maintain their base.  In short, get here early and ski a half day (you get $5 off if you return your ticket before 12:30.) 

The review of Wachusett Mountain  www.wachusett.com  by Mattias99 is pretty fair - I would add a thing or two to the info he posted.
I am also a P/T instructor there - Wawa sells a huge program of 8 weeks of night skiing to MANY elementary and middle schools in MA., so they NEED a large pen of instructors to show for lineup! It's 6 weeks of instruction, 2 weeks of free skiing. Kids are a huge part of the skiing population at Wawa, so night/weekday skiing is pretty crowded because of this. 
Also,  the folks at Wachusett have developed a very very good ITC program. It's open to any age group, and prepares the attendees for a possible P/T gig teaching for them, and perhaps to go further w/ the sport (PSIA, etc.) The staff that teaches the teachers is very dedicated and talented - many Level II and III skiers there to mentor and coach you.
It is a wonderful place to get your legs under you, for new skiers who needa good start w/ an instructor, and also for the pro wanna-be, as the instructor training is so good it is actually a model for other programs elsewhere.
Have fun this winter wherever you ski!  

(Disclosure: I teach in the ski school at Wachusett.)

Wachusett Mountain is the closest ski resort to Boston that could reasonably not be referred to as a "bump".  With 1000' of vertical and a summit at ~2000', it's the highest point in Eastern/Central Massachusetts and offers some decent skiing with reasonable amenities and a few nice perks.

While fairly small compared to the bigger resorts up in NH/VT/ME, it's less than 90 minutes each way from downtown Boston, and less if you live in the suburbs west of the city (or in Worcester, where it's about 20-25 minutes).  You can make an easy half-day trip there from Boston -- not something you're probably going to do even to, say, Loon or Waterville Valley.  Wachusett also offers night skiing on almost all their trails (open until 10PM every night), which is great for getting some runs in after work, or doing an afternoon/evening trip on a weekend day.

Obviously, Wachusett does not offer the same kind of terrain that a bigger resort can serve up.  The trail selection is fairly limited, with only two black diamond-rated trails (they don't even *try* to pretend that they have something that needs to be called a double-black.)  However, the selection of beginner and intermediate terrain is pretty good.  There is essentially no off-piste skiing of any kind; they are in the middle of a national forest, so it's illegal to go out of bounds -- and the very dense trees would stop you quickly in most spots even if you tried.  (Patrol may occasionally overlook a few people hiking up to the very top of the summit, which is a couple hundred feet above the top chairlift, after a big dump.  But you didn't hear that from me.)  There is a fairly active NASTAR community, if you are into local racing.

On the plus side, they have extremely good snowmaking -- even if it's been warm in the surrounding areas for a few days, they can usually keep almost everything open and have good cover.

There is also a fairly large terrain park.  They took out the superpipe last year, citing the expense of building it and the fact that it tended to ice up really badly in the only spot they could fit it.  (That area was filled in with more rails and a large jump last season; I haven't seen what they have planned for this year.)

There is a large base lodge, with food (both self-serve cafeteria style and a sit-down restaurant), places to stash gear (including pay lockers), and a full service shop.  The soups and sandwiches are pretty good and the prices aren't completely absurd.  You can also rent out a suite, which is a little pricey but could make a good 'home base' for a large group and would prevent having to jockey for table space downstairs.  (I think you can also get catered food if you get a suite, but I've never looked into it.)

The on-mountain shop has a fairly good selection of gear and skis/boards/boots, but they can't really do bootfitting (extensive adjustments, footbeds, etc.)  The repair/tuning guys seem to do a good job and generally have a quick turnaround time.  Demos are available; you can try up to three boards or pairs of skis for one demo fee (which is also deducted from your purchase price if you buy within a certain number of days).  They host a large ski/board swap in October.

Wachusett also has a large ski and snowboard school, with (IMO) an above-average number of experienced instructors for the size of the resort.  It helps that they can support a large population of part-time instructors who have day jobs in Boston and Worcester, many of whom have been teaching there for years and have L2 or L3 certifications from PSIA/AASI.

Overcrowding on weekends and holidays -- especially after any sizable snowfall -- can be pretty bad.  While they have two high-speed quads, lines can still get quite long in the late morning and early afternoon.  Supposedly "expert" skiers/riders bombing down crowded runs can be a serious issue, especially when far less experienced skiers/riders are in their path.  They also run programs with many local schools -- which means that the lower slopes will be overrun with inexperienced kids on weekday afternoons, and certain trails will be closed from time to time for high school races.  And the lodge, while fairly large, can get extremely crowded around meal times.  However, they are rarely crowded early in the morning or for the night skiing sessions, even on otherwise busy weekends.

There is also pretty much zero nightlife (other than the night skiing).  I mean, they have a bar, but that's about it.  That said, you could just drive down to Worcester (or Boston!)

And like any resort not way up in the mountains, they're at the mercy of the weather to produce good snow cover.  No matter how many snow gun towers and fans they have -- if it's too warm, they can't make snow.  The elevation helps, but the weather can still be fickle, especially in the spring.

Lift tickets are not hideously expensive -- the best deal is the "3-Peat" card, which gets you three visits (on any day, doesn't have to be consecutive) for $100.  The cheapest "Bronze" season passes (all day on weekdays except school holidays, and all weekend nights) are also extremely popular with locals, and are dirt cheap if you buy them early in the season.

I wouldn't recommend driving hours and hours to get there -- go a little further and hit a bigger resort.  But if you live in Sourthern New England and you need some turns on a Sunday afternoon, or you're looking for some lessons to get back in shape or improve your technique, Wachusett is the place to go.