There is a LOT to consider here. I hesitate to get into a discussion as to "best", as we'll get everybody and his/her brother/sister simply advocating for their kids' program, often to try to confirm that it is a good one.
First, it sounds like you are planning to day trip/drive both weekend days so that your kids can do this. Is the right? Second, the choices and "plan" could vary quite a bit based on where you plan to live in the Boston Area. South Shore, Metro West, North Shore......the drive times and the best "direction" to head to vary quite a bit.
Most of the bigger programs in New England, if we consider ME, NH, and VT to start, are very weekend, every vacation day programs, starting as early as they have reasonable snow, and running through in most cases the end of March or first weekend in April. And, the majority of the kids are living either full time those mountain town areas, or more likely are in a vacation/ski home. I'm saying that because a those ages, kids can be cruel without intending to do so. "Who are those kids who drive up here every weekend? What don't theie parents have a ski house here? etc."
Then you have the question of your U14. In the "best" programs, the best U14's are already going to be in full time residential ski academy programs, or living at home, in the ski home with a parent. In the more Northern and bigger programs, the numbers of weekend racers evaporate as you become a U16. Some work hard to support a program, but it's hard to not make them second class citizens to the academy kids.
My wife and I have been at this since we were young kids. 60 years ago. And we raised a couple of ski racers, who raced through college and now in there in their mid 30's coach full time in VERY big intense programs.....in the Rockies.
I would consider programs that have enough scale so that they have plenty of kids, and which also can and do attract good coaches. Now.....this is a very personal bias borne out of observation of so many programs, coaches, and kids. Kids who I have seen grow in many directions in the sport. I would want a program where at there ages the focus is on developing their ski skills.....not having somebody just drill holes and put plastic in the hill to "run gates." My son will out three or four skiers in the USST this season, and even at their ages, the amount of directed free skiing that that do is considerable. I do NOT se that in most weekend programs in N.E., unless at the biggest "hills."
So drive wise, you're NOT going to be headed to Sugarloaf, or Sunday River, or probably Franconia Ski Club. Waterville Valley would be a push {every day}. I think that heading to the Mount Washington Valley {North Conway area} could be really a slug with traffic. In Vermont, a lot of my suggestions, like MMSC or GMVS....Okemo and Killington seem exhausting for day driving.
There are some very good smaller programs that take the academy stuff off the table. You likely will have parents who do not think they have the next Mikaela sleeping in the bedroom next to theirs. I'd probably Google maps them from where you think you may be.
In Maine, Shawnee Peak is a option. I think it would be at the far end of your drive range. But it's got a good program, all weekend kids. In New Hampshire, Pats Peak is a good possibility. Clearly look at Waterville Valley. Many weekend kids. Vermont is tough, and it depends on your drive time. Stratton and SMS is always an option, but maybe for this non weekend resident drive program I might not head there.
In Massachusetts you have, actually some VERY good options. Depending on how small a mountain you ended top with, I'd been in a weekend a month of road tripping to a big mountain for a ripping weekend of free skiing. You mentioned Wachusett. I have a good friend who's kids learned to ski and race there, and stayed their through high school. Both were NCAA college captains. You can get a TON of ski training volume at Wachusett and you can probably ski with them a night a week, maybe two if so moved.
In the Berkshires, I'd check into Berkshire East and Catamount as strong possibilities, along with Jiminy Peak. With COVID a lot of these smaller areas have had a bunch of challenges recently, but I think that they will be ready for great seasons coming up.
I know that we have people in this community who ski all of them on a regular basis, and who may have some insight. The GM at Catamount, I believe, is Mark Smith who took the job to help develop the type of racing that I think you may be looking for. Mark is one of the best and most experienced coaches in the country. Former Head Coach at Middlebury, he moved back East having been the Head women's coach at Ski Club Vail. He knows how to build, staff, and run a program for ages 6-18.
My hands-on experience is with Burke, CVA @Sugarloaf, Gould/GSR at Sunday River, Holderness School {prep school}, and SMS. A bit with Waterville. But none of those program fit, IMO.
Of course if you were to plan or consider a season rental of a condo, many more options.
So.......let's narrow it down and get more to weigh in. Driving by the day? 2.5 hours one way with the kids sounds like a LONG day to me. Two days in a row over a weekend? Wow. My kids were exhausted at the end of the day at those ages, and our commute to our ski house was by skis. We had to pry them out of the car on Sunday nights. And we had a series of Suburbans so each kid had their own seat, space and dog.
You're taking up to 2.5 hours each way, up and back, two days a weekend, right? Or am I mis reading that!
Best.
