If you can afford it, Lenox has great schools, a central location -10 min to pike, 15 to Great Barrington, 5 to Lee, and 10-15 to Pittsfield.

I don't think you'll find too many really bad areas in the Berkshires.

Your biggest issue will be proximity to schools.

Dalton or Lee are anong the best somewhat reasonably priced options in the county. South county is becoming a bit more expensive lately, Lee is starting to fall into that trend as well. Great Barrington has already become expensive.

Oh, Williamstown is pretty nice, too. Nothing like having one of the best colleges on the planet in a picturesque small town. But it's in the NW corner and far from everything. But the college has tons of cultural opportunities.

I'd take a few weekends and travel the area. So much to love out here...

This is a highly unlikely scenario. But Rutland Vt was/is known as a major trafficking point.

We worry more about bears in season than anything else...

"In the name of god...."

Red Lion Inn Stockbridge. Great restaurants in Barrington, Stockbridge, Lee and Lenox. Great for casual walks and hikes of all types.

There are some world renowned spas in the Berkshires as well you could check out. These could easily push a grand/night. But after spending 2 days there you'll think it's a bargain...

What's your idea of a great city?

Greylock should be great next weekend. If you want to head the Western mass, there is also Tyringham cobble, it's always a great uncrowded hike, and Monument mountain in Barrington.

Both are pretty easy, but may not have quite the spectacular views of peaks in VT or NH though.

It depends on what kind of life style you want to have. I probably wouldn't pack up and go until I had a stable job for a while, even though jobs are fairly plentiful, Because you don't want to be stuck working somewhere you hate just to make your rent payment....

I'd do the same thing that any financial adviser recommends, an absolute minimum of 3 months, ideally 6 months of living expenses.. In this case I would include your anticipated rent in whatever location you're planning on moving to. 6 months of expenses living free at your parents house is a lot different than 6 months expenses in an apartment.....

We actually split our time between 3 states, CT, Berkshire county in Massachusetts, and MN.. Winters are rough but most people there don't seem to mind. I love it there, so much to do year round. Great food, culture, and people. The North country is gorgeous, up toward Duluth. But no dispensaries, at least for now...

Our son went to a very highly regarded small LAC about 45 minutes South of the cities. My wife and I fell in love with the area and decided it would be a great place to spend time. If you're from the cities, we're near one of the places where it's not too hard to get a great view of the city once a year..edit : the one by us is not open once a year.

We lived a number of years in the South. No thank you..

"Set my compass north, I've got winter in my blood.."

Glad you enjoyed it. If you do enjoy the outdoors it's a great 4 season place to live or visit. It's a bit of an undiscovered gem, and we like it that way...

If nothing else, bring it camera and take some of the back roads in the area. If you like to drive there are options for beautiful ways to get up to Pittsfield besides taking the Pike all the way to rt7.

Do a quick search of Berkshire county and something will come up that you can do or visit...

No, I just think we take it for granted. I have a relative who's lived in San Diego during their entire lifetime, they've never been to the beach. Sometimes you don't always appreciate what you have in your own backyard...

Yeah, but I'd rather be in Cambridge than pretty much almost anywhere in the Midwest, except for Chicago or MSP (One of our houses is there anyway, it's a great city, We spend a couple months a year there). I've been out that way enough to know...

There are some interesting inclusions and exclusions on the list.

I don't think people appreciate the quality of life we have up here in the northeast, even if it is a little bit colder than other parts of the country, and a little more expensive. And it does appear the northeast was very heavily represented in the list...

Only get up that way about once a year now.. Some of the most beautiful unspoiled and uncrowded land you will find anywhere in the country. And some great driving roads in the area as well.

Spend a lot more time in SoCo Berkshire County now.

Beautiful area. Some nice restaurants in town on both sides of the bridge.

Miss not being able to walk down and sit in the glacial potholes.Used to do that growing up...

Had a friend who owned a condo the road leading into that ( until last year) said it's patrolled regularly and even if you were to walk your dog out that way on the road you're likely to get approached.

If you're looking for something that hasn't been through the auction system ( These tend to be cars the larger dealers don't want for some reason), skip all the dealerships on rt5 between Enfield and east hartford.

But it would be helpful to know more specifically what you are looking for. And maybe a price range too...