Best towns in Berkshires? (Pittsfield, Hudson: for sale, houses, theatre)

[ScreechHawk]

Hi everyone,

My wife and I are looking to relocate to a nice town or village in Western Mass (or the NY Taconics/mid-Hudson area). Must haves: small town feel, good neighbors, access to outdoors (hikes, canoeing, etc), arts and creative folks, farmers markets/organic food, and, last but not least, housing that we can actually afford.

We've heard good things about Great Barrington, Lenox, and Pittsfield. Can you confirm this (or not), and/or add to this list? Thanks for your help!

[tao777]

Hey Screechhawk, where are you coming from? Any chance you can visit the area for a few days, get a feel?

I grew up in the area and then lived there recently -I'm an artist.

It's a great area -the communities can be a little tight-knit/closed-minded, Lenox, where I grew up has changed a bit in that there are more 'outsiders' that the businesses are catering to (if not sucking up to) there are still the long-time locals there thru thick and thin that may be a bit wary.
But the schools are great (we went to Private), and certainly the area is beautiful. Be sure you're OK with real wintery conditions...
Great Barrington has become more chic and cosmopolitan...almost though a 'wannabe' feel, but that's certainly a good family community...they may be a little wary of outsiders.
What I found recently are GREAT little towns- relatively 'undiscovered' outside of Great Barrington...I can not for the life of me think of the names -Egremont, S. Egremont. If you're looking for smalltown/farmtown, rural, quaint, that's what I saw, and the prices are still reasonable. I saw old farmhouses -gorgeous, so quaint- for sale.
Heading out towards the NY border like you said, also good towns, and not a bad commute (rt 7 I believe). Toward the Conn. border as well...I wondered why I hadn't heard more about these towns...less expensive living and easy access to the 'action' -Great Barrington.
Stay away from Pittsfield, I'd say. Keep heading North if you're looking that way. Stockbridge is pricey but wonderful -you've got theatre, the arts, the Stockbridge Bowl...oh there's a town adjacent...can't remember the name -THAT's the 'up-and-coming' residential area! I just forget the name at present. Shoot...
If you have more questions, maybe I can help! Just email...

[ontheroad]

Good info from the OP.

Also if you check rte 22 (NYS) up to the Berkshires you'll find some great towns/villages.

I lived in Sherman CT (summers only) and went up to Tanglewood and other events easily in an evening.

Beautiful countryside and easy driving.

[ScreechHawk]

Thanks to both of you. My wife and I are in Brooklyn now, but both are rural residents originally (Upstate/Western NY), so we're looking for easy-going small towns with friendly neighbors, and OK with winter conditions. Thanks for the confirmations and opinions of your own. Will certainly make a trip soon to check out both the Berkshires and Rte. 22.

Seems that the NY side is a little cheaper in home prices, but they pay more in taxes. Is it all a wash in the end?

The whole city-data forum is great, thanks to folks like you!

[tao777]

Hey ScreechHawk,
I think living on the NY side might pan out, but then you'd have the commute into more populous civilization...
But I was just looking on a map to refresh my memory...Gosh, there are some terrific country roads I'd forgotten about, like 22 as mentioned by ontheroad, and 41 and 23 and 183 and 102...Wow. And Chatham in NY -all that area is wonderful. I was single at the time, but as a married couple, what a great place to live...and forget what I said about the commute, I had friends doing it, even in the worst storms and with little cars!
'Housatonic' was the gem of a town (or soon-to-be) that I'd alluded to, and W.Stockbridge -fantastic restaurants, chic cuisine.
As you can tell I'm enthusiastic, and excited for you & your wife!
Have fun-

[ontheroad]

Yes, I too looked at the map to try to refresh my memory about all the towns and villages on the New York side, and some are so wonderful and not talked about.

I am heading up to New England in early Spring and will try to wend my way through this old territory of mine.

[tao777]

Lucky you ontheroad! All this talk is making me nostalgic. I live only 2.5 hours away but that is basically impossible with a 2.5-year-old...

If you pass thru Lenox via Rte 7, and if you like organic/natural food (I LOVE it, like freshly juiced juices...) go to The Love Dog Cafe. (Hope it's OK to say that! I'm NOT advertising just offering kindly-meant advise!)

[ontheroad]

Thanks, tao777, I'll make a note of it--when you're on the road, you never really know in advance which road will come your way.

Originally Posted by tao777

Lucky you ontheroad! All this talk is making me nostalgic. I live only 2.5 hours away but that is basically impossible with a 2.5-year-old...

If you pass thru Lenox via Rte 7, and if you like organic/natural food (I LOVE it, like freshly juiced juices...) go to The Love Dog Cafe. (Hope it's OK to say that! I'm NOT advertising just offering kindly-meant advise!)

[Pidgett]

On the NY side, which is very UNDER-RATED, along the Mass border, you have such gems as:

Chatham--real small-town downtown, up-and-coming, modestly artsy
Old Chatham--old money, quaint, Shaker Museum, Old Chatham Goat Farm organic dairy farm, bird sanctuary
Chatham Center--cute, colonial style feel
East Chatham--great bookstore, lovely scenery
New Britain--off the beaten path, rustic yet sophisticated, splendidly isolated
New Concord--like Old C.
Austerlitz--dramatic scenery, B&B country
Canaan--Lovely homes, pastures, hills
Hillsdale--Down-to-earth, great upscale restaurant, lodging
Spencertown--Stunning New England architecture, picture-perfect

Of course, on the Mass side:

West Stockbridge--great restaurants as someone mentioned here.
Stockbridge--Norman Rockwell's town, great Inn, touristy Main Street
South Egremont--upscale feeling, great dining, boutiques
Mount Washington--stunning mountain scenery, delightfully isolated
Housatonic--a former rough mill town which turned itself around, charming
Richmond--formal, upscale, estate country

Just some ideas! Enjoy. Whether you choose Columbia County or Berkshire County, NYS and MA respectively, you can't lose.

Stuck in West Virginia, but not for long!

[tao777]

Where are you moving, Pidgett? Sounds like you've lived in the Berkshires...have you, & where?
(I don't mean to be nosy I just love hearing about my "hometown"!)