We are going to be flying to Boston the first week of December and want to spend 4 nights in the Vermont/Berkshire areas looking to have a Norman Rockwell Christmastime experience!! Not sure which towns would be best??? Should we run around like "chickens with our heads cut off" and stay one night at 4 different locales or try 2 nights in each area?? In calling around, things seem to be booking up fast and we would like advice on upscale inns or resorts that any of you have loved in the past!!?? We love to have a good time...eat, drink and shop if that helps to narrow it down!! Sorry this is lengthy...first time poster, long time reader!!

Also, any restaurant advice would be great too!!! Thanks in advance!!!

Although you mention the Vermont/Berkshire areas. You might consider the Bedford Village Inn in Bedford, NH. Just got an email message with digital photographs from two friends that stayed there on Monday night. The photographs of the suite they stayed in are gorgeous. They mentioned that there were warm freshly baked cookies in their suite upon arrival, and that dinner at the inn was scrumptious.

You can find the website for the Bedford Village Inn by doing a search with any search engine.

On another note, I'm not sure when the tree lighting ceremonies take place in Boston, but the trees in Boston Common should have been strung with lights by then and lit. If its cold enough, you might spend an hour skating on the Frog Pond in front of the State House. Skate rental and the fee for skating is minimal.

The first week of December there is almost no chance of snow especially this year

Woodstock, Vermont and the White Mountains in New Hampshire would be excellent choices - two nights in each area? Search Fodor's back-posts for lots more info.

Not to be too cute, but have you thought of Stockbridge and the Norman Rockwell Museum?

http://www.nrm.org/

I was going to suggest the same thing. Heck, Norman Rockwell painted Stockbridge and its residents all the time--how much more Norman Rockwell can you get! The Red Lion Inn in Stockbridge appears in his painting Main St, and is located, needless to say, on Main St, Stockbridge. It's an old hotel, big firelplaces in the lobby, wide front porches with rockers, perfect for sitting and watching the Main St foot traffic (muchof it from NYC). Much to the consternation of many during the tourist season, the owners of the Red Lion have successfully fought off erecting any traffic lights in town, thinking it would detract from the feeling.

Unfortunately, at that early date, there isn't likely to be any snow to complete the picture.

Another of my favorites, a bit further north, is the Equinox Inn in Manchester, VT. This is the picture perfect New England village, and the Equinox another old elegant hotel.

Early December will be hit or miss as far as snow. Naturally, the further north , the better the odds. Here are a few towns that may meet your expectations: Stowe Vt. , Woodstock Vt,
Jackson NH, Lyme NH, Grafton Vt., Peterborogh NH. I personally wouldn't consider Bedford NH a quaint New England village - It's right outside Manchester NH, which is quite a big city, complete with shopping malls and traffic.

Thank you so much, your comments are incredibly helpful!! I checked into the Bedford Village Inn and you're right, it looks fabulous!! We may try to stay there the first night as we fly into Boston at 5:00 pm and it seems to be only 1 1/2 hours away! The other suggestions are also great, Equinox looks beautiful...the Red Lion is an excellent idea but they are sold out for the weekend due to the Norman Rockwell festival...go figure!! Does anyone have an opinion on the Cranwell Resort?? They have rooms available and it seems close enough to Stockbridge to enjoy the festivities for one night! All of the other towns/ideas sound wonderful, just trying now to narrow down the itinerary and inns!! Wish we had more time to spend, but will then drive to NYC for 5 days after our New England stay!! We'll cross our fingers for an early snowfall!! Thanks again everyone!!

Cranwell used to be a private parochial school for boys, and prior to that, one of the elegant summer homes. It's set way up on a hill with magnificent views, and has a nice golf course. My biggest concern is that it is remote--nothing to speak of around it, but then, it's not a terrible drive into either Lenox or Stockbridge from there. Probably not too much happening in Lenox that time of year, but Stockbridge is becoming a year round destination. My 2nd concern, if you are looking for upscale resorts, is that it might not be. In my mind, it's still stuck in its Cranwell school days though, so that may not be a fair assessment.

If you want very upscale in the Berkshires, you might also look into Blantyre. Like Cranwell, it sits out by itself in Lenox, and had been one of the elegant old estates, but is more upscale than Cranwell.

Have a fun trip. Everything is so close there you can easily spend a couple of nights in two different locations to see more. I grew up in the Berkshires and our lazy leaf peeping trips up to Manchester, VT around dirt roads to Grafton and back home were all done as day trips. I've since stayed at the Equinox however, and the Red Lion too, and love both old places.

If you would like to see a picture of just the scene you're trying to find, click here: http://pages.prodigy.net/redraidermom/index.html

It's just a one picture web page, a place I can shift pictures in and out, nothing to get excited about, but this was a scene in Lenox after a beautiful snowfall several years ago--probably just what you'd like to find on your trip! Double click the picture for the enlarged version.

Thanks again for all of your replies!! OliveOyl, you hit the nail on the head with that beautiful photo and thanks for your opinion on Cranwell, we will keep calling the Red Lion and see if something opens up, unfortunately Blantyre is closed during the winter because that looks very nice also!!

For something further north we are fairly set on Equinox but are looking at The Pitcher Inn, any comments?? Would it be nice to spend a night at The Mirror Lake Inn in Lake Placid or are we spreading ourselves too thin?? Still welcoming any and all opinions!!

An excellent website for "great inns" in North America is http://www.selectregistry.com/index.asp

One place that's listed with them is the Colby Hill Inn in Henniker, New Hampshire. I've only stayed there in June (once in 2000 and again, in 2002), so I can't say what it'll be like during December. The problem with New England weather is its' unpredictability. Having grown up in MA, I can say that you're less likely to have any substantial snowfall, or even any snow at all during the first week of December. Your odds increase as you head north (Vermont/NH), but don't be surprised if it's just cold.

Then again as I write this message, I think back a couple years when I flew up to visit my Mom---got stuck an extra day because of an unexpected Apr-1st blizzard ... despite Ole Richard's Almanac, you can't really predict what wintertime will bring.

Woodstock, VT is exactly what you are looking for; picture-perfect, downtown specialty shops, close to Manchester, VT upscale outlet shopping malls.
Woodstock Inn & Resort is right in the center of town facing the town "green" - upscale accommodations.
http://www.woodstockvt.com

I don't know what they've been telling you, but things do not "book up fast" in New England in early december!

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