You might google the following re Connecticutitchfield County, Lake Waramaug, New Milford, Bridgewater, The Boulders, New Preston, Mayflower Inn, Kent, CT. Re Vt. try Manchester View Inn. Re MA, Williamstown, The Orchards Hotel.
Yankee Magazine
Yankee Foliag.com

I'd suggest doing a loop, heading North from NYC up through central CT & western MA/Berkshires to Vermont, then head east to NH White Mtns and possibly a small part Maine before you head back south to Boston, Rhode Island coast (Newport mansions are fun to see), and back through CT coast to NYC (I presume you are flying in and out of NYC).

This way you'd hit more Northern New England on the earlier part of the trip, then head south again as the color moves South.

It was 40 degrees and chilly (despite the sun) in North/Central Vermont today. That's pretty typical. When we get rain, it's bone chilling. It's funny to me how cold 40 degrees can seem in October, yet if it hit us in January we'd be outside in tshirts.

Just to let you know too, this second weekend in Oct. is the U.S. Columbus Day Weekend holiday and it's also Canadian Thanksgiving, so it's a busy weekend. Definitely the key time to have reservations.

You must visit Vermont for spectacular colors.

Thanks guys. Lots of suggestions to discuss with our friends. I am tempted t fly back to the UK from Boston - then I can ditch the car early.

That could work too. You'd likely have to miss RI and coastal CT (unless you want to double back), but there's plenty of nice coast in S. Maine and I'd highly recommend Cape Ann in MA (north of Boston). That would also allow you a more leisurely trip through the earlier states/locations and you could visit some of those CT stops the other poster mentioned on the start of your trip.

Thanks for that. The Boss tells me that we're going for two weeks, not three. All information is valuable whan all that I have is the memory of a few places we've been before. Looking at the map gives me no clues and I guess that wherever we go it's going to be cool (what we call freezing in the UK). What I want to avoid is the situation we met last visit when we stayed at Grey Bonnet and the neaby resort was closed till Halloween.
So thanks for the guidance.
We are all getting together, over a meal, to discuss what/when/where but I am aware that we need to make reservations PDQ or we won't be going at all.
DB

David, don't worry about getting reservations right now, unless there is a very specific place you want to stay. You do have some time to plan and will find a great place.

How long do you want to spend in NYC? You could do an itinerary like this:

2 nights NYC
1 night CT
2 nights W. Ma
3 nights VT
3 nights NH White Mtns.
2 nights Boston

I'm not trying to overlook CT here. You could easily adjust this to do 2-3 nights there and not do W. Ma, or a night less in VT. The key time to have reservations would be over weekends. If you can give me more specific dates I can tell you how likely it is for the foliage to be peak where you are planning to be.

There's a lot to see in New England, but it's also small. The drive from NYC to Stowe, VT is 6 hours. So you can see if you took two days to drive there, it gives you oodles of time for wandering about, hiking, visiting little towns. The later you are in Oct. you might want to skip N. Vermont as it may be past peak, which means even less driving time.

Two weeks is still a very decent amount of time to meander about. You'll have a great trip!

I just came across this post, you might find it helpful http://www.fodors.com/community/united-states/fall-color-trip-for-4-days.cfm

Hello again LDD. Thanks for the advice - lots to talk about now.
We had a brief discussion between the four of us last night and, cutting back to two weeks we're not now visiting NY on this trip, so it's Boston in and Boston out.
We're considering leaving the UK on 5th October 2011 and having 13 nights.
I've been looking at National Parks and I don't see too many outside of NY. I was expecting that such places would be the obvious area to head to, so I will print off and re-read everyone's suggestions and start to put marks on maps of the area. Interesting that so many names in New England are close ot where we live: Northampton, Bedford, Winslow, Stowe.

Thanks again. I'll check in again tomorrow night.
David

Lookat Rt.100 in Vermont for a beautiful drive, especially in leaf season.

David, you'll find so many English names here, then repeated in every state in New England I'm pretty sure there's a Manchester in all six of the NE states (well, maybe not RI).

No, not a lot of National Parks, but a few and plenty of state parks. Two weeks in a loop from Boston will be great. You may find some of the foliage in N. New England has passed by then, it's hard to say. It's all about the temperatures and wind. It's not an exact science, so you can't plan around it. But there will still be many other places to see great foliage. And even if some of the Northern places are past peak, they are still great spots to visit.

Perhaps if you tell us more what you guys like to do (besides look at foliage) this will help. Do you like to hike? Are you interested in great food? Small, unique shops? Farmers markets and church suppers? Interesting night life? Other outdoor sports? You really can do all of this in your trip.

Hello LDD. My wife and I like a reasonable walk - circular about 8 miles is good and we don't go for seafood (which is sad for a trip to New England) but we do love a good steak. Sadly there are not many Outback Steakhouses in the area (just a few). My wife is keen to visit an Outlet Mall or two and I love taking serious photos, as does my male friend who will accompany us. Happily they enjoy a walk, too. By the time that we've walked and driven we tend to enjoy a quiet night and a beer or two. Farmers markets and church events don't do anything for us.
Thanks for the offer of even more info.
David.

Just do not miss the White Mt. area and New Hampshire. Lovely.

If you plan your day right, you could start at Tanger Outlet Mall in Tilton NH just south of Lake Winnipesaukee and end the day at North Conway's outlet malls in the beautiful White Mountains. haha There are other places for good steaks but you might have to ask on Chowhound.com. You can check Yankee Magazine's website for foliage photographs that might help you plan your route. There are many many hiking and walking trails throughout New England. You should consider visiting an apple orchard or two because fresh apples are so great this time of year and some of the orchards are in beautiful country. Some serve cider donuts and other great baked goods. Discover pumpkin whoopie pies!

Thanks both. It's starting to come together.