We think we've come up with a pretty good "road trip", we are, however, still open to suggestions....we are traveling early December...

Day 1...Fly from west coast to Boston, arrive at approx. 5PM, drive to Woodstock, Vermont for a night at the Woodstock Inn (looks like about a 2 1/2 hour drive??)

Day 2...Drive to Manchester, Vermont for one night at the Equinox Resort/shopping/eating etc...

Day 3...Drive to Stockbridge for a one night stay at Cranwell Resort (mansion)/Norman Rockwell celebration is happening at the time we're there...

Day 4...Drive to Newport, RI for a one night stay at the Hotel Viking/evening tour of the Breakers, then dinner..

Day 5...Drive to Manhattan for a 5 night stay at the Westin Times Square, and a full schedule of sightseeing/eating/broadway shows/shopping etc....

This being our 1st visit to the N.E., we want to make sure we're not biting off too much but we love scenery and driving trips, hence the 4 New England locations!! Any advice is much appreciated!!

Can only advise about the first two segments.
Boston-Woodstock is about a 3 hour drive, depending a lot on traffic and road conditions.

Woodstock-Manchester is perhaps another 1 1/2 hours or so drive. If it's icy, be prepared for a scary, slow ride up and over Killington Mt. and Pico. Usually, this in not frequently the case in early December in Vermont, but winter has come early here this year.

Your plans look fine, but be aware that you're going to have to make some choices as to allotment of the few hours you have reserved for the two towns. If all you want is dinner and a stroll around Woodstock, and perhaps a day of shopping in Manchester, then I think you will be happy.

Thanks Vermonter for the info, we'll cross our fingers for snow, not ice!! Is there another route if the weather is dicey?? Any great restaurant suggestions would also be terrific!!

try scales and shells for dinner in Newport..it was a highlight of our New England trip.

Greetings!
Well, you do say you love driving trips! I don't think you'll want to leave the Woodstock Inn the next morning, though.
You may want to consider skipping the Equinox and Manchester if you fall in love with the Woodstock/Queechee area. Be sure to take in the Simon Pearce glass factory/shop/cafe near the Queechee Gorge.
Newport is definitely worth visiting, too. (I think I'd stick with two nights in each destination.) You may also want to investigate the winery next door in Middletown.
Have a wonderful trip!

Route 103 through Bellows Falls and Ludlow is an alternative, but then you would miss Woodstock, and it wouldn't neccessarily be an improvement driving. That area can get pretty nasty also. Let's just hope that the weather gods are with you!

As for restaurants, I don't eat out much in either Woodstock or Manchester, for some reason. Bentley's in downtown Woodstock is pretty good, and I like the Sirloin Saloon {it's a small regional chain; there is one in Manchester} for steak, seafood and salad-bar}. Perhaps others will have further suggestions.....

On your way to Stockbridge, I strongly recommend that you visit the Clark Art Institure in Williamstown, MA. Outstanding collection of French Impresionnist Paintings.

New York City is not part of New England. That being said, I would do New York first then drive to Vermont (pick one place to stay and do day trips--it's a small state), then head to Newport via Stockbridge. Whether you decide to do this itinerary or not, there are airports in Hartford (CT), Providence (RI) and Burlington (VT) that would be much better than Boston's Logan. Bradlee Airport near Hartford is about 2 hours from Woodstock and is served by all the major airlines. TF Green in Providence is also served by the majors and is not far from Newport. Burlington might work also but there is the weather factor.

I don't know if your flight plans are set in stone, but I would fly into Hartford, CT. instead of Boston. It would be easier to drive from Hartford to Vermont. Logan in Boston is such a big hassle to get in and out of.
Good luck!

Try the Prince and the Pauper in Woodstock for dinner if you arrive in time. The grub at the Woodstock Inn is so-so.

Thanks for the suggestions, unfortunately we don't have a choice of airports...we are flying into Boston on Alaska Airlines and Logan is the only choice, we then fly out of Newark back home (again, our only choice) and we already have Broadway tickets and hotel reservations for the latter part of our trip!! The New England portion is the "wild card" at the moment, but thought it would be helpful to give the entire itinerary (NY)!! Thanks again, any other ideas would be great!!

Also, we are still thinking of staying at the Woodstock Inn but in looking back at some of the older comments, some people think their rooms were not quite up to snuff...any recent visitors comments would be wonderful!! Or any other upscale property ideas!???

If the 3+ hour drive is too much the first night, you might want to consider a halfway stop somewhere in New Hampshire. There are some very beautiful towns going up I89, such as New London, Warner, or Sunapee. You also may want to consider two nights in Woodstock instead of driving to Manchester (unless you want to go to the outlets in Manchester).If the Billings Farm Museum in Woodstock is open, you should spend a few hours there, it's a great place. Realize the driving in this part of the country can get a little tricky this time of year, and distances on a map can be deceiving.

If you are arriving in Boston at 5 pm on a weeknight, the drive might be a lot longer than 2 1/2 hours. Traffic in and around the city can be awfull. I think your itinerary sounds like a lot of fun, the Norman Rockwell celebration should be a blast!

I concur with Plummie that the food at the Woodstock Inn is mediocre. Don't know about their accommodations.

Amy's right, driving IN Boston is awful. But by the timeyou get your luggage and your rental car, rush hour should be almost over. Just be sure to get VERY good directions from the rental car people so you don't get lost getting on the Turnpike from the airport. Sllow 3 hours to get to Woodstock, you won't be traveling at the speed limit at that hour of night.

Another vote in the direction of mediocre food at the Woodstock Inn...
with the accomodations to match.

Woodstock Inn is overrated and expensive, although the town of Woodstock is quite charming.

I'm going out on a limb to say I really like the Woodstock food. Perhaps not exceptional, but certainly above average! I also have no problem with the rooms. It is not brand new sleek luxury, but a refurbished inn feel in a large hotel. Plus the common areas are really lovely. It's my favorite place to stay in Vermont, and I like the inn and the town much better than the Equinox and Manchester. Just mho.
I'll second Bentley's for a pleasant dinner. I'd also recommend the Skunk Hollow Inn for dinner in nearby Hartford.
And another plug for Newport. One of my other favorite places in New England!

Thanks once again everyone!! Regarding Newport...we are having a tough time getting a room at one of the nicer inns for only 1 night (Saturday), most have a 2 night minimum, would it be convenient to stay at the Westin in Providence?? It looks like we have to drive by Providence to get to Newport so it would only be backtracking once!! We would like to do the holiday evening at the mansions then have dinner in Newport but figure we'll head to NY the next morning...any advice???

I would not stay in Providence if Newport is the objective. If you're stuck for Newport accommodations, try the Best Western Atlantic Beach Hotel. Not charming, but clean, convenient, and accommodating. BUT... are you sure you don't want to spend two nights there?

Disregard the Providence question...we got a room for 1 night at the Hotel Viking...yeh!!! We had been trying to access their website for days with no luck but I just called them and they seemed to have no problem with a Sat. only stay...woohoo!! Every other place I called was a 2 night minimum! Still debating on the Woodstock Inn/Equinox rooms so any more advice is great!!!