I know you all must get tired of critiquing itineraries but I've done so much research I've just confused myself. My mother and I will be flying into Boston, mid Sept. (understand too early for leaf season). We have 10 nights, 10 days. The original goal was to see Newport, RI as well so need to leave that as a must (besides I've paid a deposit to a B&B).

I would love to see Vermont, but realize we don't have time to go further than Woodstock. I'd also love to see the Berkshires. Is this itinerary too ambitious--too much driving? Background, my mom is 76 and more active than people half her age. She likes antiques, I can handle them for about an hour. We both like country backroads, inns, stores, museums, farms, mansions, factory tours. No outlets. Looking for reasonably priced places. I've researched places to stay in just about every location, so I don't think that will a problem.

Here's my plan, but like I said, I'm thinking I should maybe narrow it down. Days 1-5 are pretty firm.

Day 1 (Wed) Arrive BOS 8 p.m.
Day 2 (Thurs) Boston (tickets to Wicked)
Day 3 (Fri) Boston
Day 4 (Sat) Boston then mid-day p/u rental car & drive to Bristol RI. Stay in B&B
Day 5 (Sun) Proceed to Newport, RI stay in Middletown
Day 6 (Mon) Continue touring Newport. Late afternoon head toward Berkshires but stay in Sturbridge or Springfield.
Day 7 (Tues) Continue on to Stockbridge, Lenox. Visit towns. Drive to Williamstown to spend night.
Day 8 (Wed) Drive to Deerfield to visit Historical houses, Yankee Candle Outlet. Hotel in Deerfield or Brattleboro?
Day 9 (Thurs) Proceed to southern/central Vermont stay in Woodstock or perhaps south of Woodstock?
Day 10 (Fri) Explore Woodstock area (want to see Billings Farm), stay in same accommodation as Day 9
Day 11 (Sat) Make our way back to Boston via I-89 to 93. Flight leaves at 6 p.m.

I think this has us driving about 525 miles in 8 days. Comments, feedback or suggestions will be appreciated! Then I need to start booking rooms. Thanks.

We are also interested in going to the Berkshires next spring. Our son lives
in Manchester, NH, so we would like to visit him and also go to some other places in the area. Is there enough in
the Berkshires to see and keep us busy for a week?

We rented a house in the Berkshires for months and there was always something to do
Williamstown is worth a full day, the Clark Museum, the shops the countryside..Lenox, Stockbridge etc..wonderful.
Then you have the small farmers markets, little roads that take you to interesting places...we found a goat farm that had a fair one time lol..lots of good goat cheese!!
Lakes and mountains ( Bish Bash Falls) .. people go there every summer for years and are kept busy.

Erin, it sounds a bit crammed..a lot of the roads you take from one town to the next are single lane country roads..you have slower speed limits and traffic and Williamstown is a bit of a drive from Lenox.

I think your itinerary is too ambitious with too many overnights close together.

For example, it's only another 35 minutes from Sturbridge to Stockbridge, so why spend the night in Sturbridge rather than wake up in Stockbridge? And, unless you are planning to visit Old Sturbridge Village (which I think is a big snooze), why stop there at all? I cannot imagine your Mom wanting to explore Old Sturbridge Village.

Likewise, Bristol and Middletown are only just over 10 miles apart.

And, Lenox is only 6 miles north of Stockbridge with Williamstown just under 30 miles north of Lenox. When we visit the Berkshires, even for just a weekend, we stay in Lenox or Williamstown and go all over.

I think your Mom would really enjoy a visit to Edith Wharton's mansion, The Mount, in Lenox, which has undergone extensive renovation in recent years.

I also think Deerfield is a huge snooze. The tours put us to sleep and we left after 20 minutes.

With your schedule, it would make more sense to head for southwestern Vermont from Williamstown, then drive back to Boston through southern Vermont (very, very scenic), perhaps spending your last night in Keene, Hancock, Peterborough or any number of towns in the area with lovely country inns, B&B's, historic restaurants.

Have a look at http://www.shelburnefarms.org/, a far more interesting destination than Billings Farm. I think your Mom would love the Inn at Shelburne Farms (where you can visit and have lunch, last I heard, even if you don't stay there). The setting is stunning.

I also think that you're moving around hotels/inns too much. For 10 nights, you want to be in 3-4 places max.

Bristol has a couple of nice houses/gardens to tour--Blithewold is one, I forget the other one I saw.
I assume Middletown is just a less expensive place to stay? Nothing there, and as mentioned, it's manageable from Bristol to Newport, so can you add another night to your Bristol stay?

Skip Springfield (again, is this meant as an inexpensive place to stay?) and go directly to your next real destination. Lenox, Lee and other Berkshire towns are much nicer places to stay. If you are there on weekdays, the availability and prices will be better.
If I remember correctly,Deerfield had only the Deerfield Inn, no other hotesl or inns, and it looked pricey for what it is. The historic village may still be interesting (I was there several years ago, but only scratched the surface with for an hour or so--I do mean to go back!)Still with the time you have, and all that driving, I think I would skip it in favor of other places you've listed

Brattleboro is a funky town, but somewhat "un-Vermontish". Not my favorite place to stay. Woodstock is a lovely area, but there are smaller towns (e.g. Newfane) with nice inns and more of a back roads feel.

All in all, it does seem to me that you're covering a little too much ground and staying in too many different places.
If you pick any town in the Berkshires, you can get to another.
Great Barrington is good for restaurants and shopping,Lenox has historic sites. In Williamstown, The Clark Art Institute is a must.

Southern and central Vermont will be a little more spread out, but staying in one place you can do a nice driving loop and still hit lots of stores, back roads tours etc. The Vermont Country Store in Westin is touristy, but still fun to browse through. Simon Pearce glassblowers had a studio in Windsor VT, and a store with a nice restaurant in Queeche (near Woodstock)

Hope this helps rather than confuses! I would do a route more like:
-Boston
-Newport(because you've already booked Bristol) then backtracking a little)
-Berkshires
-Southern/Central Vermont
and back

Just got back from the Berkshires today, and I agree there is so much to do there. I've been going for long weekends for a couple of years, and still haven't done all I iwant to! It has the greatest combination of culture and scenery.

Agree with the Edith Wharton house (The Mount), and also would add: Naumkeag (summer "cottage" of a lawyer, on an amazing property, be sure to walk down the famous art deco stairs and then look up); Chesterwood, the home of the sculptor of the Lincoln Memorial, also on a beautiful property and the house is beautifully scaled and the studio including his early models of the Lincoln sculpture; and the Freluyingenheusen (sp?)-Morris House, the home of Cubist painters.

Each house has about an hour tour, and each is totally fascinating. Not dusty history, but magnificent properties with interesting stories about the inhabitants.

museums include Norman Rockwell in Stockbridge, the Clark Art in Williamstown and Mass MoCa in North Adams.

I think you have too much hopping around as well, but not necessarily covering too much geographical distance, as these are not large states.

Definitely skip Springfield, it's just a big not terribly attractive city, I can't imagine stopping there on a vacation(believe me I went to college there for 4 years). Why not head straight for the Berkshires and park somewhere central for 3-4 days and tour around from there.

Deerfield maybe worth a quick drive thru if you really want, but certainly not a destination in itself imo.

Now Brattleboro, on the other hand is one of my favorite places. I lived there for 7 years and loved every minute of it. I'm not sure why you're wanting to get up to Woodstock (never been myself) but Brattleboro would make a great base for touring southern Vermont. The drive out route 9 over towards Willmington and Bennington is magnificent and right close by.

I think checking in and out of 6 different places (if I'm counting right) is just too much of a hassle for an 11 day trip.

If you are going to drive from Vermont back to Boston on the day of your flight... remember to leave plenty of time. It's not all that far but you could hit a traffic snarl up somewhere along the way. That would give me an anxiety attack about missing my flight.

I will admit a bias to southwestern Vermont, but if you can do it I suggest you go north on US 7 from Williamstown and north to Manchester, Vermont, then east on VT 11 towards Woodstock -- return to Mass. via Brattleboro later, if you wish. VT 7 is a truly scenic highway and the valley of SW VT not to be missed - prettier than the Connecticut River Valley to the east. In Bennington, there's the small but interesting Bennington Museum (Grandma Moses is a feature), the old church with Robert Frost's grave, the pretty village of Old Bennington and its Battle Monument. Leaving Bennington, follow the signs for Historic 7A North which is more scenic than "new" US 7, which just cuts a swath through the forests with few vistas. The village of Arlington on 7A was home to Norman Rockwell (before he moved down to Stockbridge -- Arlington folk were the subjects of his famous "Four Freedoms" paintings) and other artists. Manchester Center at Jct 7A and VT 11/30 is full of the outlets you don't want, but just before you get there you pass through genteel Manchester Village with its classic Equinox hotel and a few classy shops. Leaving Manchester on VT 11 East will take you gradually up and over the Green Mountains with some beautiful scenery along the way.

Bookmarking.

I knew I could get help and good feedback from this post, thank you everyone! OK, sounds unanimous that I've got too many different overnight stops. I did that because I didn't know how tired we'd be after touring all day and yes, some of the stops were just less expensive places to sleep enroute (i.e. Springfield or Sturbridge, I had no thoughts of spending any time there). The stay in Middletown, RI is free--using Hilton points--so Janie you figured that out.

Shelburne Farms/Museum is the original attraction that started my desire to visit Vermont. I know we would both love it, but I ruled it out as just being too far north for this trip with the short amount of time. I've been using Mapquest and just looking at driving time rather than the miles. I keep having to remind myself that it's likely going to take us longer than thought to get around.

OK, so some of you think Deefield could be skipped? Maybe we'll have seen enough historical houses in other places, so you're likely correct. Skatedancer, your comments on the houses to visit in the Berkshires has me sold.

I reserved GPS on the rental car, do you think it will work for the most part? I even thought about not pre-booking places to stay during that midweek time and just wait to see how things go when we get there. So far availability is not a problem during the week in either the Berkshires area or Vermont. The only day I've already found some sold-outs is the last Friday, so that's a sign I need to book that night ahead.

Suze, you are right that we need to allow plenty of time to make our way back to BOS. I already know my mother will start getting anxious around 8 a.m.! Have to say I'm a tad nervous about easily getting ourselves back to the airport. But it's a Saturday so I'm hopeful it won't be as bad as what I've read about driving in Boston.

OK, back to the drawing board for me. Oh to be retired so I wouldn't have time constraints--then I could actually stay at places for R&R.

I don't think leaving a couple nights open, without reservations, would be a terrible problem in this area as long as it's not the height of summer or fall foliage season.

I realize you were just looking for a place to sleep, but understand that when you say "Springfield", that means getting off the freeway, finding your way around a strange city, parking, checking into a hotel, finding a place to eat, checking out the next morning, finding the freeway again, etc. I think this is a waste of time on such a busy trip. Better (just my opinion) to continue on and stay in or near the places you actually want to see, or at least someplace nicer. Northampton, Amherst, Deerfield area is only 1 hour more north from Springfield, just an example not specifically suggesting them, but towns that are soooo much prettier.

I never used a GPS so have no idea.

But this route you're proposing is not at all difficult. You will be able to navigate using a simple old-fashioned paper road map. (There's not all that many roads around to choose from, easy to figure out.)

Hi Erin, me again

Here is my favorite restaurant in Brattleboro. Even if you don't stay in town, it is easily reached from the highway (there are 3 Brattleboro exits). It's called The Marina.

www.vermontmarina.com

In my excitement helping with your itinerary details (just kidding a little), I've forgotten to say how BEAUTIFUL, gorgeous, stunning, this entire area is. I hope you have a wonderful trip.

p.s. Northampton is a good town to stop for lunch and shopping if the timing happens to be right. Just park along the main street.

Skatedancer, we were in the Bershires this past weekend too, specifically Williamstown. Seems like we're always following each other. Went to the Clark and saw the Monet exhibit, what a great musuem, highly recommend it. Also had two great dinners, one at Gramercy Bistro in N. Adams and the other at Gala in the Orchards Hotel.

If you want to focus on historical homes/mansions, etc., and enjoy art, I would recommend heading straight for the Berkshires from Newport.

As mentioned, there are so many terrific places to visit. The Norman Rockwell Museum, Chesterwood, Naumkeag, The Mount, Sterling & Francine Clark Institute. And all would be manageable for your Mom.

If you want to economize on lodging, Pittsfield, MA is well located and one of the few towns with chain hotels/motels.

While mid-September is just ahead of the foliage crowds, I would recommend making reservations you can cancel. It's better to have them than not. Last minute will severely limit your choices (the moderately priced places fill up first). The area could be quite busy with folks visiting between the Tanglewood and foliage seasons.

From Pittsfield to Shelburne Falls is just over an hour driving. The scenery is spectacular. And, there's lots to do/see along Route 7 in Vermont. Hildene, Robert Todd Lincoln's home is awesome, for example.

Woodstock was not one of our favorite destinations in Vermont. Lodging and dining are limited and pricey.

The drive from Shelburne Falls or Burlington to Boston is about 3-1/2 hours.

I, personally, would spend the last night much closer to Boston. Driving into Logan on a Saturday is not nearly as difficult as a weekday, but it's not necessarily clear sailing either. You would want to allow lots of time.

You could spend your last night in Manchester, NH, just off I-93 (which takes you to Boston) where there is terrific dining and a huge array of moderately priced lodging. From Shelburne Falls to Manchester is about 3 hours. The drive to Logan is theoretically under an hour. On a Saturday, you probably wouldn't hit any major traffic or slow-downs until you are approaching the downtown turns to Logan, if any.

I enjoy the outdoor concerts at Tanglewood and Music Inn (are they both still around?). Wonderful to do if there happens to be something going on during your visit to the Berkshires.