We have done a couple of trips where we split the week between north and south (except in summer) which cuts down on moving to a different hotel every couple of nights. Northern VT (Burlington area) for a few days, visit Shelburne Museum on the way south and then central/southern VT. I would pick your historic places first since some might be open only on weekends in October (such as Canterbury Shaker Village just north of Concord NH). I have not been to Billings Farm Museum outside of Woodstock VT but my husband has and loved it. This is on the eastern side of VT so could be a day trip from some NH locations.

Get a DeLorme Atlas and Gazette for the state you want to visit. Every back road is documented. You still need a good road map but the Atlas shows every road including seasonal ones plus the location of covered bridges and waterfalls.

If you don't come from great apple country, make sure your visit includes a great apple orchard/farmstand. Choose one that grows heirloom varieties and, if you like to cook, plan on taking some home. Vermont has a cheese trail. Both NH and VT have some wineries you can visit. There are some farms in NH that also make cheese. The farms and orchards are usually located in beautiful country. You can probably get some ideas if you visit the Dept of Agriculture website for each state. One of my favorite summer road trips was to the Sandwich NH Creamery where they make ice cream and cheese. Absolutely beautiful country (I prefer the route just south of NH's White Mountains thru Tamworth and Center Sandwich instead of the popular Kancamagus Hwy thru the White Mountains) and a challenge to find. You might see signs about sled dogs. This is the area where sled dogs were trained for polar expeditions (Chinook Trail http://www.theheartofnewengland.com/LifeInNewEngland-Chinook-Trail.html ) Some history that a lot of people don't know about. We have not been to the Remick Museum but you might check their schedule. I've seen some interesting events scheduled there.

For Boston, I highly recommend a culinary tour of Boston's North End. We have also done the tour of China Town ending with a dim sum lunch. Both are great.

If you are in the White Mountains, then you can make a loop over to the coast for a visit to Strawbery Banke before going to Boston.

If you are in VT you could do a loop to include Sturbridge Village in western MA before going to Boston but you would want to include an overnight. Both Shelburne Museum and Sturbridge require a whole day and some people like to spend 2 days there.

Thanks so much! This will certainly help get started and tweak.
And as for apples-- we DO come from apple country--Hendersonville, NC area--but NE ones are not the same and worth a stop for.

Try the Kancamangus Hwy. 34 miles of the most beautiful colors I've ever seen. Hwy 112 between Lincoln and Conway.

Also, I spent a few days with my mother and grandmother in Tenants Harbor, MA at a B&B right on the water. It's a working fishing harbor and we got to sit on the porch wrapped in blankets and watch the local fishermen go out and come in.

Making a loop of your trip makes a lot of sense, heading north and west out of Boston into NH and VT, then south along I-91 through Brattleboro in the SE corner of VT and down to MA. If you're interested in Sturbridge Village, I-91 will take you quite close, after passing through the edge of the Berkshires and the college town of Northampton. To return to Boston, it's only a few hours on the Mass Pike (I-90) or more scenic local routes - the Pike is pretty much a straight shot to Logan. (Brattleboro and Northampton are cute towns with a number of good restaurant options in each.)

You don't say what period of history most interests you. If you like Colonial revolutionary history, you should think about a stop in Concord, MA on your return towards Boston. It's a classic picturesque NE town. You can walk over the Old North Bridge - in fact I believe there are walking trails that extend past it into conservation land, which would combine your interests! There are a number of historic sites - and walking trails - in and around Concord. I grew up in adjacent Lincoln, which has lots of conservation land riddled with trails. A walk around Walden Pond also can be very pretty at that time of year. Concord is northwest of Boston about a half an hour drive to Cambridge. If you go don't go as far south as Sturbridge, you would take Route 2 from western MA straight into Concord - with plenty of apple orchards and farm stands along the way.

Oh and I agree that DeLorme maps are great!

Fly on Southwest....book one-way tickets.....go in to Boston and back home out of Manchester, NH.

Thanks so much everyone. I am always amazed at (and so appreciative of) the generosity of fellow travelers who don't mind giving free advice! This additional info is great--esp the travel tips since I was sure we didn't have to limit ourselves to Logan R/T Pinning down history to "history with a literary twist "will help and the area around Concord would definitely fit several categories.

And an air travel question-if the leaf color pattern is from N to S is it just as easy to start in NH or VT and end in Boston?

bookmarking

Glad to help! Of course if you're looking for "history with a literary twist" and visiting Concord, you should look into visiting the Alcott house, the Old Manse, Emerson's house...
http://www.concordchamberofcommerce.org/concord_visitor-info2.htm#historical

As for air travel, it depends on what "easy" means. Since Logan is a major airport, frequency and cost of flights might be better; also more nonstops. But as far as driving goes and depending on your route, you could just as well arrive in Portland, ME; Burlington, VT; etc.

Even though it is still months away, we couldn't pass up great airfare from Asheville-Boston so took the plunge and signed on for Oct. 11-Oct. 19 and have divided the trip into 2 parts--starting in VT (Middlebury) for 4 nights, NH (N. Woodstock) for 3 and an o'night 10/18 in Boston for an early return home Wed AM. Both areas seem to offer alot of choice in the things we like to do, and even if the colors are not "peak perfect"--despite the late date--we will still see more maples than we enjoy here in WNC so we will not feel cheated.
Given such an overall short stay, we opted to not add Boston to the mix but save it for another time (possibly in spring) where we could give it and N MA the attention they deserve.

Even this early it is obvious that the serious "leaf peepers" are making lodging reservations now and since we had some definite preferences, we got ours in also at 2 reasonably-priced but very comfortable-looking B and B's.

Again--thanks to all the advice givers. Your comments have helped us plan a trip we know we will enjoy to the max.

Unfortunately, with those late dates, especially when a few days can make an enormous difference, your destinations will likely be too far north for much color. Unless fall is unusually late or lasts unusually long, you may arrive when most of the leaves have changed and fallen. One rain storm with a bit of wind wipes all the leaves off the trees just around "peak".

By then, the best color will be in the southern Berkshires, central MA and CT. Boston and vicinity may be beautiful due to its proximity to the ocean and that the leaves change there last. Or, from Middlebury, you may find some beautiful colors in Burlington/Shelburne, again due to proximity to water (Lake Champlain).

For better planning, enter your dates in this map

http://www.yankeefoliage.com/peak-foliage-forecast-map/

Good advice and certainly appreciated.

We had checked this guide but really wanted to steer clear of the Columbus Day weekend throngs as well as not going too early, We also knew we couldn't afford to wait until more precise 2011 forecasts were available.

Even though we know this late date might offer a mixed bag we will take the chance (and hope) that certainly en route (via MA) to VT and back from NH we may still get lucky for some brilliant blaze. Even in WNC when our colors are past peak they are still beautiful though in a more muted way.

Thanks!

While Columbus Day weekend is usually, but not always, very busy, I would describe it as "throngs". And, though there's more traffic, in most places you don't find endless backups, only perhaps the occasional slow-down.

There are toll free Foliage Hotlines for each state you can check for progress in the various areas. If you see glorious colors along the way, it would make more sense to head for areas that are underway versus way past. Regardless, there are dramatic drives through the mountains any time of year, even in the dead of winter (the evergreens are still all about), but they are deeper into the Green and White mountains than Middlebury and Woodstock.

You mentioned hiking. Lonesome Lake Trail in the White Mountains is a great hike. There is an AMC hut there where you can enjoy lunch before/after your swim.