Well if you have some room, I'd add a night or two in southern Maine - Kennebunkport/Ogunquit/York before heading back to boston to soak up some Maine coastline.

Sounds like a fun trip!

I agree that the coast of Maine and especially Mount Desert Island and Acadia National Park could be wonderful destinations for a few days to a couple weeks.

However, if you have a few days and are in Boston already you should definitely spend time there. Plan a day on the Freedom Trail. My wife spent a couple days on the Trail while I was in meetings. Visit the Art Museum, the Isabella Gardner Museum, take a harbor cruise, go on a whale watch, visit the Acquarium and above all eat at some of Boston's unique restaurants. But don't pass up the opportunity to enjoy Boston - a great 'walking' city that is filled with history and culture.

I originally wanted to go to Bar Harbor but there just wasn't enough time and too far to go. Whats there to see/do in that area?

Although I adore the upper coast of Maine, I spend most of my small trips in southern maine. We mostly stay in Ogunquit. We often stay here once or twice a year for a night as the depth of the tide change from this location is remarkable to watch as the hours go by. I also love walking the three mile hard sand beach and the rocky Marginal Walk.

http://www.seachambers.com/

I suggested this area as it fits in with your other travel plans. Bar Harbor/Acadia is amazing but is a long drive.

I think your itinerary is fine. Foliage should be mostly OK then. Both are very busy weekends in NH and VT so make sure you make your reservations. While the S ME coast is lovely, it's not much for foliage but there won't be much color in Boston either. However, it's a good time to see the historic sights. If you get out to Concord and Lexington, there will be a bit more color there. Each about 30-45 min west of the city. Columbus Day weekend may also be parents weekend at the Boston area colleges so again, get your reservations. I predict you will love New England!

Limited time always creates tough questions. You could leave Boston and head for Portsmouth NH and a bit of the Maine coast then take the route from Portland ME to NH's White Mountains. Portland to Conway is about an hour. Since both Portsmouth and Portland have lots of terrific restaurants, you could plan a great lunch and some walking. Both ports also offer scenic cruises. If you got an early start from Boston you could get to either place and take a cruise before lunch. Then lunch, some walking then off to the mountains.

Although Woodstock is not my favorite place because it's popular with tourists, it's a good base. There is more farmland along Lake Champlain than eastern VT so I would head in that direction to see different kinds of fall views. You might choose a destination based on a fall photograph you see posted someplace. Good website to check out is Yankee magazine's website.

Make sure to visit Simon Pierce in Quechee (near Woodstock). Lunch is a good time to enjoy the a table overlooking the river. Check the menu, it tends to be fancy and pricey (but worth it).

If the purpose of your trip is to enjoy fall foliage and visit Boston, there is no point in considering the seacoast or planning to spend time there.

You could be a bit early for color in the Crawford Notch and/or Woodstock areas, but the best way to enjoy foliage is driving all over and there are scenic drives in every direction from either of those places. Both states have toll free numbers for foliage updates with suggested driving routes.

When driving into Boston from points north, highly recommend Route 2 east, which is especially scenic, particularly when the skyline of Boston comes into view.

From Woodstock VT, you can make your way south to Brattleboro in the SE corner of the state; lots of classic VT towns through there. Brattleboro has some good eateries and cute shops (plus motel chains on the outskirts of town if that ends up being an overnight). I always recommend Mocha Joe for yummy coffee!

From Brattleboro, go south on I-91 and then you have a choice, either:
- continue to I-90/Mass Pike and head quickly east from there (just under 2 hours into Boston), or
- take the scenic MA Route 2, passing through old mill towns from the Berkshires to the Boston suburbs.

If you choose the first option, I-91 in MA goes through the college town of Northampton and other locations in the Berkshires.

If you are at all interested in seeing Concord and/or Lexington, use the Route 2 option, which will pass right through both of them. I definitely recommend a stop in at least one of them:
- Concord has Revolutionary War sites like the Old North Bridge; literary museums through the local Historical Society for homes including those of Hawthorne, Thoreau and the Alcotts; and Walden Pond, which sits on the border between Concord and Lincoln, the latter being all conservation land. Some cute shops in the center of town. (The town of Lincoln has a lot of conservation land; if the fall foliage colors have made it that far south by the time of your trip, there will be lots to see there.)
- Lexington Green is where the "shot heard round the world" occurred. There are more restaurants and lodging in Lexington than Concord, and it's that much closer to Boston.

FWIW, Concord is 30 minutes from Boston; Lexington is more like 20. It would only take as long as 45 minutes if you're unlucky enough to be on Route 128 or Route 2 at rush hour.