Typically the big leaf peeping weekend in the week after you are going - but if you stick to higher altitudes and away from the coast you may get more color. BUT, this varies every year - and you should google a leaf-peeping website which will give you predictions, then actual info - on % of leaves turned by area.

Remeber the coast will be at least a couple of weeks later than inland and higher altitude.

Thanks for your quick reply. I do have a website bookmarked showing possible peaks. It seems western and central Vermont and then up to Northern Maine might be first peaks. I just don't know where to start or how long each drive will take. I can mapquest once I have a route.
I'm afraid of being too ambitious here. Both my friend and I are older so we want to
have a relaxing trip and not push it too much. We do want to come back down the Maine
coastline and stop in Portland on way back to Boston. I've studied several websites and forums
and can't seem to find a tour route.

Since you are still doing route-planning, it doesn't sound as if you have made hotel reservations. That might be tricky this late in the year.

Some years ago we followed a route that took us from Boston to Sturbridge, MA, then to Bennington VT, Waterbury, VT, and Franconia NH. From there we went on into Maine, but you won't have time for this so perhaps head back to MA at that point -- Concord is an interesting stopping place. Six days is a pretty short time frame.

The Yankee Magazine website has some recommended foliage routes (under the foliage button) with maps showing peak areas, and some other recommended drives (under the travel button). I think most of them are day-trips but they could give you an idea of what to expect.

Yes, I'm getting worried about hotel reservations after reading some in this forum.
So I need to get this planned so I can call hotels. Thanks for the info!!

thanks for the Yankee Mag info. will check it out

Unless you plan to be in the car all the time, six days is not long enough to cover MA, VT, NH, Maine, and a day or two on Cape Cod.

Agree that your itinerary, at this late date, may be determined by accommodation availability in your intended destinations.

The coast of Maine and Cape Cod and the Islands will not be problematic. You might even find shoulder/off season rates. But, there will likely be little fall color, due to their proximity to water.

If you hope to drive the most popular routes in Western MA, southern VT, Southern NH, lodging could be a serious, and/or expensive, endeavor. Same goes for the mountain villages northern Vermont and New Hampshire.

The best/most colorful foliage is in the higher elevations dense with trees.

Before you book lodging, be sure to check for nearby dining and the hours for same. In some of the smaller towns, or away from larger towns, dining is often not plentiful or open very late. You cannot count on finding chain restaurants everywhere. (In some areas, there are no chain restaurants.) And even grocery/convenience stores, if you can find one, may not be open very late. On the other hand, in some of the very popular towns, the restaurants are booked up, so you'd want to reserve.

We've had a summer without rain so there have been some predictions that color is going to be early and short. Right now there's an occasional branch or tree with some color in the central NH area. In case you get a rainy week, I think you are wise to consider some alternative ideas. Usually that's one of the major historical attractions: Sturbridge Village in MA, Shelburne Museum in VT, Shaker Village in Canterbury NH (near Concord), Strawbery Banke in Portsmouth NH. There are some goofy fun things to do like Clark's Trained Bears in NH. If the weather is good you could do a boat trip on NH's Lake Winnipesaukee, Portland ME Casco Bay or Portsmouth NH harbor or inland rivers cruise.
We just did a drive on the famous Kancamagus Hwy thru NH's White Mountains. There are some beautiful mountain vistas but I really preferred our return loop thru Tamworth, Center Sandwich (Rt 113A) and the Squam Lakes area. North Conway was packed with people (Labor Day weekend) but there wasn't much traffic outside of North Conway. Since Oct 6 is mid week that would be a good time to do that section of NH and easy to get to, a straight shot up Rt 93. Highway driving but pretty nice once you get north of Concord NH. Rt 93 goes right thru the mountains.
You'll be here for Columbus Day weekend so you might aim for a festival then. Warner NH has a foliage festival on Sat/Sun that includes a craft fair, parades, farmers market, tiny midway.
You could do a day trip to VT (unless you wanted to see Shelburne Museum). Mid-week would also be a good time to do the popular route from Montpelier to Stowe, stopping at Cold Hollow Cider for cider and maple syrup.
Actually it might be easier for you to pick accomodations and plan your trip from that. There are so many choices and options. You'll find the best restaurant choices in Burlington VT, Manchester NH, Portsmouth NH, Portland ME but you'll find very good restaurants all over. Do note that in the rural areas there might not be any restaurant at all and don't be surprised if you don't see many chain restaurants in VT. We spent a week in the Middlebury area and heard there was a MacDonald's (it's a college town) but somehow I missed it. Simon Pierce in Quechee VT is worth a visit to explore the building. The restaurant is very good (bring $$$). It's near famous Woodstock VT and the Billings Farm Museum.
If you got stuck for lodging and ended up having to stay in city like Concord NH you could easily make road trips in any direction. Concord NH to Burlington VT is about 3 hours. Concord to Portsmouth is maybe 45 minutes (Maine is north, over the bridge from Portsmouth).
Because it's a big weekend, I would recommend not going to any of the major tourist areas like North Conway or Stowe during the weekend.
Well, hope this rambling gave you some direction/ideas.

My recommendation would be to choose three areas and spend two nights in each where you can find lodging. You can get from one to the next during a day, and, no matter where you stay, there are usually scenic drives in all directions and/or beautiful circular routes. Nearly any route you follow one way will look different in the other direction. For example, if you drive east on Route 302 from Littleton to Bartlet in the White Mountains of NH, the scenery is quite dramatic in both directions. Same goes for other routes, such as Route 9 between Bennington and Brattleboro in VT.

I never worry about the weather or rain, as the fall colors are even more beautiful in the rain, or my favorite - overcast.

You can have a perfectly wonderful trip just enjoying the scenery and small villages, and without planning on any "attractions". We stop at attractions if they happen to be open and are on the way. Most are not worth going out of your way to visit.

You also don't have to travel back roads to enjoy splendid scenery. All of the main routes, even the Interstates (93, 91, etc.) have beautiful vistas along the way.