Is your total trip time 2 or 3 days or is that how long you want to visit Boston? Do a search for recent recommendations. I vote for first week of October if you're going to include NH's White Mountains. Don't try to drive out of Boston on a Friday night. If you are here on a weekend, make lodging reservations ASAP. Explore Yankee Magazine's website for some ideas. Suggest an overnight in Portland ME. Some of the lobster "shacks" will still be open on weekends. If the weather is good and warm enough for a picnic table lobster that would be fun. The view at Five Islands Lobster is wonderful but you might not want to travel that far north. We have gotten decent steamed lobster dinners at Mike's Clam Shack (not really a shack) on Rt 1 in Wells. Portland ME is one of the foodiest places in the US. The food tour is pretty good - goes around the Old Port Area.
Get the wine trail maps for each New England state you wish to visit and head out for some tastings.

I really like the views as you head north on I93 thru NH. It goes right thru the mountains. You miss the view if you're heading south. So from Boston you could head north and then after the White Mountains, head east to Portland which is only about an hour from the Conway area.

You might also investigate a cheese trail. Places to find a nice selection of local cheeses would be the food Coop in Hanover or Lebanon NH (off I89 on your way to VT).

Buy a state atlas and gazetteer from Delorme. The atlases are detailed road maps. Do not trust a GPS all the time. We've had friends directed down discontinued roads trying to get to our house. In the first week of October you would also still be in good apple season. Visit some orchards. I'll nominate Gould Hill in Hopkinton NH for one of the most scenic orchard parking lots in New England. To get there using backroads, get off I93 at exit 13, heading into downtown Concord NH (north on S Main St), turn left at the lights onto Pleasant St. Continue out Pleasant St - it's also Rt 103. Get mileage to Gould Hill. The road will be on your right. You could also visit Beech Hill Farm ice cream (might be weekends only). After the orchard, return to Rt 103 and follow it thru Hopkinton, Contoocook and Warner. It will intersect with I89 at the north end of town. From there you could go to VT or head up to New London NH. On the way, follow directions to Winslow State Park in Wilmot. It's on the north side of Mt Kearsarge. Not as tall and dramatic at the auto road up Mt Washington but fun little ride. New London is a lovely college town.

well, any New Englander could go on and on. Would help to know your total time for visit.

thanks for the reply dfrostnh. We plan to spend 2-3 nights in Boston doing typical tourist stuff.That will leave us at least a week to do other stuff. Many years ago we visited Boston but stayed in an outlying area. We rode a train into town from our motel. Don't remember the area we stayed but this seemed to be a good arrangement. Any suggested areas ? We had thought about mid Sept visit. In another post someone suggested that Oct is likely past the prime time for leaf viewing. Is that correct ? Thanks again

Prime leaf colors are in October. Vermont has the most outstanding colors, red maples. Look at driving Rt. 100 through the state, S to N. www.yankeefoliage.com for info.