The tricks to driving in MA:
1. don't make eye contact
2. don't use your directionals- it's like giving away your position to the enemy
I'm in NH, and we don't have a LOT of highways, so if you do need to 'get there quicker,' you can, and not lose too much scenery.
Definitely take a ride on the Kanc...FYI it's 34 miles across with no gas stations, so don't go on an empty tank.
Most of our "attractions" are natural; grab a picnic lunch and stop if you have time.
Sorry, but the Old Man is now "off" the Mountain.
If you're into hiking, Baxter State Park in Maine offers a decent hike up Mt. Katahdin, or if you're in NH, Mt Washington is a nice drive or hike. In October, make SURE you dress for WINTER if you're going up Mt. Washington.
Wolfeboro, NH is a wonderfully quaint town with shops and little holes-in-the-wall restaurants- in the Lakes Region of NH (as is Keepsake).
If you'll be coming in early October, the Fryeburg fair is a great fair (so I hear, but I've never made it there yet). Here's a link to New England Fairs:
http://www.newenglandexplorer.com/statefairsne.htm
And if you're into yard sales, the Ultimate Yard Sale will be held on October 13 at the Cumberland Fairgrounds in Maine.