Oct 11 is past peak color for northern New England. Woodstock VT probably meets your definition of small town feel with lots of boutiques. With two weeks, you are going to run into the Oct 20 fall events that are scheduled in different places like the Keene NH pumpkin festival. I like Keene even without the pumpkins. It's an attractive college town near the VT border. I also like Brandon VT which is small town with an artsy feel. If you drove up to Brandon and headed north you would be in farming country along Lake Champlain. You can cross over the mountains at some point and head to Woodstock or Norwich VT and then over to NH's Dartmouth College area, Hanover. I would head south on I89. Concord is a small city, also the state capital. Nice, walkable Main Street. You'll find the NH League of Arts and Crafts in its new location on S Main Street. Very upscale. Lots of coffee shops.

Head over to the coast via Rt 4, 16 which to me is the prettiest route once you get closer to the coast. The bridges over Great Bay are very scenic. You would probably enjoy downtown Portsmouth before heading across the bridge to Maine. I would definitely go as far north as Portland and spend the night or more there. Lots of restaurant choices.

Others can give you a better idea of the rest of your route.

You'll be arriving just after Columbus Day weekend but lodging may still be tough to find this late. Assume that on the weekends at least you need to book 2 day minimum in one place, and you absolutely need to do it in advance

In late october you will be in good leaf changing in western mass. With eight days you can stay in Lee, Williamstown, Amherst, Great Barrington and there will be plenty to see or hike around there. Head up to Lake Placid if you will be going to Vermont and spend a few days there. It is about 3 hours from Berkshires to Lake Placid.

Another good place is Lenox, MA. Great food there