Some years ago we did a 17 day circuit in first 1/2 of October starting from suburban Boston to western Mass, then across VT south to north, over to NH and south to Boston suburbs again. We were looking for leaves, but wanted to see worthy local attractions too.
The sights we still talk about were: Hancock Shaker Village near Lennox, Sugarbush Farm (maple syrup) in Woodstock VT, Rock of Ages Granite Quarry near Montpelier, the VT State Capitol, Shelburne Farm & Museum, the Bread & Puppet Museum near Glover VT, the NH State Capitol, and finally Lexington/Concord Natl Historic Site. Oh, and we went through a small town in VT that had an AMAZING display of scarecrows on practically every storefront and house we passed by. We were very impressed with the artistry and ingenuity of the locals to create it all. I wish I could give you the name of the town, but alas time has dimmed my memory and our written records indicate only that it was somewhere between Middlebury and Northfield. Perhaps some VT local can help out.
We also saw a lot of outdoorsy sites like local mountains etc. Mostly they are nice, but not as imposing as scenery in western US such as you are familiar with around Bend. As others have stated, the leaf situation seems to be highly variable and highly local. We noted that it seems to be affected by both latitude and elevation. Those 3 states are compact and fairly dense with places to visit. You’ve got plenty of planning time, so do your homework and pick the things most of interest to you. Leaves will be luck of the draw. Have fun.
