For political buffs, Dixville Notch, way up in northern New Hampshire makes for an interesting visit. This is the site of the Balsams, an old resort hotel. Here, in the Ballot Room, located on an upper floor, the first votes of every presidential election are cast just after midnight on Election Day by the hotel's staff, the only voters in the area. In the past, every presidential candidate paid a visit to Dixville Notch. The hotel closed for several years, but I believe it is back in business.
Not yet. f you want grand resort hotel, the Mountain View Grand in Whitefield, NH.
For foliage Peacham, VT, Calais, VT and in between.
Roughly follow the Bailey Hazen Military Road if you want.
Old Stone House Museum in Brownington, VT.
For cheaper lodging, the Lancaster Motel, in Lancaster, NH. Recently renovated in art deco 50s decor.
Has a bar and ask for where to smoke cigars if that's your thing.
Has a walk in humidor too.