Next section hike advice needed

[joec]

Every year I go on a solo and have my wife and two young adult daughters meet me on the last day and hike into a trail town. To reward them we go to a nice resort or bed and breakfast and enjoy the town. Next trip we will go north of Maryland and do this hike. Any advice on a good town to hike into and explore? It will be next summer before we go again.

[rafe]

Massachusetts has a number of small towns more or less on the trail -- Cheshire, Dalton, North Adams/Williamstown. In particular the latter has the Massachusetts Museum of Contemporary Art (Mass MOCA) which is always entertaining.