We are a family of 3 (10 year old boy) driving from chicago to boston to bar harbor, maine in august. we have about 10 days and want to see nature, art (outsider, public, museums), architecture, historical sites (ancient as well as American) and anything cool along the way. Any suggestions are welcome. Thanks!
MASS MoCA in North Adams is definitely worth checking out if you can factor it into your route. It’s a fantastic modern art museum in a repurposed textile mill dating from the 1870s. You should definitely try and plan to travel through the Berkshires as well – the countryside around there is gorgeous and there are plenty of open-air venues that put on music, dance and drama performances throughout the summer.
From Boston up to Bar Harbor you could visit Salem, location of the famous witch trials and also the spot where the Massachusetts Bay Colony was first established. The driver north along the coast to Bar Harbor is beautiful – make sure you check out Rockland and its hip arts scene en route.
Have a great time.