Begin in Historic Boston Common and drive north on I-95 to Portsmouth, New Hampshire. There you can walk the Harbour Trail between North Church and the U.S.S. Albacore submarine. Continue to Portland, where you can enjoy some downtown shopping before heading to Belfast, Maine for lunch at Young's Lobster Pound. Once to Bar Harbor, take in the coastline from Acadia National Park, and push forward to the red-and-white striped West Quoddy Head Lighthouse.