Quote Originally Posted by Crankin View Post
I wouldn't stay in Gloucester. There's good historical stuff to see/do there, but it's kind of a gritty old town...
HEY!! I lived in Gloucester for 7 years!! Sure, it's blue-collar, working class relative to the hoity-toity blue blood towns surrounding it ("Manchester-by-the-Sea" anyone?? Yeah...I lived in "Gloucester-by-the-Smell" thank you!), but it certainly has its own unique charms. And it can't help but take on a certain "gritty" persona when it's been working hard and taking names since 1623.

That said, if you want B&B's, biking, shopping, and generally hanging out in areas with awesome vibes, anywhere along the North Shore of MA or southern NH and ME will fill your bill. Strawberry Banke in Portsmouth NH is great.
Places other folks have said: Newburyport, Ipswich (try the famous clams!), Rockport. It's all wonderful - especially in the summer and fall. In many ways, I regret leaving. If only....