Kalmus Beach, Hyannis
My father spent some of his childhood in Hyannis, and despite the fact that he tells me it wasn't the greatest place to grow up, I still have been able to form my own happy memories there, independent from his slightly negative association.
I think everyone can say parts of their childhood were really awful, and when people ask me for Massachusetts recommendations, I don't leap to say, "AW YEAH, you have to visit Auburn! There's the mall... the post office... the other mall..."
But that's life, right? You think your home town is really boring, you go to art school in New York City, move back to Boston, then find yourself living literally over the side of a hill from your childhood home.
That hill was the same hill Robert Goddard launched the first liquid-powered rocket, so yeah...
go Auburn Rockets... ?
;)
(* Auburn Rockets used to be the Auburn Dandies - just FYI)

restaurant in Chatham
Cook's Supply, Hyannis
Strawberry-lemonade cupcake at Cupcapes, in Falmouth
At the Welfleet-Drive-in Flea Market
Hyannisport
my favorite place to get fresh produce + Boar's Head sandwiches,
at Lambert's in Centerville
The Cape Cod Playhouse