Welcome to the forum and I hope you enjoy you visit to Boston. The information that you receive on this forum is great and will lead you to some good trout waters for sure. Aside from the previous mentioned rivers, I would also do some research on the Westfield and Deerfield rivers. Fantastic bodies of water that you will enjoy in terms of fishing and scenic views(Hint: Knightsville Dam for the Westfield river
). These rivers are within 2-3 hrs of Boston and will also expose you to the "small town" aspect of Massachusetts that is often overlooked or ignored by those of us that live here. I have attached a link to the Massachusetts fishing website as requested to address any questions about licensing. See below;
However, as woodrivertroutbum mentioned, the Striped Bass fishing "should" be fantastic during your stay. Don't have any experience or equipment/flies to fish the saltwater?, no problem, I'm sure accommodations and arrangements can be made. Just let us know!
Think about it this way;
I would not recommend that you go to the north end of Boston (known for authentic Italian food) and look for a steak house no more that I would send you to Massachusetts for tout fishing during May.
Imagine fishing for trout with a streamer or any other sub surface fly.........remember that subtle take just before you set the hook?.......hoping it was a strike and not bottom....? A striper hit is like someone trying to rip the rod out of your hands! Don't miss out on the experience.
woodrivertroutbum, worm hatch? that would blow his mind!
OOOOOOPS! forgot about the saltwater license garbage. Either way fresh/salt water fishing will require a license. The website mentioned above will address both.