How about this
route and
anchorages:
Toms River to Manesquan Inlet outside to Statue of Liberty (don't know about
depth and bridge clearances)
Statue of Liberty to Norwalk Islands (time Hells Gate so as to not buck current)
Norwalk to Connecticut River, pick up free
mooring in North Cove
North Cove to
Newport, RI
Newport to Lake Tashmoo on Martha's Vinyard
Lake Tashmoo to Chatham
I have anchored in all of these spots and most are well protected in normal summertime conditions. This
route and
anchorages don't include some really nice stops, like Hadley Harbor near Woods Hole, but does meet your 40-60 mile day criteria.
You can do the north shore of
Long Island but the ins and outs seem longer to me. But if you have the time Sag Harbor, Block Island are nice stops.
Plot the route on Active
Captain and use it to find
fuel along the way.
David