How about this route
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
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
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.