Some states say you need to have 400 square inches of blaze orange. I would at a minimum have blaze orange vest, hat and GLOVES plus the pack cover(definitely don't wear white, grey or brown gloves). Personally, I wouldn't hike in Putnam County during rifle deer season, especially on the first or last day. I'm not sure how much of the trail is hunted, but I think Putnam gets lots of hunting and has lots of deer. Don't be on the trail when it starts getting dark (CT and MA go until 1/2 hour after sunset and it is
really dark by then).
Conn. might be safer because in many cases only bow or shotgun are legal; the Conn. regs are kind of complicated.
http://www.ct.gov/deep/cwp/view.asp?A=2700&Q=556888 I think rifles can only be used on private land or by landowners and opening day is not Nov. 21. You could also start in SW Mass on Sunday (no Mass hunting on Sunday) and hike south. In fact, shotgun deer season in Mass starts Nov 28 and modern rifles are not allowed. In fact, a nice hike would be to end in Salisbury, CT starting as far north as you have time for ( the Taconics in SW MA are beautiful).
Hunting safety has improved a lot, but back in the '70s when my parents lived in Greene County, NY (Catskills) there would be a hunting fatality within 10 miles of their home every year or two. So, I'm perhaps more paranoid than warranted these days.