Jeff, I live in Atlanta so don’t know when the best time of year would be to hike Massachusetts. I would guess late September through October. The leaves would be turning colors and it would be cool hiking, even cold in some areas. The trail mileage from the CT/MA state line to the MA/VT state line is about 90 miles. Since you are both experienced hikers I would guess it would take you about one week (5-7 days) to hike the Massachusetts portion. Depending on where you live and how you would get to the trailhead would determine where you start. As gingerbreadman suggested, I also suggest S-N. There are plenty of people that can shuttle you to different sections of Massachusetts. I suggest you park your car at one end and take a bus/shuttle to the other end and hike back towards your car. There are a lot of bus services and shuttles available through MA. When you park your vehicle make sure it is in a safe location. Hiking towards your vehicle makes it easier for you. You don’t have to end your hike on a certain date or time. You can hike as fast or slow as you want. It also saves you time waiting for someone to pick you up and because it will be at the end of your hike no shuttle drivers need to put up with your smell. A couple of suggestions: check out Berkshire Bus, Peter Pan bus service, or AT shuttle list for transportation. Plan on staying one night at Upper Goose Pond Cabin. Thomas Levardi Hostel, 83 Depot St in Dalton is a nice place along with the Shamrock Motel. Dalton is a nice little town to spend the day and night. Jacob’s Pub in Dalton is very friendly to hikers. Cheshire is also a nice little town to spend the night, stay at St. Mary of the Assumption Church for free or a small donation. Mt. Graylock and the Bascom lodge is a nice place to stay, $100 for private room. If your hiking north this would be your last night on the trail. Or you can hike down to the next shelter for free. Willimstown and North Adams will be on the Vermont state line. Good Luck and congratulation on your marriage.
Bilko