What to Pack to Travel
You won't need any exotic gear for New England, but you do have some packing decisions to make.
Pack lightly if you sail aboard a Maine windjammer.
Dress & Fashion
You'll want at least one fairly nice outfit of the dress or jacket-and-tie variety for special evenings in fancy restaurants. Few establishments enforce a strict dress code anymore, but you should be prepared nonetheless.
Rain can come at any time of year. A small umbrella is minimal rain gear in summer; in other seasons a raincoat is necessary as well.
In winter, be prepared for freezing weather and snow. Full woolens and foul weather gear are required.
If you take prescription medicines regularly, bring a supply of the medicine, not a prescription for it.
Doctors are licensed by state, and their prescriptions are not accepted in any state except the one in which they are licensed. In other words, a prescription from a California doctor will not be accepted in Connecticut.
Other handy items might include a pair of binoculars and a flashlight.