16 Essentials for Winter Island Living

1.Two words - muck boots.
2.Two more words - down vest for the shoulder seasons.
3.A good wool hat - repeat, a good wool hat. Turns out your mother was right.
4.Scarf around the neck at all times - cold+high dew point = bone-chilling misery sliding right down the front of your coat if you even let in one centimeter of air space.
5.Outdoor clothing is your fashion statement. No one gets to see your street clothes in the winter.
6.Know the weekly specials at the restaurants. You can conceivably eat two-for-ones and low price specials almost every night of the week.
7.Know when said restaurants go on winter hiatus - there's a period in March where almost EVERYONE is closed - memorize and prepare!
8.Taste the clam/seafood chowder everywhere. Memorize restaurant recipe peculiarities. Guests want to know where the best chowder is; you have to be ready for thick/thin/potatoes or no/bacon or fatback controversies.
9.The Newes has good hard cider and a warm fire going all winter.
10.Pick up your mail. When you are used to having mail delivery, a post box or a lockbox can really screw you up.
11.Keep A ferry schedule handy at all phones, in all cars, in all purses/wallets. You never know who you have to pick up and when. 
12.Be sure to get off-island at least once - if just for practice driving the speed limit. Sucks if you don't. It's like trying to play the kids' damn car video games, only for real. Be sure to do all you can to get preferred listing at boat reservation office - this is essentially a gold ticket for anyone else who doesn't live here. Non-transferable; guard number with your life.
13.Know the intricacies of home heating system before that one cold day when it decides to do something novel like quit. And it will. 60 degree bedrooms can be remedied by flannel sheets and converting to a family bed with the pets. Don't under any circumstances let the rescue dog hog the middle. She will be hard to live with after.
14.Memorize donut list at Humphrey's and Dippin' Donuts. Get there before 7.
 15.Coffee consumption goes up as the temperatures go down. Invest in a Keurig. Everybody gets their own brand, no arguing over flavor merits versus ability to melt a hole in the cup.
 16.Ice melt is your friend.

Have a good one.