Once your choppers bike is ready, just look if it is in the top condition. You do not need to do bike maintenance on the side of the road in sub-freezing temperatures, so you can regularly do a thorough check to ensure that everything works perfectly. It is also best to go with the wider tires to avoid flats during winter. You can also try working little harder riding than to changing the flat in the cold.
Fenders are worth their weight in gold when it comes to riding in New England. Do not even think of doing a winter or spring ride without them. Even in case there is no rain, snowmelt keeps the roads wet and fenders keep the water on the road off for you. It is always emphasized on fenders that they are one of the most valuable components for staying dry, warm and even for comfort purpose. One should never forget to carry enough tools to do minor roadside repairs, tire levers, tubes, chain device, etc.
It is amazing to use choppers bike in most of the winter. A chopper bike provides more control on icy surface. It is not suggested taking your first spin on a fixer on icy roads, but once you get used to riding fixed wheel, you might find the fun behind it. With no derailleurs there is far low maintenance and there is in fact no chance of dealing with ice-covered shift cables. Many bike racers used chopper gear bikes in the winter for their training - it would as well increase your capability to spin.
At this phase winter bike is a cross frame with horizontal dropouts that would allows you to have a fixed gear, permission for studded tires and fenders, and as well braze-ons for racks. Use it both for traveling and recreational winter rides. Since it is your traveler, it has lights. This is also useful for a weekend ride, since the days are much shorter, and an even, mechanical difficulty may appear or long break could result in a ride finishing after dark. So plan well in advance if you wish to have the best winter bike ride.