Cycles of all sorts

If you use conventional pedals you'll have the easiest time choosing and setting up your footwear. If you want to go clipless you'll have to devise a way to attach cleats to winter footwear or to insulate compatible riding shoes. Many people have done this successfully.

Some riders are comfortable in a summer racing shoe with thick socks and booties, others find heavily insulated winter boots to be barely enough.

The popular SPD-style cleat (Shimano, Onza, Ritchey etc.) attaches to the shoe with two closely spaced bolts. In a soft sole these bolts don't resist the torque required to release the cleat very well. Some stiffer layer must be attached to the sole and the cleat attached to it. You canmake your own from metal or plastic or buy the adaptor made by Syntace, which is meant to attach SPD cleats to Look-compatible shoes. The three widely spaced Lookholes give good support for the cleat.

Powergrips have also been popular for Iditasport. They're available in an extra-long version for winter use.