Cold weather ends a lot of outdoor routines every year, not because the activities themselves become impossible, but because the gear and mindset adjustments needed for comfort aren't obvious until you're already cold and miserable outside.
A moisture-wicking base layer, an insulating middle layer, and a wind or water-resistant outer layer adapt to changing effort levels far better than one thick coat. Activity generates heat quickly, so starting slightly cool and shedding a layer once warmed up beats overdressing from the start.
Hands, ears, and feet lose heat fastest and are usually the first sign that a layering choice wasn't warm enough. A good pair of gloves and a hat make a bigger comfort difference in cold weather than most other single gear upgrades.
Shorter daylight hours and slicker surfaces mean routes may need to be shorter or better-lit than in warmer months. Treating winter activity as a different routine - not a colder version of the summer one - makes it easier to stick with through the season instead of quietly stopping until spring.