The days are shorter so if you plan a longer ride you may need to have lights if dusk closes in or you get into bad weather.
If you are like me then you don't particularly like riding in poor weather. it makes for poor training but that is just my personal opinion.
Group riding in autum/winter is fine if everyone has full mudguards, especially a long flap on the back wheel. Without them, well, riding is frankly unpleasant.
Hence my own preference for solo training rides in this time of the year.
I can then plan to ride if a good day suddenly appears and if I ride without mudgaurds then it is just me and the bike that can get filthy.
A lot of off season training work can be carried out on the turbo but it is useful to just get a taste of road work every now and then. it keeps you in touch with the reality but not when the roads are wet and slippery. Off season training goals are not achieved with a broken collar bone or wrist if you happen to have an off on a wet drain cover or hit that hidden pothole due to the dark shadows or lying water.
A few of rules that I try to adhere to:
Wait for those days when the sun appears and the rain clouds disappear.
Take you emergency kit - in deeper winter days take 2 spare tubes if not 3.
Water bottle with a carbohydrate mix.
A route that loops around home so that you can bail out if required.
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