The whole idea of changing it JUST before winter is to "flush" contaminates and HAVE ONLY fresh oil over the winter. Any riding you do after the change will add some contaminates. And even MORE SO as the weather gets COLDER.
( more by-produces of combustion are water vapor are left in the OIL ) Wait until you are done for the season, Then change your oil for storage.
Riding it in "cool" weather after the change defeats the purpose.
Even when you store your bike for winter you can occasionally fire up the bike, and let the engine (oil) warm up. This will keep water from accumulating in the oil. Why put in fresh oil before storing your rod, only to change it again when you take it out of storage?