This painting from the winter of 1913–14 was a gift from to his parents in Owen Sound. Tom’s motivation to “record” this particular observation –the wind and the cloud structure. This record is all about the wind with the side story of Tom’s passion for paddling.
The canoeist that Tom uncharacteristically included in this painting has a strong headwind. The substantial cargo is stowed well forward while the canoeist paddles from the stern seat. This bow weight was making it possible for him to sit in the stern and paddle into the wind but still keep the canoe going forward. If there was no bow weight, the strong winds would spin the canoe around like a wind vane with the pivot point situated at the heavy and unbalanced canoeist. The load may balance the canoe but the extra horse power of a bow paddler would have been nice to have in this situation. Forward progress would be a tough thing to achieve alone. This is kind of a metaphor for the art world..
From the Beaufort Scale and using the interpretation of large waves and many white caps on those waves, an estimate of a Force 5 wind and 17 - 21 knots would seem reasonable. The wave action on the bow is significant but certainly not scary.