Most cadets seem to agree on two things: that the weather tends to fluctuate and the winters are not fun. The weather also plays a large role in the physical lifestyles of most cadets. In the summer, you will see an overwhelming majority of cadets outside, running or playing intramural sports. In the winter, however, the weight room gets extremely crowded, and cadets like to stay inside the barracks. Dealing with the cold is just one more obstacle that cadets face at the Academy. It is by no means the hardest struggle for them to go through, but it is a consideration. On the other hand, if you like snowy white winters, the scenery around West Point can be absolutely breathtaking. Upstate New York is so picturesque sometimes.
The winters do seem to hit a lot of cadets by surprise, though. But just like anything else, if you prepare for them, they aren't that big a deal. Also, cadets don't need to worry about dressing for the weather. Central guardroom decides for them. Usually, they overestimate rather than underestimate how much you need to wear, so don't expect to be standing outside freezing to death, catching pneumonia. However, you might find yourself uncomfortably warm when it isn't that cold outside. But, then again, the Academy would never let a cadet be uncomfortably cold.