So for the past month I've been cycling indoors for about an hour a day on rollers with no pain. This weekend I decided to ride outside in the cold (3 hours, 50 miles) and today (2 hours 30 miles). After both rides I had sudden knee pain. The knee is tender on the medial-top side, only a minor pain. However, before icing the pain can be felt from the top to bottom of the medial side of my knee. When moving the knee the pain can be pretty discomforting and can be described as stiff.

There has been absolutely no changes in my bike fit or equipment. I did not have this pain at all in the past seasons. Anyone have a clue what this may be from? Or what it may be? It has me a bit worried considering the collegiate season begins in 4 weeks.

Time for an MRI.

Could be the adjustment from rollers (little resistance) to real conditions (lots of resistance).

Is it actual pain or just pressure?

Actual pain. Hurts to extend and bend my knee.

3 and 2 hours of high resistance, the cold and jarring vs 1 hour a day on rollers. It's pretty obvious. I rode my fixed gear with 49 X 19 over an 1100 climb in 5 miles and I was stupid enough to ask my wife why does my knee hurt. She looked at me as if I was ********.

you should know the drill: call primary care doctor, schedule appt asap, have him/her refer you to orthopedist & get you checked out. not a single one of us (& possibly not even your primary care physician) can give you expert advice on these things.

that said, get off the bike for at least a week and do your stretches. if you are not warming up before your ride, this may be a cause as you are ramping up your effort quite a bit. as for your collegiate season, well, your situation is definitely better than mine: i went home for x-mas, so no biking for 10 days, biked 3 times after getting back, injured my knee on the 4th ride, and have done 1 painful 30 miler & 1 hour on rollers since the injury one month ago. get well soon

Yep off the bike asap. If it doesn't feel muscular, try some short stints of ice on the area to see if that helps to temporarily relieve the pain. Also try some nsaids (aleve) to see if that can take down the inflammation of the area. schedule appt soon as possible to have it assessed.
i had pain similar to that when i tried to jump up a classification in my club on a hilly ride. Both my knees started hurting that day, 3 days later I could barely walk it hurt so bad. I went to a chiro in the club for a fit 2 days after that . Now I have regular stretches and exercises to do, had my cleats adjusted, and some spacers put on my pedals to move them outwards. Sometimes all it takes is stepping up the intensity for your body to tell you it is displeased and cannot do that level without some modifications to fit, posture, etc.