It is difficult to say without knowing his fitness level and body fat percent. But here is some simple information:

Yes, on a moderate bike ride (he is breathing rather heavily but not out of breath) he should refuel every hour.

Right after exercising, he needs to take in carbs and protein. Low fat milk (preferably skim) with some protein powder and a banana shake would be good. Your muscles are primed to take in protein but they require glucose to do that. Keep the post-exercise meal simple with minimum fat so that it is absorbed quickly.

He needs to lift weights. Men can build muscles and muscles use fat to exist. He would burn more fat at rest by raising is metabolism This is very important.

His diet is extremely important. Why burn 300 calories and then replace them with a 500 calorie ice cream cone?