This Side of Paradise - S1-E25
Plot hole: When Captain Kirk is the last person unaffected by the spores, he's on the bridge lamenting the fact that he is trapped in orbit above the planet since he can't pilot the ship alone. He also can't call for help because Lt. Uhura sabotaged long range communications. but Captain Kirk has somehow forgotten about the shuttle craft. He could have easily escaped on one of those.
Tomorrow is Yesterday - S1-E20
Factual error: Towards the end of the show the Enterprise is leaving Earth orbit and heading towards the sun. We see the Earth diminish and the moon appear looking exactly as it does from Earth. From this angle we should be seeing the "dark side" of the moon, which looks completely different. (00:40:50)
Trivia: Gene Roddenberry created the transporter as an easier (and cheaper) way of getting Enterprise crew members onto a planet's surface, rather than landing the ship on the planet.
The Corbomite Maneuver - S1-E11
Question: At the beginning, Mr Sulu calls for Captain Kirk to report to the bridge, but Kirk in sick bay does not get that message. Why?
Answer: Kirk was getting his physical and Dr. McCoy probably turned off communications, because if he hadn't, Kirk would have left and headed straight for the bridge, leaving McCoy irritated.