Cool Picture! :D
The Mad is cover-dated December, 1967, so it was probably on the newsstands in September, 1967.It's the issue that featured "Star Blecch" with art by Mort Drucker.Considering the timeframe, they were probably filming "Friday's Child" (Filmed ep 32, aired ep 40), the only episode with a lot of exteriors in the first half of the second season.
@BrittReidThanks for that. I was wondering.
Yep, that would be 'Friday's Child'.. The only other one with those exteriors in Year 2 was 'Bread and Circuses', but Kirk wore the green tunic for that.
Actually, could be 'Private Little War', since it was filmed 29 September 1967 – 6 October 1967 (per Memory Alpha..)'Friday's Child' was shot 19-29 May 1967 (again, per Memory Alpha..).