• The source of the 2,000 amot and four amot measurements
• Circling or squaring the 2,000 amot
• Defining the rich and the poor of the mishna and which type of eiruv techumim is preferred
• The eiruv-maker who turned back
• How far can one go beyond the techum and still be allowed to return
• Defining the limits of a city
• Why the burial place of the patriarchs and matriarchs is called mearat hamachpeila
• The importance of proper language
• Rabbi Yehoshua outsmarted by a woman, a boy and a girl
• Advice on succeeding in Torah
• How Torah was first taught
• Rabbi Preida and the slow student
• Square, round and bow-shaped cities
• What constitutes a dwelling for extending city limits
• Astronomical calculations and squaring the city
• Extending city limits and connecting two cities

"Which is the road leading to the city?" asked Rabbi Yehoshua ben Chanania of a youngster sitting at a crossroads. "This is the shorter one," replied the lad while pointing to one road, "but it is longer. The other road is longer but shorter."

Rabbi Yehoshua decided to take the first road mentioned as the shorter one but when he approached the city he found access to it blocked by gardens and orchards. He returned to the crossroads and challenged his young guide for suggesting the shorter road which turned out to be the wrong one. "But I told you," replied the boy, "that although it is shorter in distance it is longer in reaching your goal."

The Sage was so impressed by the boys wisdom that he kissed him on the head and exclaimed, "How fortunate are you, O Israel, that all of your people, from old to young, are so wise!"

There are several explanations in the commentaries (Maharsha and Etz Yosef) of how it was possible for this great Sage to misunderstand the directions of the youngster. What is perhaps even more difficult to understand is why this story is mentioned by the gemara in this particular place.

One perspective is that it serves as a graphic illustration of how careful one must be in properly expressing himself and in understanding the nuances in the speech of others which is discussed in the previous gemara. Iyun Yaakov, however, viewed this story as an allegorical introduction to the next gemara which elaborates on the way one succeeds in learning Torah and remembering it. Torah is compared in several passages in Tanach to a road. There are people who aspire to be Torah scholars but are reluctant to invest the effort and make the sacrifices necessary for reaching their goal. They foolishly believe that there is a shortcut to reaching the "city" of Torah knowledge. Rabbi Yehoshua saw in his experience that the road which seems easier to travel is not the one which will lead him to his destination. He therefore praised the youngster for teaching him a vital lesson in life and did not hesitate to record for generations that it was a mere lad who cleverly taught him this lesson.

"Come and see how different the ways of G-d are from those of flesh and blood. A human administers a medicine and it cures one thing and can have a harmful side effect. G-d gave the People of Israel the Torah which is a life-giving medicine for the entire being."

• Rabbi Yehuda ben Rabbi Chiya
  Eiruvin 54a