Naming places in the Bible often serves as a living monument to key historical events. The naming of this valley anchors the memory of the spies taking the massive fruit, an act that came to symbolize their entire mission, for better or worse. Geographically, this valley was likely located near the desert, sparing the spies from carrying their heavy burden across the entire land [ביאור שטיינזלץ].
The location was named specifically after the grapes rather than the other fruits they gathered, as the abnormal size of the grapes was the most striking [שפתי כהן]. The name captures the sheer power and extraordinary nature of this unusually large fruit [הכתב והקבלה]. Some explain that the location was already known by this name, and the title of a valley was newly added to it. This addition serves to praise the Land of Israel: since valley grapes are generally lower in quality than those grown in the mountains, the immense size of these valley grapes suggests the mountain fruits were even more spectacular [כלי יקר]. The name was given following this specific event to prevent a misunderstanding. It clarifies that such giant fruits were typical throughout the entire land, and the men simply took what happened to be nearby, rather than implying that only this specific valley produced such wonders [כלי יקר, מלבי״ם]. Alternatively, it was actually the local Canaanites who named the place. They were surprised by how amazed the spies were, since for the locals, fruit of that size was completely ordinary [ספורנו].
The physical effort required to take the fruit was intense; the branch was so thick that axes were needed to chop it from the tree [שפתי כהן]. Although only the spies were present, the action is attributed to the Israelites as a whole because the men acted as representatives for the entire nation [אור החיים]. The primary approach among commentators is that the naming of the place was a general, anonymous act. However, some identify specific figures behind the name. One view suggests that God Himself named the location in advance, declaring the end from the beginning [אור החיים]. Another perspective argues that the name was given by the single spy who risked his life and put in the hard work to cut the branch, while his companion, who did not value the effort, took no part in the naming [העמק דבר, ברכת אשר על התורה].
On a deeper level, the name of the place and the act of cutting the branch carry hints of the tragedy that would soon strike the generation in the desert. The name of the grape cluster echoes the concept of bereavement, foreshadowing how this event would lead to the sin of the spies, causing that entire generation to be cut off and die in the wilderness [כלי יקר]. Furthermore, the severing of the branch alludes to the eventual fate of Moses, who, as a consequence of this tragic failure, was cut off from entering the land and forced to remain in the desert with his people [נחל קדומים].