The Ancient Trade Route
Recall that Yosef met his brothers while they were grazing their sheep in the hilly area of Dotan (see 37:17). (See Board #1.) Recall that during their meal, the brothers 'lifted up their eyes' (see 37:25) and noticed a caravan of Yishmaelim travelling down from the Gilad (today, the northern mountain range in Jordan), on its way to Egypt. (See Board #2.)
Now, when we read this story in Chumash, almost everyone assumes that this convoy will soon pass nearby the spot where the brothers are eating. However, they don't know their geography! The caravan of Yishmaelim (camels et al) travels along the ancient trade route (better known as the Via Maris) which crosses through Emek Yizrael (the Jezreel Valley) on its way toward the Mediterranean coast. (See Board #3.)Therefore, this convoy, now descending from the Gilad would pass the cities of Bet She'an, Afula and Megiddo in Emek Yizrael, but would not pass the hilly area of Dotan. (See Board #4.)
Dotan, today the area of Jennin [z"l], is situated about 20 kilometers (13 miles) north of Shechem, and about 10 kilometers (6 miles) south of this main highway (the Via Maris) crossing Emek Yizrael. In altitude, Dotan sits about 200 meters (660 feet) above Emek Yizrael. From Dotan, one has a nice view of the Gilad and parts of the Jezreel Valley. (See Board #5.)
Hence, from their vantage point in Dotan, the brothers are able to see a Yishmaelite convoy turning down into the Jezreel Valley from the Gilad, even though it is still far away. This convoy will not be passing below their feet; rather, in a few hours it will be passing about 10 kilometers to the north. In order to meet that caravan, the brothers would have to first fetch Yosef from the pit, then take a short trip from Emek Dotan to Emek Yizrael. They have ample time to first finish their meal, go fetch Yosef from the pit in the "midbar" (on their way to the Emek), and then meet the convoy at the pass to sell Yosef for the 'best price.'