The Shephelah is characterized by many furtile hills, checkered with many ruins from ancient times. There are also a lot of small natural springs, which are almost always being diverted into stone pools from ancient times. A popular and famous hobby of Israeli teens is to repair and clean these pools or even build completely new ones. Most israelis from the central regions go to these pools to relax and cool off during the summer, and during the weekends its rare to be alone in those springs for a long amount of time. Its also common to see "chill out" zones and fruit trees (especually figs and raspberries) near those springs.
The Shephelah was a main and important region during biblical times. It is the gateway to Jerusalem and other big cities in the mountains, such as Hebron and Bethlehem, and there were many important cities in the Shephelah itself, such as Beit Shemesh and Gezer.
It was also the main battleground between the Israelites, who sat in the mountains, and their arch enemies, the Philistines, a greek nation that invaded from the sea and conquered the coastal plains of Israel. One of the most famous battles in the world, the battle between David and Goliath, took place in Valley of Elah, one of two main vallies in the Shephelah (along with Ayalon vally).
During the israeli war of independence, the Shephelah was the main battleground between Israeli forces, who tried break into the road to Jerusalem, and the armies of Jordan and Iraq, who tried to reach the coastal plains and conquer the temporary capital of Israel, Tel Aviv. In the end, The line of truce between Israel and Jordan passed mostly through the Shephelah (except the road to Jerusalem). During the six days war in '67, all of the western bank of the Jordan river was conquered by Israel, including the Jordanian Shephelah and the mountains of Judea and Samaria.