Answer 1
They didn't. The Jordan River is on the eastern border of Israel. The Ancient Hebrews entered from the South, through the desert.
(Unless you are talking about Abraham's family, in which case, they did come from the East, but the Torah doesn't mention anything about how they crossed the river).
Answer 2
Although the Israelites entered what is today Israel through the Negev desert, they actually crossed into what is today Jordan and then crossed over the Jordan from the east. (This is the "long-way 'round".) This is recounted in the early part of the Book of Joshua and they crossed on dry land, similar to the crossing of the Reed Sea.
As concerns Abraham's entry into Canaan, it is presumed that he entered Canaan via Lebanon and therefore would have been consistently west of the Jordan River.
Abraham possibly crossed the Jordan, but the Hebrews coming out of Egypt would have entered Israel through the South (the Jordan is on east Coast).Answer:Yes, the Israelites crossed the Jordan (Joshua ch.3-4).
The Land of Canaan, which was west of the River Jordan. This included, among other cities, Jericho, Gaza, Sidon, and Jerusalem.
Our tradition places the number at over two million.
Joshua and the Israelites crossed the Jordan River to enter Canaan. God miraculously stopped the river's flow to allow them to pass safely.
They had to cross many things, including the Sea of Reeds, the Sinai Desert, the Negev Desert, and the Jordan River.
Joshua led the Israelites into Canaan.
They were in Canaan (×›× ×¢×Ÿ).
All Jews (aside from converts) are descended from the Hebrews of the Bible, who at one time lived in Canaan. Later many of them migrated to Europe.
Abraham led his family from the city of Ur to the land of Canaan. Canaan is an ancient region located in the eastern Mediterranean, which encompasses modern-day Israel, Palestine, and parts of Jordan and Lebanon.
they moved to Egypt.
The nation of Israel (ישראל)
In the past: Canaan. Today: Israel.