The Canaanites, that dwelt to the mountain - The territories of the tribe of Judah lay in the most southern part of the promised land, which was very mountainous, though towards the west it had many fine plains. In some of these the Canaanites had dwelt; and the expedition marked here was for the purpose of finally expelling them. But probably this is a recapitulation of what is related Joshua 10:36; Joshua 11:21; Joshua 15:13.

Kirjath-arba

Joshua 14:15 And the name of Hebron before was Kirjatharba; which Arba was a great man among the Anakims. And the land had rest from war.

Sheshai

Judges 1:20 And they gave Hebron to Caleb, as Moses said: and he expelled there the three sons of Anak.

Numbers 13:22,33 And they ascended by the south, and came to Hebron; where Ahiman, Sheshai, and Talmai, the children of Anak, were...

Joshua 15:13,14 And to Caleb the son of Jephunneh he gave a part among the children of Judah, according to the commandment of the LORD to Joshua...

Psalm 33:16,17 There is no king saved by the multitude of an host: a mighty man is not delivered by much strength...

Ecclesiastes 9:11 I returned, and saw under the sun, that the race is not to the swift, nor the battle to the strong, neither yet bread to the wise...

Jeremiah 9:23 Thus said the LORD, Let not the wise man glory in his wisdom, neither let the mighty man glory in his might...

Tsippor
"Tsippor is the greatest city of Galilee, and built in a very strong place." "Kitron (Judg 1:29,30) is Tsippor: and why is it called Tsippor? Because it is seated upon a mountain as Tsippor, a bird." "Sixteen miles on all sides from Tsippor was a land flowing with milk and honey." This city is noted in Josephus for its warlike affairs; but most noted in the Talmudists for the university fixed there, and for the learning, which Rabbi Judah the Holy brought hither, as we have said before. He sat in …
John Lightfoot—From the Talmud and Hebraica

Judges
For the understanding of the early history and religion of Israel, the book of Judges, which covers the period from the death of Joshua to the beginning of the struggle with the Philistines, is of inestimable importance; and it is very fortunate that the elements contributed by the later editors are so easily separated from the ancient stories whose moral they seek to point. That moral is most elaborately stated in ii. 6-iii. 6, which is a sort of programme or preface to iii. 7-xvi. 31, which constitutes …
John Edgar McFadyen—Introduction to the Old Testament