Military Routes in Israel
Kadesh Encyclopedia
Yeah, that I can believe that a military commander would take such a route to Jerusalem
This relief map of Israel may help to visualize the terrain of two historically significant military routes during the time of Thutmose III.
Map of Military Routes
Wadi Ara is the much talked about road to Megiddo coming from Egypt through Philistia using the sea coast route. Wadi Ara as it runs through the Carmel Mountain range is described as rather straightforward and without any significant geographical features. While Megiddo is situated about north to north-west of the Wadi Ara, Taanach is east of it. The campaign of Shishak/Thutmose III was a multi-prong attack, first against the fortified, fenced cities of Judah:

"And he took the fenced cities which pertained to Judah, and came to Jerusalem."2.Chronicles 12:4 		Beth-horon ascent
The list of cities walled by Rehoboam includes the following:
Map of Israel Early Israel
1. Bethlehem
2. Etam
3. Tekoa
4. Beth-Zur
5. Socoh
6. Adullam
7. Gath
8. Mareshah
9. Ziph
10. Adoraim
11. Lachish
12. Azekah ... 2.Chronicles 11
 The Karnak city list includes:


1. Kadesh ... Jerusalem
36. Itmm .. Etam
67. Sk ... Socoh
110. Bt sir ... Beth-Zur

a) Etam was located about 18 km west-southwest of Hebron, 1.Chron. 4:32.
b) Socoh was located about 16.1 km northwest of Samaria, 1.Ki. 4:10.
c) Beth-Zur was located in the Judean hill country, Josh. 15:58; 2.Chr. 11:7. 		Megiddo and Taanach were principle regional cities during the reign of Solomon and the seat of a governor, 1.Kings 4:12, and on the list of Thutmose to conquer as specified in 2.Chronicles 12:4, but they were not the primary target. The primary target was `Kadesh' the `Holy City', Jerusalem as found first on the Karnak city list of Thutmose III. Since Rehoboam's palace was in Jerusalem it goes without saying that Jerusalem was already fortified.

The Beth-horon or Beth-heron ascent was the site of two adjacent towns, Lower and Upper Beth Horon, located near the border between the counties of Ephraim and Dan.[100] It is a ridge route and one of the most important approaches from the coastal plain to the central highlands and Jerusalem. It was located near the border of the lands of Joseph, Ephraim and Benjamin (Joshua 16:3, 5; 18:13, 14). Joshua pursued five Ammorite kings `by the way of the ascent of Beth-horon' (Joshua 10:10, 11). It was fortified by Solomon (1.Kings 9:17; 2.Chronicles 8:5) and is the site where Judas Maccabeus defeated Seron (1.Maccabeans 3:16, 24) and where Nicanor camped before the battle of Adasa (1.Maccabeans 7:39). It was also fortified by Bacchides in 160 BC (1.Maccabeans 9:50) and is mentioned in 1.Samuel 13:18; 1.Chronicles 7:24; 2.Chronicles 25:13 and Judith 4:4.
References:

1.) A. Mariette, `Les Listes géograhiques des pylônes de Karnak', (Leipzig, 1875), pp. 12-13: He defended `kdsh' to refer to Kadesh Naphthali.
2.) G. Maspero, `Transactions of the Victorian Institute', Vol. XX (London, 1887), p. 297: He defended `kdsh' to refer to Kadesh on the Orontes. No one could say why such comparably insignificant towns even then should be first on the Karnak list.
3.) W. Max Müller, `Die Palästinaliste Thutmosis III', Mitteilungen, Vorderasiatisch-ägyptische Gesellschaft', Vol. XII, No. 1 (1907), p.8
4.) A. Jirku, `Die ägyptischen Listen der Palastinensischen und Syrischen Ortsnamen', in Klio Beihefte, XXXVIII (Leipzig, 1937).
5.) J. Simons, `Handbook for the Study of Egyptian Topographical Lists Relating to Western Asia', Leiden, 1937.
[100] For a drawn map see Abraham Malamat, How Inferior Israelite Forces Conquered Fortified Canaanite Cities in BAR, Mar/Apr 1982, p. 24-35. The map is on p. 30.
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