Jaffa Gate, Jerusalem

Known in English as Jaffa Gate, this is Jerusalem's Old City’s busiest entrance—and it knows it. Indeed, this is where traffic, tour groups, taxis, and determined pedestrians funnel in from Mamilla and modern West Jerusalem.

From the outside, it looks broad and welcoming, but once you step inside, the passage quickly narrows and bends sharply. That awkward L-shaped turn is no accident. Built in 1538 under Sultan Suleyman the Magnificent, the gate was engineered to slow down attackers and break their momentum. A stone inscription above the outer arch still records its precise construction date, just in case anyone doubts the planning.

Unlike most Old City gates, cars are allowed through here, thanks to an unusual episode in 1898. When Kaiser Wilhelm II arrived for a ceremonial visit, the Ottomans worried about an old belief that conquerors were expected to enter Jerusalem through this gate. Their solution was diplomatic engineering—a temporary breach cut into the wall beside the gate, so the Kaiser could ride in without triggering uncomfortable symbolism.

Fast-forward to 1917, and General Edmund Allenby made a point of doing the opposite. When British forces entered Jerusalem, Allenby dismounted and walked through the gate on foot, deliberately rejecting spectacle in favor of restraint.

The gate’s multiple names tell their own story. Sha’ar Yafo in Hebrew and Jaffa Gate in English recall the road leading to the Mediterranean port of Jaffa, long the arrival point for pilgrims and travelers. In Arabic, Bab al-Khalil points south instead, toward Hebron, known as Al-Khalil. One gate, three names, several directions—and a long memory of who entered, how, and why.