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The Dipylon (, "Two-Gated") was the main gate in the city wall of Classical Athens. Located in the modern suburb of Kerameikos, it led to the namesake ancient cemetery, and to the roads connecting Athens with the rest of Greece. The gate was of major ceremonial significance as the starting point of the procession of the Great Panathenaea, and accordingly it was a large, monumental structure, "the largest gate of the ancient world". Erected in 478 BC as part of Themistocles' fortification of Athens and rebuilt in the 300s BC, it remained standing and in use until the 3rd century AD.
The gate was not only the principal gate for the city's communication with the rest of Greece—with roads leading both north to Boeotia and south to the Peloponnese, but also played an important part in the city's rituals, as the starting point (along with the adjacent Pompeion) of the ceremonial procession to the Acropolis of Athens during the Great Panathenaea. Outside the gate lay the Kerameikos cemetery and specifically the Demosion Sema, the state cemetery where the city buried its most honoured citizens. According to the 2nd-century AD writer Lucian, the walls of the gate were written over with graffiti such as love messages.
In its original state, it comprised a set of double gates set further back from the line of the walls, so that a square court was created that, covered by the walls and four towers set in its corners, served as a killing ground against attackers. The gate received its name in the 3rd century BC; before that—possibly in combination with the nearby Sacred Gate—it was known as the Thriasian Gates (Θριάσιαι Πύλαι), as it led to the Thriasian Plain. Repairs to the fortifications in the Kerameikos were carried out under Demosthenes after the Battle of Chaeronea in 338 BC, but the wall and the Dipylon suffered heavy damage in an earthquake in subsequent years, so that they were rebuilt, following the original outline, in , when Athens was under the control of Demetrios Poliorketes. In 267–262 BC, Athens participated in the unsuccessful Chremonidean War against Macedon; lead tablets with the mark and price of horses and their owners that date to this period, probably a record of the Athenian cavalry, have been found in a well at the Dipylon.
In 200 BC, however, when Philip V of Macedon attacked Athens, the fortifications of the Dipylon helped the Athenians fend off the Macedonian king. In late Hellenistic times, a second wall with a double gate was added at the outer side of the court, thus creating a fully walled-off enclosure. The walls could not hold off the Ancient Rome general Sulla, however, who in 86 BC sacked the city. Plutarch reports that the slaughter in the city was so great, that "blood flowed through the gate and flooded the suburb". The wall was repaired soon after, so that the city was able to withstand the attacks of Quintus Fufius Calenus in 48 BC. In the Roman Empire, the city experienced a revival, and potters and metalworkers settled in the buildings around the Dipylon. During the long Pax Romana, the walls were allowed to fall into disrepair. With the onset of the barbarian invasions in the 3rd century, Emperor Valerian () restored the city wall, but this was not enough to prevent the sack of Athens by the Heruli in 267. In its aftermath, the city contracted to a small fortified core around the Acropolis of Athens, but gradually recovered and expanded again during Late Antiquity, so that Emperor Justinian I () restored the Themosticlean Wall. Shortly after, however, the Slavs invasions began, and the Dipylon and the entire area were abandoned, fell quickly into ruin, and were buried.
Archaeological excavations in the Kerameikos area began by the Greek Archaeological Society in 1870, under St. Koumanoudis. At the time, the site was covered by up to 8 m of soil. Since 1913, excavations in the area have been conducted by the German Archaeological Institute at Athens.
Archaeological evidence shows traces of later repairs, possibly under Conon, when the pedestal was covered with flat limestone blocks. Parts of the Themistoclean wall are preserved only between the northwestern and southwestern towers, but the towers themselves preserved several Archaic Greece funeral monuments that were used as spolia during their construction, and were recovered by archaeologists. The existence of two gates in the wall already during the Themistoclean phase is confirmed by preserved cart grooves; the southern gate is also crossed by a broad canal, which went parallel to the southern wall and then turned south, probably joining the Eridanos river nearby.
The proteichisma comprised an –high wall, placed some in front of the main wall. As the ground sloped heavily between the two walls, the space had to be filled in, thus creating a flat surface that served as a ring road, that in the 4th century ran around the entire circuit of the wall and was used to connect the various quarters of the city. Following the reconstruction of the walls in 307/4 BC, however, this ceased to be the case, as the proteichisma received a roofed chemin de ronde, blocking the road. The late 4th-century BC proteichisma was built of fine ashlar breccia masonry.
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