A total of 1,015 Turkish Cypriots travelled to the Kokkina enclave on Monday to commemorate the 53rd anniversary of the Tylliria bombing by Turkish warplanes in 1964.
The crossing via the Limnitis checkpoint was completed shortly after 10am.
The transportation, which went smoothly involved 57 buses accompanied by an ambulance. Another four buses crossed the line with food supplies.
More people arrived in the enclave in 13 small boats, a yacht and two army vessels while Turkish Cypriot leader Mustafa Akinci arrived by helicopter.
Following inter-communal violence which erupted in December 1963, Turkish Cypriots established a bridgehead at Kokkina in 1964, providing them with arms, volunteers and materials from Turkey.
Seeing this incursion of foreign weapons and troops as a major threat, the Cypriot government launched an attack on the bridgehead. Turkey retaliated by dispatching its fighter jets to bomb Greek positions.
For three days in August, Turkish warplanes bombed the Tylliria area, hitting residential areas and a hospital. Over 50 people were killed, including 19 civilians.
The threat of a Turkish military escalation and a resolution of the United Nations Security Council calling for a ceasefire ended the standoff on August 10, 1964.
Last year, more than 2,000 Turkish Cypriots travelled to Kokkina in 113 buses to commemorate the anniversary.