The Prophet ﷺ set out from Medina with over one thousand of his companions (at the time of the Treaty of Hudaibiya) and when they reached Dhul-Hulaifa, the Prophet ﷺ garlanded his Hadi and marked it and assumed Ihram for ʿUmra.
عَنِ الْمِسْوَرِ بْنِ مَخْرَمَةَ وَمَرْوَانَ قَالاَ خَرَجَ النَّبِيُّ ﷺ مِنَ الْمَدِينَةِ زَمَنَ الْحُدَيْبِيَةِ فِي بِضْعَ عَشْرَةَ مِائَةً مِنْ أَصْحَابِهِ حَتَّى إِذَا كَانُوا بِذِي الْحُلَيْفَةِ قَلَّدَ النَّبِيُّ ﷺ الْهَدْىَ وَأَشْعَرَ وَأَحْرَمَ بِالْعُمْرَةِ