Guided by Abdullah ibn Urayqit along a backroad unknown to the Quraysh (circling toward what is now Jeddah before turning to Madinah), the Prophet ﷺ and Abu Bakr RA avoided the main highway where the Quraysh, who had placed a 100-camel bounty on the Prophet ﷺ dead or alive, were searching for them. Suraqa ibn Malik of the Banu Mudlij spotted and pursued them for the bounty, but his horse threw him three times, after which he gave up the chase and instead asked for, and received, written protection from the Prophet ﷺ, promising not to reveal their whereabouts.
The Prophet ﷺ's only Hajj after the Hijrah, and his last, undertaken in the 10th year of the Hijrah once word went out that he intended to go. Tens of thousands of people flocked to Madinah and swelled the caravan the whole way to Makkah, so that the sahaba said they could see nothing but riders and pedestrians in every direction; it was the largest gathering the Prophet ﷺ ever addressed, and most of those present are not known to us by name. He ﷺ left Madinah on 25 Dhu al-Qa'dah, prayed and entered ihram at Dhu al-Hulayfah, and reached Makkah ten days later on the 4th of Dhu al-Hijjah, camping outside the city overnight before entering the next morning. Asma bint Umays RA gave birth to Muhammad ibn Abi Bakr at Dhu al-Hulayfah just as the caravan set out; the Prophet ﷺ told her to bathe, bandage herself, and enter ihram regardless. After performing tawaf and the sa'i, the Prophet ﷺ announced at Marwah that anyone who had not brought a sacrificial animal should end their ihram and treat their pilgrimage as an Umrah, a new and startling instruction. The pilgrims had set out with different intentions, some for Hajj alone, some for Hajj and Umrah together, and some for Umrah, and between them they performed all three recognized forms of Hajj (Ifrad, Qiran, and Tamattu'). Ali RA arrived from Yemen with sacrificial camels for the Prophet ﷺ (with those the Prophet ﷺ had brought, they numbered one hundred), and found Fatima RA already out of ihram on the Prophet ﷺ's instruction; because Ali RA had entered ihram intending to match whatever intention the Prophet ﷺ held (Qiran), he remained in ihram until the sacrifice. On the 8th of Dhu al-Hijjah (Yawm al-Tarwiyah) the company moved to Mina; on the 9th the Prophet ﷺ went on to Namirah and then Arafah, passing by al-Mash'ar al-Haram at Muzdalifah, where the Quraysh had halted in pre-Islamic times without going out of the sanctuary, to stand instead on the open plain of Arafah itself, the essence of the Hajj. He stood there in du'a from just after Zuhr until sunset before moving on, slowly and deliberately, to Muzdalifah, where he prayed Maghrib and Isha together and rested until Fajr. Sawda bint Zam'a RA, elderly and slow-moving, asked and was given permission to leave Muzdalifah early to avoid the crowds, and the Prophet ﷺ also sent the weak of his family ahead during the night, Ibn Abbas RA among them; this is the basis for the fiqh that the elderly and weak may leave before the rest. From Muzdalifah the Prophet ﷺ went to Mina, stoned Jamrah al-Kubra, and sacrificed 63 camels with his own hand (Ibn al-Qayyim observes that the number matched the years of his life) before having Ali RA sacrifice the remaining 37 of the 100. He then returned to Makkah for tawaf al-ifadah and to drink from the Zamzam water drawn for him by the Banu Abdul Muttalib. The Prophet ﷺ stayed in Mina through the days of Tashriq, departing on the 13th after performing Tawaf al-Wada' (the Farewell Tawaf) by night. Aisha RA, whose menses had begun just before entering Makkah, was told to perform every rite except tawaf; once she had purified herself and completed Hajj, she asked to also perform an Umrah like the Prophet ﷺ's other wives, and was sent with her brother Abd al-Rahman ibn Abi Bakr RA to enter ihram at Tan'im for that purpose before rejoining the caravan back to Madinah. The name "Hajjat al-Wada'" (the Farewell Hajj) was already used in the Prophet ﷺ's own lifetime: on Yawm al-Nahr he repeatedly asked Allah to bear witness while addressing the people, and the sahaba sensed, without yet grasping it fully, that he was bidding them farewell. Later writers estimated the crowd at a round 100,000, though this figure is a guess. Every hadith of Hajj fiqh in the books ultimately traces back to this one pilgrimage, since it was the only Hajj he performed after the Hijrah. On the very last day of Hajj, the 13th, the Prophet ﷺ performed Tawaf al-Wada' and, that same evening, set out on the journey back to Madinah, returning there in Dhu al-Hijjah, 10 AH. This was his final journey: once he entered Madinah, he never left it again before his death.
Years after the Hijrah, the Prophet ﷺ had told Suraqa ibn Malik, "How will you be the day that you put on the bracelets of Kisra?" After the Sassanid Empire fell at the Battle of al-Qadissiyah and Persepolis was conquered, its treasures, including the bracelets of Kisra, were sent to Umar ibn al-Khattab RA in Madinah, who seated Suraqa ibn Malik and placed the bracelets on his hands before the congregation.