Hob Hayward was an old Hobbit who wore the feathered cap of the the Shirriffs of the Shire. In happier times, he had watched the Hay Gate, the gate at the northern entrance to Buckland at the end of the High Hay. It was from this duty that he took his name: a hayward is an old term for a guardian of hedges and fences.
When Lotho Sackville-Baggins took over the Shire during the War of the Ring, defences were built to block the Brandywine Bridge itself, preventing entry into the Shire from the east. Hob was put on duty here, and was guarding the Bridge when Frodo and the Travellers returned. He was known to Merry Brandybuck, and it was through Hob that the four companions learned of the dreadful changes that had taken place in the Shire while they had been away.