Harry Goatleaf was the gatekeeper for the West-gate of Bree.

Frodo and company encountered him in TA 3018, when they were asking for admittance to Bree, at which time Frodo was uneasy of Harry's appearance and tone of voice.

Apparently, Harry was spoken to by some Ringwraiths some days before the arrival of Frodo. That experience left him 'white and shaking with fear.'

In late TA 3019, a fight broke out between the people of Bree and the 'Southerners.' Harry joined the side of the Southerners along with Bill Ferny and eventually (we presume) wound up with Sharkey's men in the Shire.
Encyclopedia entry originally written by ABagginsOfTheShire