A traveller journeying east from Michel Delving would pass along the main East Road through the Shire. While still in the Westfarthing, this was met by two smaller roads: one from Little Delving to the north, and one from Tookland and the Southfarthing beyond. Where these roadways came together, a town had grown up, appropriately known as Waymeet.
In the War of the Ring, the ruffians who took over the Shire had a staging post or barracks in Waymeet, and it was from here that Sharkey's Men set out for the Battle of Bywater, in which they were soundly defeated by the Shire-hobbits.
The name Waymeet is a modernised spelling of a name with another older form, Waymoot, which is the spelling preferred by Tolkien in early drafts of The Return of the King. Though he ultimately modernised the name within the book itself, the map of the Shire that accompanies The Lord of the Rings was never corrected, and still carries the older spelling of the name.