Pennytree is a village in the riverlands, located north of the Red Fork in the disputed border area between Stone Hedge and Raventree Hall. The surrounding lands have frequently changed hands in the ongoing conflict between House Bracken and House Blackwood.
Pennytree is situated near the Widow's Wash between two grassy hills known as the Teats. It is named for a huge old oak tree that grows by the duck pond, to which hundreds of copper pennies have been nailed. The village holdfast, as strong as any in the riverlands, has thick stone walls twelve feet high, behind which the people of Pennytree retreat at the sign of trouble.
The hills to either side of Pennytree were historically known as the Teats. King Aegon IV Targaryen dubbed them Barba's Teats in honor of his mistress Barba Bracken, the mother of Aegor Rivers. A few years later, he renamed the hills for his new mistress, Melissa Blackwood, the mother of Brynden Rivers. Blackwoods call them Missy's Teats, while Brackens still call them Barba's Teats.
The hedge knight Ser Arlan of Pennytree, a competent tourney warrior and mentor to Ser Duncan the Tall, was from Pennytree. Arlan's nephew and squire, Roger of Pennytree, also came from the village. Around 210 ᴀᴄ, Duncan the Tall had never visited Pennytree and wasn't even sure of its location.
A Dance With Dragons
Ser Jaime Lannister spends a night at Pennytree after securing the surrender of Raventree Hall to the cause of King Tommen I Baratheon. He notes that Pennytree has been burned in the War of the Five Kings, but most of its houses have since been rebuilt. The inhabitants remain wary of visitors. His scouts apprehend Brienne of Tarth on the outskirts of the village. Upon meeting Jaime she pleads for him to help her save Sansa Stark from the Hound.