Wentwood

At just over a thousand feet, Wentwood won't give you vertigo, but it might give you a mild case of 'where’s the summit?' syndrome. It’s the remnant of a massive royal forest, perfect for those who prefer dodging branches to technical scrambles near Newport.

• •Once a vast royal hunting forest, it provided timber for the Earls of Chepstow and even the Royal Navy. It remains the largest ancient woodland in Wales, though the 'ancient' part is currently doing a lot of heavy lifting.
• •The area is steeped in Bronze Age history, featuring burial mounds and a stone circle. It overlooks the Roman city of Caerwent, which was likely much easier to navigate than the modern forest tracks.
• •The Curley Oak is one of the forest's most famous residents, estimated to be over 800 years old. It has stood its ground since the Middle Ages, which is more than can be said for most modern hiking boots.
• •In the 17th century, local 'commoners' engaged in fierce legal battles and riots over grazing rights against the Marquis of Worcester. It was effectively a high-stakes version of 'capture the flag' but played with more sheep and fewer rules.
• •The actual summit is buried deep within a dense thicket of trees, ensuring the grand panoramic reward is a stunning view of bark and pine needles. You will likely walk past the highest point twice before realizing you have already 'conquered' it.