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The Royal Oak is a famously historic pub in Winchester, often claiming to be one of the oldest in England, with its origins reputedly tracing back to 1002 AD when the building served as the residence of the Anglo-Saxon Queen Emma. Tucked away in a narrow passage off the High Street, it exudes a traditional charm with its low ceiling beams and wood-panelled walls, and patrons can even venture into a cellar area said to contain remnants of the ancient structure. The pub's current name, which appeared in the 17th century, is believed to reference the Civil War and the Royalist support shown by its patrons, and today it remains a popular spot for enjoying classic pub food, cask ales, a weekly quiz, and a hearty Sunday roast.

Winchester High Street serves as the ancient, vibrant spine of the historic city, following a route established possibly in Roman times and later formalized in the Anglo-Saxon grid, running from the River Itchen and the statue of King Alfred the Great at the eastern end, up to the medieval Westgate at the west. It is a bustling thoroughfare that seamlessly blends centuries of architecture, featuring landmarks like the 15th-century Butter Cross, the Victorian Guildhall, and the area known as The Pentice, alongside a contemporary mix of independent boutiques, cafes, pubs, and major retail chains. The upper section of the High Street is pedestrianized, enhancing its role as a central hub for shopping, dining, and cultural life in Winchester.

The Buttercross is a magnificent, many-pinnacled, 15th-century stone market cross located prominently on Winchester's High Street. Originally known as the City Cross, it acquired the name "Buttercross" because its five octagonal steps and surrounding area were traditionally used by country people to sell dairy products, eggs, and other produce. The highly decorative Gothic structure features a tall central shaft, numerous smaller pinnacles, and twelve figures, including the Blessed Virgin, various saints, King Alfred the Great, and William of Wykeham (though many of the statues were added during an 1865 restoration by Sir George Gilbert Scott). The monument is also famous for a local "small riot" in 1770, when the citizens successfully prevented a local squire from dismantling and moving the historic cross to his private estate.

Ancient Origins: The earliest surviving structure of the gate is of Anglo-Saxon character, though it was rebuilt in the 12th century and later modified in the 13th and 14th centuries. ​Military Features: The 14th-century modifications included a portcullis in the western façade and two inverted-keyhole gunports (for hand-held cannon), which are considered some of the earliest in the country. Today, the structure houses the Westgate Museum, which is operated by the Hampshire Cultural Trust.

The Westgate in Winchester is one of the city's most significant and iconic historical landmarks. It is a fortified medieval gateway that stands prominently at the upper end of the High Street, close to the Great Hall of Winchester Castle. Key Facts and History ​Surviving Gate: It is one of only two fortified medieval gateways that survive in Winchester (the other being Kingsgate), the rest having been demolished in the 18th century.

History and description of the Buttercross: https://www.cityofwinchester.co.uk/history/html/buttercross.html

There is a small museum in the Westgate, which also leads to the roof terrace with views over the High Street.

This trail is one I have been riding most weeks since 1997, like all natural trails it evolves as trees fall or new puddles form. Always lots of fun in the summer, can become hard work with mud in Jan/Feb, but usually passable. The tree felling made it mostly impassable for 2022, and then passable with care in 2023. After plenty of work from locals it became fully rideable again in the summer of 2024. The jumps closer to Winchester were built by people with small wheel bikes, they are usable with larger wheels, but check the landings before using.