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The striking bronze statue of King Alfred the Great is one of Winchester's most recognizable landmarks, dominating The Broadway at the eastern end of the High Street near the River Itchen. Sculpted by Sir Hamo Thornycroft, the colossal, 15-foot-tall figure was erected in 1901 to commemorate the millennium of the king's death—a pivotal figure who made Winchester his capital and is credited with being "The Founder of the Kingdom and Nation," as inscribed on its granite base. Depicting a heroic, bearded Alfred in a regal stance with a downward-pointing sword hilt forming a cross, the statue celebrates his dual role as a military champion against the Vikings and an early Christian leader, all while standing proudly in the city he helped define.

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.

St Peter's Church in Winchester is a Grade II listed Roman Catholic church, built in the Gothic Revival style by architect Frederick Walters and opened in 1926. It stands as a continuation of a significant Catholic presence on St Peter's Street dating back to the Reformation, notably replacing a former chapel—known today as Milner Hall—that was consecrated in 1792 and holds the distinction of being the first Catholic church consecrated in England after the Reformation. Constructed primarily of ironstone rubble with Bath stone dressings, the church features a prominent northeast tower and a wide nave, serving as the central worship space for the Parish of St Peter and the Winchester Martyrs.

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.

Wolvesey Castle (also known as the Old Bishop's Palace) was the medieval residence of the extremely wealthy and powerful Bishops of Winchester.

a key landmark that crosses the River Itchen right next to the famous Winchester City Mill on the eastern edge of the city centre.

The Sword: Alfred is shown grasping a large, cross-hilted sword with the point facing downwards. This posture is symbolic, representing not just his prowess as a warrior who defended his kingdom against the Vikings, but also his role as a Christian leader, with the hilt forming the shape of a cross. The Pedestal: The statue rests on a large pedestal of Cornish granite, which is inscribed with just one word: AELFRED. Historical Portrayal: Thornycroft's depiction is a romanticized, heroic one—showing Alfred with a long, flowing beard—even though contemporary coins suggest the King was clean-shaven. The monument represents the Victorian-era idea of Alfred as a perfect warrior, statesman, and philosopher king.