The Bear in Maidenhead is one of the town’s oldest named inns, with records dating back to 1489, when its landlord was fined for “an unlawful price for provisions.” The original Bear stood at the corner of Park Street and High Street, serving as a central meeting and lodging spot for locals and travellers alike. Its long-standing name and reputation made it a fixture of Maidenhead life for centuries. During the 19th century, The Bear became a prominent coaching inn, catering to passengers on horse-drawn routes between London and the West Country. In 1845, the establishment moved to new premises at 8–10 High Street, the site it still occupies today. This building, with its distinctive 19th-century façade, has since earned Grade II listed status, recognising its historical and architectural importance within Maidenhead’s evolving town centre. Today, The Bear is operated by J D Wetherspoon, which reopened the pub under its brand in 2010. A major £665,000 refurbishment in 2024 modernised its interiors while retaining its period character, ensuring it remains a valued community hub. With its mix of deep-rooted history and modern hospitality, The Bear continues to represent both the heritage and the ongoing vibrancy of Maidenhead’s High Street.
