Set amidst the rolling tree-covered slopes of the south-west Chilterns at a picturesque bend in the river, Henley-on-Thames is best known for its attractive timber and brick buildings, its graceful 18th-century bridge, and its annual Regatta, established in 1839. The Regatta reflected Henley’s 19th-century emergence as an inland resort and fashionable social centre. But the town’s relationship with the river and the surrounding Chilterns landscape is much older and much more varied. This book traces the history of the town and river over time, from Henley’s origins as a planned medieval market town and inland port shipping grain to London, through to its 18th-century development as a coaching centre and its present-day role as a small service, tourist and commuting town. Ordinary townspeople and river-workers feature prominently, alongside merchants, landowners, and prosperous incomers. Separate chapters summarise the development of the Thames river trade, and the town’s striking buildings are fully discussed and set in context. The book draws on extensive research over several years, some of it carried out with the help of volunteers and local groups. Its broad perspective casts new light on the town and its relationship with the river, allowing visitors, residents and specialists to view it with new eyes.