With a name almost as unequivocally English as “The Shire”, it comes as no surprise that Windermere was named after the largest lake in England. Windermere, Ontario, on the other hand is a small, scenic village on the eastern coast of Lake Rosseau, originally settled during the Muskoka Settlement in the latter half of the 19th century. The development of Windermere was headed primarily by three men: Francis Forge, a successful farmer and employee of business magnate Timothy Eaton; David Fife, a businessman working in the resort and tourism industry, and founder of Fife House (unfortunately demolished in 1970); and Thomas Aitkens, community postmaster and founder of Windermere House, once a prestigious boarding house, now a popular four-star resort and vacation destination. Aitken also convinced the Muskoka Navigation Company to make Windermere a port of call for the first steamboats on Lake Rosseau, the Waubamik and Nipissing, by agreeing to supply them with wood for the boilers. Windermere became an important stopping point between Port Carling and Rosseau. Forge, Fife, and Aitkens are honoured in a memorial window mounted in the local Windermere United Church for their contributions made toward the development of the area.

The Village of Windermere was incorporated on April 17, 1924. It was the smallest village in Ontario at that time. Henry Longhurst was elected reeve by acclamation. Council meetings were held in private homes or at the United Church Sunday School until 1953, when a municipal building was built.

Unfortunately, in 1996, at 127 years old, the original Windermere House burned to the ground during the filming of The Long Kiss Goodnight. It was faithfully rebuilt in the original Victorian style in 1997. Windermere is also home to the stunning and beautifully maintained Windermere Golf & Country Club.

Sample Chamber members in the Windermere area include:

• Windermere House
• Windermere Golf and Country Club
• Brackenrig Nursery and Maintenance
• Windermere Garden Centre