Our record of hospitality dates back to the 1860s when Thomas Aitken, who journeyed from his home in Scotland’s Shetland Islands in 1860, first received visiting sportsmen as guests.

Where we began. Thomas Aitken’s original Muskoka property was designated for farming, but when the land he purchased, inland from Windermere, proved to be less productive than expected, he moved to the Lake Rosseau shoreline where Windermere House now stands. When business outgrew the accommodation he used for fishing parties, he built the structure that now houses the dining room.

How we grew. As steamboat services expanded to provide two calls each summer day at the Windermere wharf, local tourism swelled. Within a few years, the advent of the railway to Gravenhurst provided easier transportation for visitors to the lakes.

In 1883… a new front section was added to the popular resort that included the now-famous flag tower peak, and by 1887 Windermere House began to look like the resort it is today, with a three-story wing facing Windermere Road.

An integral part of the local community, and key employer for residents, by the 1890s, Windermere House accommodated 220 guests, and a night’s stay cost $1.50, with special rates for families. Guests’ leisure hours were spent playing tennis, croquet, and lawn bowling. Through the early 1900s, Aitken extended the front wing; built a second tower; added lighting even before the hydroelectric grid was established; and innovated a method to pump water from the Windermere Wharf into the burgeoning hotel.

In 1919… a portion of the original 200 acres was sold to the newly formed Windermere Golf and Country Club, adding an integral leisure activity for hotel guests. And after Thomas Aitken’s passing the same year, his son Leslie and daughter Gertrude took over the responsibility of hotel management, while Thomas’s wife Elizabeth continued to help until her death in 1936.

By the 1930s… the Aitkens replaced the two-story wooden verandah with stone; took the opportunity to add to the stone sunroom, coffee shop, and beauty parlour by incorporating elegant arch-transom windows; and, in 1933, built what was considered a modern new kitchen. After World War II, the first and second floors were renovated to create larger suites with private bathrooms.

Mary-Elizabeth Aitken, granddaughter of founder Thomas Aitken, eventually became the driving force for change at Windermere House. An astute businessperson, she reshaped the resort to endure, including adding a liquor license at a time when the issue inflamed passions in the community; and opening the terrace, with ten modern bed-sitting rooms named after the Canadian provinces.

Modern history… On February 27th, 1996, Windermere House was destroyed by fire during the filming of the Hollywood film The Long Kiss Goodnight, with only the stone verandah remaining intact. The Lady of the Lake was immediately rebuilt in the image of its former historic glory, using much of the original stonework, and was ready for guests in the summer of 1997. In 2007/08 major renovations created an even more enhanced experience for hotel guests.

Today… Under new ownership, improvements and expansion to the resort continue. It’s our intention that Windermere House retain its traditional charm for years to come – with a focus on modern luxury, and service excellence, for our guests of today and tomorrow.