This article was originally published in the 2020 Spring issue of Invest In Style Magazine.
The golden age of Muskoka resorts can be traced back as far as the early 1800s and the arrival of steamships to the region. Of the classic resorts that would proliferate well into the twentieth century, only a handful still remain. Among those is Sherwood Inn which was founded in 1942 and continues to welcome guests to its idyllic setting on Lake Joseph.
Smaller than some of its contemporaries, like Windermere House on Lake Rosseau or Deerhurst in Huntsville, Sherwood Inn has always prided itself on offering a more intimate setting. Its size and setting make it a favourite for weddings and romantic getaways.
Sherwood Inn’s roots run back to a Toronto lawyer named Harry Draper, who fell in love with Muskoka during visits to his Port Severn cottage.
Along with his wife, Marjorie, Harry decided to build a resort nestled among the pines on the southern shores of Lake Joseph. Rather than compete with the massive resorts that already dotted Muskoka’s Big Three lakes (Joseph, Rosseau and Muskoka), Draper opted for a smaller scale, more akin to a large cottage estate, with all the latest amenities.
The timing of the build was somewhat peculiar, as most of North America was only starting to emerge from the Great Depression. The Depression played havoc in Muskoka, and few people had extra income to spend on resorts or cottages. Many resorts were shuttered during the 1930s and never reopened.
Despite the timing, the unique setting began to draw guests immediately and Sherwood Inn saw steady business throughout the 1940s. By the 1950s, Sherwood Inn was operating at peak capacity and new buildings had been constructed to house the Draper children, who had also moved to the property full time.
In 1960, Marjorie passed away and two years later Harry sold Sherwood Inn to Bob and Mary Pritchard.
Over the course of the next 10 years, the Pritchards added six new cottages to the grounds to increase Sherwood Inn’s capacity. Although ownership of the property changed hands several times in the following years, the resort and grounds stayed more or less the same until 1979, when Sherwood Inn was purchased by John and Eva Heineck.
The new owners transformed the resort into a year-round destination, adding a 16-room expansion to the main building, air conditioning for all the rooms, and a new tennis court.
In 1998, the hotel was sold to Clublink who continue to operate the resort. Their tenure as owners and operators nearly ended in disaster when the inn suffered a devastating fire in September of 2009. Although no one was injured in the blaze, the fire caused more than $300,000 in damage and Sherwood Inn’s future hung in the balance. A swift and comprehensive renovation ensured the inn was restored to its former glory and ready for the 2010 summer season.
Sherwood Inn continues to welcome guests 12 months of the year and stands as a reminder of Muskoka’s golden age.