By Jerelyn Craden
Sir Sam’s Ski and Ride and its owners for 56 years – the Bishop Family — are synonymous with the Haliburton Highlands. Now, as they hand over the keys to Sir Sam’s new owners, the Wilkinson Family, Chris Bishop shares a window into the journey that led to this day.
“Seven years ago, we began a seven-year exit strategy,” Bishop said. “Our family members are all 60 and over and it was time to transition to new owners. There was a four-part plan and in the seventh year, we were able to do that.”
The Wilkinsons, who owned a cottage on Boshkung Lake for fifteen years, enjoyed the atmosphere at the ski hill and, wanting to invest in a business in Haliburton, contacted the Bishops asking if it was for sale. “Just at the same time,” Bishop said, “we were putting all of our marketing and sales materials together.” The timing was perfect.
Bishop shares fond memories growing up at Sir Sam’s as well as plans for the future; but, first — let’s take a brief look at the history of this beloved landmark, where long-held memories are cherished and new ones are about to begin.

Before the beginning …
1916 – Sir Sam Hughes, (WWI Minister of the Militia,) purchased 2,500 acres of land around Moose Eagle Basshaunt and Glenn lakes and started building a summer home which he completed in 1919.
1921 – A few years following Hughes’ death, the family sold the property, which was then run as a hunting and fishing lodge.
Next, came the Proctor family who purchased the property and turned it into a summer resort.
And it begins …
1965 Enter – Bob Bishop Sr., a real estate agent who, upon learning that the province had chosen the site as potential for a ski hill, purchased it and created his and wife Noreen’s dream resort.
1979 – The Bishops ran the ski hill and resort for several years, and in 1979 had it divided from the hill and sold to Jim and Liz Orr. (In 2013, they sold the inn to Ryan Cole).
Legacy – Sir Sam’s Ski and Ride is the second-oldest family-owned ski hill in Ontario — a legacy matched by the generations of families who have chosen to call Sir Sam’s home for winter and summer fun, and countless treasured memories. A (near) year-round recreational centre (as coined by the Bishops) for guests who enjoy skiing or snowboarding all winter long, then trading the timber for mountain bikes the rest of the year.

An exciting new chapter
Now, in its 56th year, after almost six decades of working with thousands of dedicated staff, the 2021/22 season begins at Sir Sam’s Ski and Ride with new owners at the helm – Doug Wilkinson and family. The Bishops will work closely with the Wilkinsons to ensure a smooth transition, and continued quality skiing and boarding experience. The new owners are planning to expand the ski hill’s offerings and activities in the off-season.
NEW: Rhubarb on the Hill
The Wilkinson family have an affiliation with Chef Christoph Carl and Terri-Matthews Carl, owner of the Rhubarb restaurant in Carnarvon. “They are going to share some of their staff at the new Rhubarb on the Hill, here in Sir Sam’s chalet,” Bishop said, “which is presently under major renovation. When they’re not open and we are, they’ll be sharing some staff working with one of their chef’s, on the menu, offering an exceptional dining experience starting in December.”

Memories are made of this
When asked about his fondest memories at Sir Sam’s, Bishop said: “As a kid skiing here. I was nine years old when it started … and when I was in my early teens, when we’d get snowfall and have to groom the hills. We didn’t have groomers in those days, so we just packed it down with snowmobiles. I remember on a Friday afternoon Dad would pick us up and bring us to the ski hill and we’d drive the snowmobiles to pack the snow down. That was a pretty fun thing for a kid to do.”
“We’ve made a lot of friends, and have developed lifelong friendships with the people we have met here. We’ve had a lot of apres ski parties, dinners and dances … and had a lot of fun with interesting people we’ve met through the years.” Bishop said.

Major Thanks
“We want to thank all of the customers who have supported us, all the local business people, tradespeople and thousands of employees who we worked with throughout our 56 years in business. In the early days my parents (Bob and Noreen Bishop), all the people they relied on to get the work done, whether it was cutting the trees off the trail, or renovating Sir Sam’s Inn. They had a six-week time period to re-plummet and insulate and re-wire it to get it open for Fall season business. It was only a three-season inn at that time. So, the support of the community, whether you were a customer or an employee or a tradesperson. Thanks for making it all happen, and we look forward to the Wilkinson family carrying on the family tradition to make it their tradition.”

Future Plans
“All of our family members are staying on for the winter. It’ll be determined after the winter who wants to stay on. I’m here for up to a maximum of a year. Our familiar smiling faces will be here, and they’ll have the new faces of Doug and his family,” Bishop said. “The new Food & Beverage manager, Kaela, skied here since she was nine years old. She has a lot of history here, then she went away and worked other places and got lots of experience, and now she’s back as Food and Beverage Manager.”
Bittersweet?
“It’s sweet,” Bishop said. “It’s just time to pass it on, and we’re happy about it.”