Sir Sam's Ski & Ride

Year-Round Adventure

Sir Sam’s Ski & Bike

What began as a local ski hill established by the Bishop family in 1965 has, in recent years, taken on new life under the stewardship of Doug Wilkinson and his family. The Wilkinsons purchased the business three years ago, with a strong desire to keep the local icon thriving while expanding its reach and offerings. As Doug recalls, “We wanted to invest in a series of different businesses… Sir Sam’s Ski & Ride being the first one. We love it up here. We’ve been cottaging here for 20 years and just wanted to be part of this community.”

Under the Wilkinson family’s guidance, Sir Sam’s has become more than just a ski hill; it has evolved into a year-round destination that not only attracts tourists but also contributes significantly to the local economy and culture of the Haliburton Highlands.

A Four-Season Destination

Though Sir Sam’s is best known for its winter sports, Doug and his team have worked tirelessly to develop it into a multi-season destination. One of their most significant additions has been the Eagle View Wedding and Event Centre, which brings a fresh dimension to the property during the summer and fall months. The centre has hosted weddings, corporate events, and even community gatherings, drawing people to the Highlands for more than just the ski slopes. “It’s a great facility, and we’ve modernized the top of the chalet to accommodate groups of up to 250,” says Doug.

In addition to the event centre, the property now boasts hiking and biking trails that attract adventure seekers throughout the warmer months. Doug is particularly excited about their latest addition: an observation tower at the top of the hill. “The tower offers the best view of Ontario, hands down. People can come up in the spring and fall to see the incredible colours,” he shares. With plans to launch what Doug calls the “colour season,” Sir Sam’s is poised to attract visitors year-round. This observation tower also opens up opportunities for small, intimate weddings or corporate gatherings at the top of the hill, offering a unique way to experience the stunning scenery of Eagle and Moose

Sir Sam’s lookout tower

Commitment to Sustainability

Doug and his family are not only focused on growth but also on sustainability. “It’s something we care deeply about,” Doug explains. His stepdaughter, Brittany, who is pursuing her master’s degree in sustainability, has been instrumental in helping Sir Sam’s implement greener practices. One of the key changes they’ve made is in the restaurant, where they’ve moved away from disposable paper and plastic products in favour of compostable materials and reusable trays. “We’re trying to make sure we’re reducing waste and doing our part to keep the Highlands clean and beautiful for future generations,” Doug notes.

The family’s approach to sustainability extends beyond the restaurant. They have introduced a robust recycling program to handle the significant waste generated by the thousands of visitors Sir Sam’s attracts each year. “We’re always looking for new ways to be more eco-friendly and leave a positive impact on the environment,” Doug says.

Investing in the Future of Sir Sam’s

The Wilkinson family is keenly aware of the importance of continuous investment to keep the business thriving. One area of focus has been expanding and modernizing the ski hill itself. “We’ve made a lot of improvements, like moving one of our tunnels over to the beginner hill to create a better learning area,” says Doug. With more adults taking up skiing for the first time, Doug sees this as a crucial step in making the sport accessible to all age groups.

Sir Sam’s has also recently expanded its race program, which has seen increased popularity. The business is even set to host a Snowboard Canada race this coming January, marking the first event of its kind in years. “That’s a big deal for us,” Doug says proudly. “It’s another way to bring new eyes to the hill and get more people excited about what we’re doing here.”

Heading to the Hill

A Community-Centered Business

At the heart of Sir Sam’s success is its deep connection to the local community. Doug is proud of the fact that the business employs up to 130 people during peak season, providing not just jobs but also valuable training and opportunities for growth. “We’re really trying to make Sir Sam’s a community-based business,” Doug explains. “The ski hill is a huge tourist draw, but those visitors also go into town—they support local restaurants, shops, gas stations, and accommodations. It’s great to see how we’re helping the entire community thrive.”

In keeping with their community-first approach, Doug and his team have fostered partnerships with several local businesses, including Abbey Gardens, Boshkung Brewing Co., and local butchers. “We try to use as much local as possible,” he says. This approach not only strengthens the local economy but also enhances the overall visitor experience by offering a true taste of the Highlands.

Honouring the Past

As Sir Sam’s Ski & Ride continues to grow, Doug remains mindful of the legacy left by the Bishop family. “The Bishops were so helpful to us during the transition, and they’re still involved,” he says, noting that members of the Bishop family continue to contribute their time and expertise. JD Bishop, for example, is helping prepare the cross-track for upcoming snowcross races. “It’s great to have their support as we carry on the legacy of Sir Sam’s,” Doug adds.

Looking ahead, Doug and his family are excited to continue building on Sir Sam’s success. Their goal is to ensure that the ski hill and event centre remain a vital part of the Haliburton Highlands for years to come. “It takes time, but we’re investing now so that the community can reap the benefits for years down the road,” Doug says. “Our goal is to make Sir Sam’s a place that future generations can enjoy, while continuing to contribute to the overall success of the Highlands.”