50th Anniversary

12 Days Of Squire John's - 50th Anniversary Edition


The Staff

Former Employee James O’Keefe “We are not in the ski business serving people, we are in the people business serving skiing”. Happy Holidays from all the staff at Squire John's!  

The Staff


The Store

The store has undergone many renovations since the first square bricks and mortar structure was built. In total there have been three structural renovations, one that created more space on the back of the square footprint, the other was a right wing rectangle shaped addition (boot room) and the final was the emporium built off to the left side of the boot room. John Will had some fun with the property in the early years. He dug a pond in the back, carved out dirt bike tracks and put up a basketball court. Christie Will Wolf remembers that all the neighbour kids loved to visit because their place was “the place” for kids to have fun and hang out.

Recently the store has undergone some interior renovations. There has been new carpeting laid throughout the main floor and stairs, refinishing of the boot fit bench, a new custom cash desk with glass top and the offices also had new flooring laid.

The Store


The Tent Sale

Helen Kimble started the tent sale as a way of clearing out previous seasons stock that had not sold. The yellow & white tent featured in the photo was one of the first tent sales ever held. Since Helen’s years the tent sale has grown, not only in the space it takes up in the parking lot but also in the volume of goods sold throughout the weekend. It is officially the largest tent sale of it’s kind in Ontairo! To say it has reached legendary status as a “must attend local event” would be an understatement. Line-ups begin early on Friday morning and the tent is buzzing with activity all weekend long. Partners also attend the event, along with local charities like the Golf Ball Ladies who are raising funds to support My Friend’s House in Collingwood.

The sale also provides an amazing opportunity to catch up with winter friends in the summer. Staff, customers and dealers all re-connect throughout the weekend and dream of the day when the white stuff starts falling from the sky and they will be back on snow skiing and snowboarding!

Tent Sale


Bike Events 

Helen Kimble created several mountain bike events that took place at Blue Mountain. She also supported local cyclists as they competed in Ontario Mountain Bike events throughout the Province. When Shane took over the bike side of the business in the summer of 1998 he sponsored The Fly Gurlz Women’s MTB Team, who went on to become the largest organization of it’s kind in Canada! This legacy of support continues with the store sponsoring local Athletes Stephanie Martinek and Erik Downing as they compete provincially on their bikes. For many years Squire John’s also hosted kids learn to mountain bike camps that were a huge success and well attended. Currently during the spring and summer Rocky Mountain Bicycles, Pivot Cycles and Specialized Bikes host Demo Days for the store at 3 Stage near Collingwood. Squire John’s also sponsors a ride night with CORC (Collingwood Offroad Cycling).

Bike Events


Ski Demo Tour

The Squire John’s ski demo program began during Helen’s tenure at the Men’s and Ladies ski days which took place at all the private clubs across the Escarpment. She thought it was a great way for skiers to try out new equipment before they purchased. They were a huge success and soon expanded to alternating Saturdays and Sundays at the 6 private clubs. Throughout the winter months there are 3 types of Demo Tours on the road. The first is the Super Ski and Snowboard Tour which takes place the week following Christmas Day. It includes participation from many of the ski and snowboard brands sold at the store, along with partners like CMH Heli-Skiing and Summer Adventures and Big White Ski Resort. The second is a Super Ski Demo tour which includes participation from many of the ski brands that are sold at the store. The third Demo Tour is hosted by the Squire John’s in-house Demo Team and includes a great selection of skis from many of the manufacturers that are sold in the store.

The Demo Tour is backed up by years of expert knowledge. It provides an opportunity to test out the latest technology and try before you buy. Visit HERE to see the full 2020 Demo Tour Schedule.

Demo Tour


Shane Kilfoyle – Partner/Co-Owner

Shane starting skiing in grade 9 after moving to Collingwood from the city.  In the fall of 1988 he visited Squire John’s to have a set of foot beds made.  This was the day he met John Murray, John Belk and James O’Keefe who were all working as boot fitters.  After being ridiculed for his boots being too big, this meeting struck up a friendship that has lasted over 31 years. In the summer of 1989 Shane joined John Murray to work for his landscape business GBLC and spent his first winter working at the store in the fall/winter of 89/90. Shane continued to work with John in the summer and at Squire’s in the winter while he attended Wilfrid Laurier University. In the Spring of 1997 Shane left Collingwood to move to Toronto to be closer to his wife, who was working in the city full-time. That summer, while visiting with Helen in Collingwood, Helen told Shane that she was ready to move on and it was time for someone else to take over the business.  Shane called John immediately and thus began the partnership to take over Squire John’s.

Shane is proud that after 22 years his partnership with Mark and John is still going strong. Back in the day, staffer James O’Keefe said “We are not in the ski business serving people, we are in the people business serving skiing”. This captures perfectly how Shane feels about maintaining a family oriented and people-centric environment in the business. “We want to look after our people, develop long term relationships, stay relevant and grow steadily in an industry that is always evolving”.

Shane Kilfoyle


Mark Andersen – Partner/Co-Owner

Mark started skiing when he was 4 years old at Craigleith Ski Club. He met John Murray at the age of 16 while night skiing at Blue Mountain. This forged the start of a friendship that would last a lifetime. Mark remembers shopping at the store in his late 20’s and early 30’s. At that time, he was working in Toronto in the IT sector, coming up on weekends to spend time on the ski hills. In the summer of 1997 Shane and John called their friend Mark to see if he might be interested in buying into the shop and becoming partners. Mark jumped at the chance and in the fall of 1997 he moved up to Thornbury to begin working full-time at the store.

Mark is proud of Squire’s customer service and great employees, “We empower our staff to make decisions and the goal is to create a fun and hardworking environment.” There are staff members like Al Phillips who have been with the store for close to 20 years. This kind of retention is rare these days and is a testimony to the legacy that was carved out originally by John, Peggy and Helen.

People will sometimes spend hours in the shop which creates and fosters something beyond the typical retailer and customer relationship. “We have great customers who return, year after year, we want them to feel comfortable and cared for when they shop in the store.”

Mark Andersen


John Murray – Partner/Co-Owner

John started skiing at the age of 14 as part of his High School ski program. When he was 15 he got a job as a liftie at Blue Mountain Resorts where he met Mark Andersen night skiing.

John began working at Squire John’s in 1982. He worked winters at the shop under Helen’s leadership and he spent summers  running his own landscape company called “Georgian Bay Lawn Care.” Initially John worked part-time at Osler and Craigleith, and then he graduated to manager of the Alpine Pro Shop for two years. It was at this point that John moved over to the main store and put his boot fitting skills into action. John also took on the role of managing the private club shops.

John took a season off from his job at Squires to travel to St. Moritz, Switzerland. Living off yogurt and baguette and barely any money to his name, he found employment at a local ski shop. It was this experience that solidified and expanded his love for skiing and retail.

John recalls that Helen was an incredible mentor who led by example and created a welcoming atmosphere for all staff who worked for the Squires team. In 1997 Helen decided that the time had come to pass the Squire John’s torch on to new owners. Shane recalls the summer of 1997 when Helen approached him about the possibility of buying the shop. He called John from the very office they work in today to see if he would be interested in developing a partnership!

John is most proud of the long-term staff relationships that have developed over the years. John ensures that all staff feel part of the Squire’s family. John can be credited with organizing the first Mill Lake staff summer retreat in 2006. 13 years later, this event continues to be an annual tradition that staff eagerly look forward to.  

The three partners have built a solid foundation for their employees based on loyalty, support and caring for each other.

John Murray


John Band – Co-Owner

The early story of Squire John’s wouldn’t be complete without mentioning John Band. He was a special person and as Helen put it “all around great guy”.

When Helen took over the business, she wanted to put an extension on the store and John invested in the company to help Helen complete the renovation. At the time John was a customer of the store and lived and breathed Squire John’s. He was a passionate skier, outerwear aficionado and Helen recalls “putting him in the most outlandish outerwear that was on the store floor and he always pulled it off, he was a boisterous & special Ambassador for the store”.

The legacy of the Squire John's Ambassador continues to this day with many athletes representing the store on the front lines!

John Band


Helen Kimble – Owner (1986-1997)

Helen started working at the store in 1973 and took over ownership in 1986 when John Will passed away. In the late 70’s John and Helen had become partners in the business as well as partners in life.

When Helen acquired the store all of the day to day business operations became her responsibility. She recalls “Being a woman in what was a male dominated business, I had to gain respect from the dealers, reps, staff and keep the established relationships at the Private Clubs running smoothly through the transition”.

She says her management style was tough but fair “I always treated the staff well, had their backs and provided opportunities for growth and this fostered loyalty within the company.”  Helen also brought plenty of fun to the workplace. She introduced fashion shows, PK nights, BBQ’s and parties where staff could let off some steam and enjoy the comradery and friendship that being a part of the Squire John’s family provided.

Helen greatest achievement was the way in which she nurtured a family like atmosphere for the staff throughout all the chaos that took place while running retails stores. This legacy of loyalty and caring for staff members, suppliers and customers has been passed down through the current owners Mark, Shane and John. This was a natural progession as both John and Shane worked for Helen at the store while she was the owner. They learned from the best!

Helen Kimble Day 3


Peggy Cahill Will – Founder

Peggy and John met while attending University. Peggy was just short of graduating to become a dental hygienist when she left school to pursue the idea of opening a ski shop with her soon to be husband John Will. The couple married in 1970 and soon after that had 2 daughters, Kate and Christie.

Christie Will Wolf remembers her Mom as being a wholesome soul. She was smart, super stylish and had a great eye for curating and sourcing ski soft good brands.

Christie remembers living above the shop and having her Mom chase both she and her sister back up the stairs to the apartment while the store was open! She recalls those years as being fun and that Peggy helped to lay the foundation for the fashion side of the store. Her legacy for curating and sourcing a wide variety of unique soft goods is still happening today through all the talented buyers at the store.

Peggy Cahill Will


John Will – Founder

Squire John’s was established in 1969 by John Will and Peggy Cahill Will. The dream was to move to Collingwood from Toronto and open-up a ski shop that would service skiers in the area. John thought the region needed a ski shop as there was no other established full service store in the Collingwood area at that time.

When John and Peggy purchased the land, the road along Highway 26 in Craigleith was pretty much in the middle of nowhere which reflected the affordable price tag! Soon plans were made to build a shop with a basement for tech, a main floor for sales and family accommodation on the second floor.

A great example of John’s enthusiasm was recently shared by former second owner Helen Kimble. Before John moved to Collingwood he was working at a ski shop in Port Credit and discovered a new “ski press” that could repair skis using the latest technology available. John bought the ski press before he had the store, his philosophy being “If I build it they will come”. John Will was a Dreamer in the truest sense of the word.  

John hired builder John Squire to help him build the shop from the ground up. When the time came to name the store John decided to reverse his friend’s name and call it Squire John. When looking at the earliest examples of store photographs there was no ‘s’ at the end of John’s. This was added later and became what we now know as the store name Squire John’s. Staff, customers and dealers soon began referring to John Will as “The Squire” and this became his nickname throughout the ski community in Collingwood.

John established himself as one the best ski technicians in the area. He serviced some of Canadas top skier racers, as well as all the families skiing and competing across the escarpment. The store established itself as a must stop destination on the way to the ski hill on weekends and holidays!

It was also during John’s time when the store began setting up satellite shops at the private ski hills throughout the region. The first club to give Squire John some shop space was Osler Bluff Ski Club. Then in the following years the store set up Satellite Shops in all of the Private Ski Clubs with the last acquisition being the purchase of Slalom Gate Ski Shop at the Georgian Peaks Ski Club in 2015. 

12 Days of Squire John's