Matthew and Ashley Fair Begin a New Chapter at Crestwood Golf Club

COLLEEN GREEN The Standard

For Matthew and Ashley Fair, taking ownership of Crestwood Golf Club is much more than a business venture, it is the fulfillment of a lifelong dream rooted in family memories, community spirit, and a deep love of the game.

The couple officially purchased the golf course earlier this year after the sale closed on April 1st, and they are already hard at work carefully modernizing the facility while preserving the welcoming atmosphere which has made Crestwood a favourite among local golfers for generations.

“I truly love this place,” said Matthew Fair. “I’ve golfed here for 30 years. I started here as a young boy and had my first golf lesson here. I learned to golf with my father here, so it holds a very special place in my heart.”

That personal connection made the opportunity impossible to pass up.

“Ever since I was little, I decided I would own this place,” he said. “So when the opportunity came along, I jumped at it.”

Originally established as a private course in the early 1940s on what was once a cattle farm, Crestwood officially opened to the public in 1969. Since then, the course has built a loyal following throughout Port Perry, Sunderland, and the surrounding communities.

Matthew and Ashley are quick to credit longtime owner Bruce Grant and his family for creating the strong foundation they are now building upon.

“Bruce built a really special community here,” Ashley Fair said. “There’s a really good soul to this place, and everyone wants to see that continue.”

Rather than rushing major changes, the Fairs say their first season is focused on thoughtful improvements to enhance the golfer experience while maintaining the relaxed and welcoming atmosphere members and visitors have come to love.

Inside the clubhouse, renovations have included fresh paint, upgraded lighting, new televisions, and a redesigned pro shop area. Outside, the course is receiving ongoing improvements to fairways, bunkers, greens, and landscaping.

One of the club’s newest additions is an autonomous rough mower, one of the first of its kind at a local course, which allows staff to spend more time refining greens, tee blocks, and bunkers.

“It frees up our maintenance team to focus on the finer details which really elevate the course,” Matthew explained.

Although Crestwood is technically a nine-hole course, it offers what Matthew describes as a “hybrid 18-hole experience,” with multiple alternate fairways and layouts which provide variety and challenge for golfers of all skill levels.

“It’s approachable for beginners, seniors, and families, but it can still challenge experienced golfers,” he said.

Community continues to be at the heart of the club’s identity. Crestwood hosts numerous leagues and social events throughout the week, including the Canterbury League, Legion League, Men’s Night, Ladies groups, Senior tours, and beginner-friendly golf clinics.

The Canterbury League alone has approximately 140 registered members, with up to 72 players participating weekly.

The Fairs are also passionate about introducing younger generations to the sport. Crestwood’s youth camps are already fully booked for the summer, and the course continues to host junior tournaments, school practice rounds, and free Friday golf for children playing alongside adults all summer long.

“That’s one of the things I’m most excited about,” Matthew said. “Seeing the junior programs growing again is incredible.”

Beyond golf, the clubhouse has become a lively social destination featuring a fully licensed restaurant and patio serving classic pub fare, league-night dinners, steak nights, socials, and popular date-night events.

The course has even introduced its own custom beer, the Crestwood Lager, affectionately known as the “Bag Beer.”

Looking ahead, the Fairs envision expanded event spaces, wedding ceremony locations, improved practice facilities, and continued course enhancements over the next several years.

“We want everyone to feel welcome here,” Ashley said. “From people trying golf for the very first time to golfers who’ve been coming here for decades.”

Affordable memberships, accessible green fees, club rentals, and a strong focus on community continue to make Crestwood one of the region’s most approachable golf destinations.

A formal grand reopening celebration is expected later this summer, with more details to be announced soon.

Additionally, the Fairs are incredibly fortunate that every existing staff member not only chose to stay on through this transition, but did so with genuine excitement to be part of this new journey. That same enthusiasm and passion was immediately shared by the newest additions to the team. This speaks volumes about the culture and spirit that makes Crestwood such a special place.

A heartfelt thank you goes out to all of the past and present stewards of Crestwood from previous owners, to current and future members, guests, and patrons; whose passion, support, and dedication continue to make the club a truly special place for everyone who walks through its doors.

A formal grand reopening celebration is expected later this summer, with more details to be announced soon.