From August 2018 Golf Odyssey: Southern Ontario’s Headwaters Region

Golf season in Canada may not be long, but moderate temperatures make for idyllic summer and early fall getaways. On our most recent foray north of the border, we headed to Southern Ontario’s Headwaters region, located less than an hour northwest of Toronto. While it may not be as topographically or culturally intriguing as other Canadian destinations, it’s a fascinating mini mecca for connoisseurs of golf course architecture.

Back in the early 1990’s, the creators of thewildly popular board game Trivial Pursuit enlisted Michael Hurdzan to build the sculpted and strategic Devil’s Pulpit and the links-style Devil’s Paintbrush. Both are among the finest private courses in Canada. We’ll have a review of the thoroughly entertaining Devil’s Paintbrush, which can be played if your home pro arranges a reciprocal round, in an upcoming issue. In the public sphere, Toronto-based course architect Doug Carrick designed three starkly contrasting layouts at Osprey Valley Golf.  Nearby Hockley Valley Resort, which has its own sporty Thomas McBroom-designed eighteen, is an ideal home base from which to sample all the layouts in the Headwaters region.

Osprey Valley, a true hidden gem, is the primary story here. The argument can be made that with the exception of Cabot Links, no Canadian multi-course public facility offers better golf. All three Osprey Valley layouts are top-100 Canadian courses. When the Heathlands Course debuted 26 years ago, it’s dunes, hollows, and fescue grass created an instant sensation. When the sand-laden Hoot and the parkland-style Toot courses came on board in 2000 and 2001, they elevated Osprey Valley to cult status for in-theknow golfers. The facility offers unheard of bang for your buck. With the advantageous exchange rate, the play-all-day green fee of $180 CDN ($200 weekends) is a steal.

Osprey Valley doesn’t have accommodations, but twenty minutes away you will find the elegant, family-owned Hockley Valley Resort. Hockley Valley started as a ski resort, but now with its golf course, accompanying winery, very good dining, luxurious pampering spa, and indoor and outdoor swimming pools, it has everything you need for a short getaway.

Osprey Valley Golf and Hockley Valley Resort are both just 45 minutes from Toronto’s Pearson International Airport (YYZ) when there are no traffic snarls. J. C. Munro Hamilton International Airport (YHM) is about 75 minutes away, but you can make up some of the extra time because it is a much smaller and easier airport to navigate. We’ve even used Buffalo Niagara International Airport (BUF) because of lower airfares and car rental rates, though it is a 2.5-hour drive to the Headwaters region.  Just keep in mind the golf season, which typically begins in early May, is short. Osprey Valley Golf ’s three eighteens close this year on October 13.

Valley Golf’s original eighteen. Doug Carrick emulated the characteristics of links courses he had studied on expeditions to the British Isles and Ireland. Though there are trees around, they are largely out of play on this wind-battered layout. Fescuecovered mounds and dunes form the corridors of each hole, and cross bunkers and some low stone walls further enhance the links ambience. The ground game is very much in play here, as a conscious decision to minimize watering helps keep the fairways fast and firm. Players who use the fairway contouring and feeder slopes around the greens to their advantage tend to score best.

The wind hurts more than it helps on Heathlands. There’s no better example of this than the long, bunkerless 6th hole, where it takes two powerful strikes to reach the green in regulation. The layout spreads out on 165 acres, making it the most confined of the facility’s three eighteens and also the most walkable. While the fairways aren’t tight, the penal nature of the tall grass, which isn’t cut in season, scares many players away. If you spray the ball, be prepared to go through a couple of sleeves or more during the round.

Editor’s Note: After the Hoot and Toot came on board, the routing plan was altered, but this year Heathlands has gone back to the way Carrick originally intended it to be played.

Osprey Valley’s second and third eighteens were built together. In contrast to Heathlands, both feature wide fairways that allow you to swing away with abandon on the tee.  Hoot (Rating: B+) , Osprey Valley’s highest rated course, is the most fun to play. Part of the playing field was built on an old gravel quarry.  With naturalistic bunkers, a lake and waterfalls on the back nine, and more than 3,000 transplanted pine trees, it’s the resort’s most picturesque layout.

Carrick sought to mimic the look and strategy of Pine Valley and Pinehurst from tee to green. Sand covers about 15 percent of the playing field. There are no traditional bunkers (and no rakes, either) here, as all of the sand from the fairways to greens is in waste areas that permit you to ground your club. Hoot’s large greens are the most benign at Osprey Valley.

Water, in the form of three lakes, enters the fray on eight of Hoot’s tests, including the final three. The par-four 17th, which features an elaborate waterfall, is often called the signature hole, but the manmade water feature seems out of character with the rest of the course.

Toot (Rating: B)  is a traditional parkland-style layout. The course just hosted the inaugural Osprey Valley Open, the firstever Toronto-area tournament on the Mackenzie Tour—PGA Tour Canada. While trees line the fairways, the woods aren’t thick and the corridors are generous, lending a much more user-friendly aspect to the game. Traditional bunkers help provide definition to holes whose gapingly wide fairways are actually tough to miss from the tee.

Like the other Osprey Valley playing fields, Toot spools over mostly flat ground, though it is spread out and not really conducive to walking. Carrick ramps up the strategy around the elevated greens. Toot’s putting surfaces are the fastest and trickiest at the complex. While they don’t have a lot of undulation, they tilt from back to front and generally roll at about 11 on the Stimpmeter.

Osprey Valley’s practice facilities include a driving range and putting green. Though the clubhouse is somewhat spacious, it’s not elaborate. The food offerings are primarily snack-bar fare.

Given Canadians’ passion for golf, its amazes us that Osprey Valley is still an undiscovered treasure. With the exception of group outings, the tee sheets are seldom crowded. This year a new annual membership program was implemented, resulting in a spike in play. Nonetheless, you can usually call and get a tee time around the time when you wish to play.

The fast pace of play makes playing multiple rounds an especially enjoyable proposition at Osprey Valley. The staff in the golf shop does an excellent job of sending groups off so other groups don’t bog them down. It’s quite common for players to complete rounds on all three courses with light to spare in June, July, and early August.

Editor’s Note : Youths sixteen and under play for free when accompanied by a paying adult. Seventeen and eighteen-yearolds are charged 50 percent when accompanied by a paying adult.

Hockley Valley Golf Course (Rating: B-) , located right behind the resort hotel and adjacent to the resort winery, is a picturesque but quirky Thomas McBroom design from 1990. While the layout is not in the same league as Osprey Valley, it makes for a convenient warm-up or getaway round if you are staying in-house. Whereas some designers doubted whether an eighteen-hole layout could be built on this confined, hilly site that serves as a ski resort in winter, McBroom created a tight, short layout with small greens. Aside from the first and last holes that hug the valley floor, the terrain is all up and down. Most of the front nine plays uphill. From the green on the 9th hole, a short drivable par four, you can look out over the entire valley. In fall, the colors are gorgeous.

The hilly nature of the playing field leads inevitably to a number of blind shots and awkward lies and stances. Several holes are exceptionally tight, and if you miss the fairway your ball will wind up in very thick rough. One of the quirkiest aspects of the course is that all the bunkers feature ornery grass and clover rather than sand. Back in 1990, the course opened before the bunker sand was delivered. To minimize cost and make for easier maintenance, the resort never bothered with the sand. Alas, all the tall grass often slows the pace of play to between 4.5 and five hours on this scenic, sporty track.


Hockley Valley Resort (Rating: A) has been the pride and joy of the Adamo family ever since they acquired the property in 1985. They’re built it into a four-season retreat that’s a very popular weekend getaway for well-heeled Torontonians. Though we were eager to take the golf course for a test run, more guests are drawn to the luxurious spa, the sophisticated dining, and the indoor and outdoor pools. The staff provides a warm welcome and personal service. Be advised you may need to book early to get the room and dates you desire. Finally, check for a resort package that can save you substantially over à la carte pricing.

Though the boutique-style resort has been through its share of additions and renovations, an air of romance and bucolic serenity wafts through this rural retreat. The contemporary-styled rooms and suites, many of which feature balconies, look out on the pond, the golf course, or the valley. For heightened elegance, the bi-level Regal/Vice Regal Suites feature a spiral staircase that leads up to a king bed, Jacuzzi tub, and spacious bathroom. The lower level has a fireplace and a generous living area. These suites also feature double balconies with sweeping valley views.


Hockley Valley Resort (Dining Rating: B+) has three dining options, all of which share the same kitchen. Every morning, an extensive breakfast buffet is set up in  Eighty-Five. The stylish Babbo Wine Bar & Patio, which comprises the lobby bar and lounge and the poolside patio, serves food from 11 a.m. until the kitchen closes. The menu lists a few small-bite dishes as well as a limited number of more substantial salads and entrées. We ordered steak frites. While the dish was very good, it hardly seemed like a “large plate” option when just two tiny beef tenderloin medallions came with the frites.

Despite its name,  Cabin, Hockley’s Valley’s dinner restaurant, is more modern than rustic.  The ambience is enriched by an elaborate display of wine bottles, a contemporary fireplace, a 16-foot steel and glass chandelier, the chef ’s counter, and the exposed kitchen. While the menu isn’t extensive, the cooking is creative and the plates are nicely presented.  We recommend the Arctic char and the pan-roasted chicken. Many of the seasonal vegetables and herb come from the resort’s organic farm.


Hockley Valley’s full-service spa occupies much of the third floor of the hotel.  The facility includes very nice co-ed and women’s relaxation lounges with fireplaces, though it lacks a sauna and whirlpool. Be sure to arrange your services prior to your arrival.  The resort has an indoor pool and a heated outdoor pool.  A small workout room, located near the indoor pool, features a few cardio machines and some dumbbells.

If you’re looking for additional outdoor activities, Island Lake in nearby Orangeville is a nice spot for hiking, biking, and running.  Canoes, kayaks, and paddleboards may also be rented there.

Two years ago, Hockley Valley Resort opened a full-service winery just a kilometer up the road from the hotel. The Adamo Estate Winery’s most popular varietals are a dry Riesling and a Merlot. Tours, tastings, and small plate bites are offered.

Tasting A Fabulous Golf Foursome

Great Canadian golf? Where do you find it? The answer may surprise you.

Few areas of Canada can boast as many quality golf courses as what you can find in the York Durham Headwaters – Ontario’s Central Counties. The land lends itself to the game, with rolling hills, dense stands of forest, and panoramas that allow you to be fully immersed in nature.

On the eastern side of this region, which touches the edges of Toronto and stretches to more rural landscapes to the north, are a foursome of facilities that welcome golfers to their well-manicured and intriguing grounds. Royal Ashburn Golf Club, The Briars Golf Club, Wooden Sticks Golf Club, and Angus Glen Golf Club each stand on their own as desirable places to play, but together create a golf collective that will leave you with nothing but admiration.

It starts with the Royal Ashburn Golf Club in Whitby, which has been hosting golfers for more than 55 years. Over that time constant improvements have been seen, enough to have allowed it to be the host of the qualifying school for the Canadian Tour for many years.

At 7100 yards Royal Ashburn can be a stern test for accomplished players but any golfer can enjoy the mature layout with multiple tee decks, including those as playable as 4,783 yards. 

Add in an extensive practice area, and comfortable clubhouse and you’ll soon see why this course remains a go-to course in the region.

Ever wanted to play some of the best layouts in the world? You have that opportunity in Uxbridge where tribute holes and brilliant original designs mark the property at the Wooden Sticks Golf Club.

Not only will you see glimpses of the world’s most notable holes, but you’ll experience what the club has been known for from their very beginning – world-class service. Delicious meals, extensive practice facilities, and on-site accommodations in well-appointed cabins make Wooden Sticks stand out in a province full of great properties.

If you want a multiple course option in one location, Markham, Ontario’s Angus Glen Golf Club is your spot in the eastern half of the York Durham Headwaters. Unlike many 36-hole facilities where one course shines over the other, the North and South layouts have both been strong enough to host the PGA TOUR’s RBC Canadian Open. At the same time each has a distinct architectural flavour. Playing one will only lead you to want to tee it up again on the other.

Moving further away from the Greater Toronto Area, The Briars Golf Club is a walk back in time to a golden era of golf club design. The original nine holes were crafted by the hand of Stanley Thompson in 1922 with the delicate addition of another nine by the equally respected Robbie Robinson in 1972.

With the full feel of a private club and a setting on the southern shores of Lake Simcoe, The Briars Golf Club is a true Canadian retreat.

Royal Ashburn, Wooden Sticks, Angus Glen, and The Briars; just four more reasons why you should be teeing it up in the York Durham Headwaters – Ontario’s Central Counties.

Golf in The Hills of The York Durham Headwaters

If you have played golf for any time you will have experienced courses that fall on the bland side. You know them – flat, unimaginative designs that serve the purpose of playing the game but do nothing to pique your senses and foster your love of the sport. That is the kind of golf we all look for and in the western part of York Durham Headwaters, which skirts the top edge of the Greater Toronto Area, there is plenty of this to be found. In fact, they almost have an embarrassment of riches when it comes to golf.

Want all the golf you can handle in 6500 yards? The well-established Caledon Country Club in the town of the same name is a fabulous introduction to this area of Ontario. It all kicks off with a risk-reward 240-yard par four where an eagle is a possibility and continues all the way through eighteen holes that asks for strategic precision from the golfer. The reward for all is premium conditioning in a setting where architect Rene Muylaert made the most of the Caledon Hills landscape.

Twenty-seven holes are offered at Caledon, a club where its former name meant “Land of Pines” – a great indication of what you will find on their sprawling property. One that is easy to enjoy.

With similar D.N.A (it is also 27 holes and designed by Rene Muylaert) not far from Caledon Country Club you will find the Glen Eagle Golf Club near Bolton. Established in 1962 and situated in the Albion Hills through the years this course has been a familiar stopover for some of Canada’s Hall of Fame golfers.

Whether you choose to play the Red, Blue, or Yellow course (we suggest all three) you’ll be sure to enjoy the rolling topography, distinctive bunkering, and mature setting. It is particularly spectacular in the Fall when the golden hues of the leaves add even more beauty. The club also specializes in celebrations but whether you are a single golfer or a wedding party of 250, they’ll ensure you enjoy your stopover.

Wandering to nearby Tottenham, one the youngest (1995) courses in the region, Woodington Lake Golf Club, presents another 36 holes of spectacular golf. Near to Newmarket and Orangeville, the heart of this club is a sprawling 32,000 clubhouse perfect for any occasion. That is, unless you are an avid golfer. In that case the two eighteen-hole layouts will demand your immediate attention.

The original Legend Course winds its way around Woodington Lake, making full use of it’s beauty. Carved out of a pine forest, the holes enjoy singular settings among the 200 acres they cover.

Those preferring a more “open” experience will be attracted to the newer Legacy Course. That said, the “open” label does not mean easy. Large, fast greens will test your short game while an abundance of other features will keep your attention all day long.

If a full resort experience is your preference, then the Hockley Valley Resort in Mono should be part of your golf plan in this region. Boasting a full resort with dining facilities, a spa, and even a winery (along with skiing and snowboarding), the Hockley Valley Resort became a true four-season resort in 1980 with the opening of their Thomas McBroom-designed golf course.

At less than 6400 yards, their golf course is suitable for all levels of players. Lush bentgrass tees, fairways, and greens carpet the course which is accented by long fescue grass as it winds its way through the rippling terrain. There is no shortage of elevation changes, providing some exceptional views across an untouched natural landscape.

Just when you thought you had your fill of golf, there are still 54 holes left to discover in this region, all found at Osprey Valley Golf. Your first look may leave you shaking your head in disbelief as on a property of staggering size there exists three very distinct golf courses, all built to world-class specifications.

You can have your choice of styles at Osprey Valley, from the parkland Toot course, to the waste bunker ridden Hoot, or a linksy affair at Heathland. The hardest part is deciding which to play but stick around for some extra time and you can pack in all three. If you do you’ll be sure to run into many happy golfers (and maybe even some famous ones) who continue to tout this facility as one of the best that the pubic can access in the entire country.

It’s just another testament to this region, the quality of golf being offered, and why you should be booking your next golf vacation in the York Durham Headwaters-Ontario’s Central Counties.