#1 | 399 yards | Par 4

The first hole is a Par 4, ranging from 399 yards from the back tees, to 365 yards from the ladies’ tees. This starting hole offers a wide landing area – the hole is a slight dogleg left, with trees down the left side and a big maple tree on the right. Just left of the maple is a good aiming point. The approach is open in front, but both sides of the green are guarded by bunkers, and there are trees behind the green, which slopes gently toward the front.

#3 | 417 yards | Par 4

Hole 3 is a longer, up hill, slight dogleg left Par 4, measuring 417 yards from the back tees, and 284 yards from the ladies’ tees. This is a hole where a good tee shot is paramount. Trees line the left side, and several are present on the right, as well. A tee shot to the right side of the fairway opens up the green, as the green is protected on the front left by a bunker that hides the left side of the green. There are also bunkers behind to the left, and short right of the green, and a severe slope to the right, as well. The green itself slopes toward the front, and features a steep slope from the back right to front – hitting the ball over this green or to the right can leave a very challenging “up and down.”

#5 | 402 yards | Par 4

The fifth tee is elevated, and overlooks a Par 4 of 402 yards from the back tees, and 301 yards from the front tees. This hole turns slightly to the left; the drive should be aimed just left of the big maple to the immediate right of the green. With a wide landing area it invites a big tee shot; however, there is a “out-of-bounds” left, and a drive hit too far right will run downhill towards the 4th fairway, bringing the large greenside maple into play and leaving a longer approach shot into the green. The green is flanked by bunkers and is not elevated in the front, encouraging a “bump and run” type approach, but with the largest elevation change from the front to back of the green on the entire course, this green also receives aggressive shots at the pin easily.

#7 | 444 yards | Par 4

The seventh hole, ranked the #1 handicap hole on the course, is a long 444 yard (from the back tees) Par 4, and a still-challenging 403 yard Par 5 (for super seniors and ladies). The hole doglegs sharply left, with trees and a creek on the left side, leading to a former beaver pond at the corner. The tee shot hit straight away into an uphill landing area leaves an approach of close to 200 yards, to a green almost fully guarded by a bunker in front. The right side front, however, is open – allowing well-aimed balls to be “chased” onto the green on that side, and the green has a large slope from right to left to funnel balls back toward the center of the green. The approach is also flanked on the left by a steep slope leading to the large lake, and missing the green left, at best, leaves a very challenging blind pitch shot up the hill to the green. The right side is guarded by a tree line the entire way to the green, and missing the green to the right leaves a tough downhill chip shot back toward the lake.

#9 | 216 yards | Par 3

Hole 9 is the longest Par 3 on the course, playing 216 yards from the back tees, and a challenging 137 yards from the ladies’. Three bunkers flank the green, which slopes back to front, with a ridge running down the center. The right front of the green is steeper than the remainder, and makes for an extremely fast putt when behind the pin on that side. The ladies’ tees are positioned to the right of the men’s, which allows the right front bunker to hide that side of the green from the front tees. While being a very pretty hole to look at, most would agree that this is the most challenging Par 3 on the course.

#11 | 200 yards | Par 3

Hole 11 is the first Par 3 on the back, and measures 200 yards from the back tees, and 151 from the front tees. This hole has been redesigned; a bunker (which used to dominate the front of the green) was removed, and the hole received a new tee box, as well. Still flanked by bunkers, this is a fairly shallow green (but wide), divided by a spine coming from the back middle of the green – therefore, distance control is a premium on this “sneaky tough” Par 3.

#13 | 422 yards | Par 4

The thirteenth hole is perhaps the most scenic on the course, and is considered by many to be the course’s “signature” hole. It’s a straight Par 4, measuring 422 yards from the back tees and 287 from the front. Don’t let the beauty of this hole break your concentration, though, as this hole has teeth! The left side of the hole is lined by trees all the way up to the green, and the fairway slopes from right to left. A drive hit up the right side is preferred, allowing the ball to chase back down the slope into the fairway. Behind the hole in the distance, beautiful Mt. Pleasant makes the perfect aiming point – a drive hit toward the peak of the mountain will generally funnel back into perfect position for the approach to the green.

#15 | 371 yards | Par 4

The fifteenth is a hole, which plays down into a valley and back up, bending gently to the left as it goes up the hill. The hole measures 371 yards from the back tees and 290 yards from the ladies’ tees; this short Par 4 can be played in several ways. The landing area is not huge, so playing with a long iron, hybrid or fairway wood is the safe route. Pulling out the driver requires an accurate tee shot, with the reward of a relatively short approach uphill into this green. The green is guarded by bunkers left and right – the left bunker acting to hide that side of the green. There is also a “false front” leading to the green, which is relatively flat with the exception of the left side of it, which runs away from the fairway to the left.

#17 | 317 yards | Par 4

A short par 4, the seventeenth hole only measures 317 yards from the back tees and 235 yards from the ladies’ tees, but before you grab your driver, remember that this unique hole is a sharp 90-degree dogleg left. Figure on a tee shot with a middle iron, ideally placed at the far side of the fairway. Upon reaching the corner, the reason for getting to the far side of the fairway becomes apparent, as a tall, sprawling oak tree (one that most members dream of feeding to their woodstoves) guards the left side of the fairway. A shot left short of the 150-yard post in the fairway, leaves this tree very much in play. The green, guarded by flanking bunkers, is the smallest on the course, and is elevated above the fairway by a sharp slope. Shots left short generally run back down the hill and leave a semi-blind pitch to this shallow green. The right side of this green has several rolling undulations, but the left side is fairly flat. Don’t let this hole’s size fool you – it can be plenty tough.

#2 | 381 yards | Par 4

The second hole is a dogleg right Par 4 of 381 yards (from the back tees) and 354 yards (from the ladies’ tees). This tee shot is guarded at the corner of the dogleg by trees and a fairway bunker. The “safe” tee shot would be straight away, aiming at the biggest maple behind the fairway, leaving an approach of about 150 yards to the green. Challenging the bunker allows for a much closer approach, but if the ball is not struck well, the bunker or the trees can make for a difficult time. The green is a bowl shape, with bunkers left front, right front and back left. The right side of the front of the green is dominated by a large slope from right to left, which will catch balls hit to the front of the green. The preferred shot is into the middle of the green, leaving an uphill putt in virtually any direction from that point.

#4 | 377 yards | Par 4

The fourth hole is a nearly straight “downhill and back up” Par 4 of 377 yards (from the back tees) and 338 yards (from the ladies’ tees). This is considered by many to be the toughest-driving hole on the front nine. Several large trees (grouped in the bottom of the slope to the right) force the tee shot away from that side, but two large maples and a tree line on the left leave small room for error to that side. Many play a fairway wood, hybrid, or long iron off the tee here, to stay short of the narrowing landing area, leaving an uphill approach to the green. The green is kidney-shaped and two-tiered, with the deeper section to the right, and a well-hidden narrow section tucked behind the large deep bunker that dominates that side of the green. There is also a greenside bunker on the right.

#6 | 178 yards | Par 3

Hole 6 is the first Par 3 on the front, playing downhill and measuring 178 yards from the back tees and 166 from the ladies’ tees. The tee is a huge crescent shape, allowing for a variety of angles into a green protected on both sides by bunkers. The green slopes gently from back to front and accepts shots easily; low shots hit over the hill from the front tees funnel toward the green, making it perhaps the easiest Par 3 green on the course for most skill levels to hit in regulation. For this reason, this hole likely ranks highest on the course for surrendering the most “first ever” pars (or even birdies), to beginners and juniors alike.

#8 | 567 yards | Par 5

The eighth hole (the longest hole at Winton) is a Par 5, measuring a long 567 yards from the back tees, and featuring a huge landing area reached by an over-water carry. The lake flanks the start of the hole on the left, with out-of-bounds to the right. The ladies’ tees are 415 yards from the green, and are positioned past the lake. The drive there, however, still has to contend with out-of-bounds right. The second shot is uphill, and playing to the right side of the fairway affords a flat lie and a better view of the green. The approach is played to a very well guarded green, featuring bunkers left and right, a false front, and maple trees flanking the approach, as well. The green itself, while relatively flat on the right side, has a fair amount of back-to-front slope on the left, making for a fast putt when behind the hole on that side.

#10 | 376 yards | Par 4

After a “dog and a drink” in the snack bar at the turn, a short Par 4 is a nice way to ease back into your round. The tenth is just that – playing just 376 yards (from the back tees) and 336 yards (from the ladies’), the hole is almost straight and slightly uphill. A straight drive is a plus on this hole, as the fairway is guarded by trees up both sides. The approach shot from the fairway leads to a green with bunkers on both sides, which slopes gently back-to-front with undulations in several places.

#12 | 475 yards | Par 4

Hole 12 is the longest Par 4 on the course, measuring 475 yards from the back tees. Playing as a Par 5 (from the super senior and ladies’ tees), the hole still plays 400 yards. A dogleg left, the tee shot is among the most challenging on the course. The left side slopes sharply to trees and woods, and a shot hit right leaves only a lay up from among several trees, due to the distance involved. From the back tees, this is easily the most challenging hole on the golf course – the long approach shot plays downhill to a rolling green flanked by bunkers.

#14 | 549 yards | Par 5

The fourteenth hole is a Par 5, measuring 549 yards from the back tees, and 411 yards from the ladies’ tees. A tough driving hole offering a blind “over the hill” tee shot. Fortunately, there is a tower behind the tee box that allows viewing of the fairway (at which time you can also check the location of the group in front, to avoid hitting into them). The left side is tree-lined, and several large white pines guard the right side, as well. A drive hit slightly left of the mansion (seen from the tee) is a safe line to take. Long hitters can challenge this hole with a ball hit down the left side, which opens up the hole for an attempt at getting home in two. Beware, though, as it must be an accurate shot. The next shot is where this hole gets tough…the second shot is into a fairway that narrows down from the 150 yard marker in, with trees left and right. Bite off as much as you dare as you position for your approach to the green, since this shot is literally “make or break” for this hole. The green itself has bunkers left and right, and is perched on the edge of a hill which slopes sharply down to the left. The green is not very elevated, and is relatively small for this course. The left side of the green is fairly flat, but the right side has a good amount of slope.

#16 | 184 yards | Par 3

The last Par 3 on the course, the sixteenth hole measures 184 yards from the back tees and 143 yards from the ladies’, playing over a small valley to a green, which is perched on the edge of the far side. The front of the green slopes sharply to the front and left, toward a hillside pocked by a deep bunker which leads down to trees on the left, while the front right bunker guards the right half of the green. To the back right a shallow sand trap sits, waiting for shots hit too far right.

#18 | 558 yards | Par 5

The finishing hole on the course, while not the longest on the card, certainly plays that way. A straight, 558 yards (from the back tees, 415 from the ladies’ tees), this hole’s tee shot is downhill into a landing area that slopes back uphill, with out-of-bounds left, and a couple of huge maples on the right… so a good tee shot is definitely important. The second shot is all uphill to a fairly wide landing area with trees lining the right side, leaving an approach into this crowned green which is flanked by bunkers. The green itself is divided by a crown, which runs from the back center of the green forward, so it is not uncommon to see a downhill birdie putt on this green if the approach is not carefully placed.