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A golf fanatic picks the 18 best holes to play on New England courses

Plus, the three toughest holes; all guaranteed to challenge even the best golfers.

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As a golf-obsessed teenager, I’d sometimes spend rainy days with a large sheet of paper designing a golf course by hand with colored pencils. I’d doodle dogleg par-4 holes, reachable par-5s, short and long par-3s, adding treacherous water hazards, deep bunkers, narrow fairways, and occasionally a double green — all connected in a way that made sense.

Now, as a golf-obsessed adult who writes about the game, I continue to dream of creating that perfect course. Having lived in — and played golf throughout — New England for nearly 20 years, I’m surrounded by a number of perfect golf holes, so I thought it would be a fun challenge to come up with my personal list of the best18.


The first step was establishing ground rules: The holes would come from private clubs and public courses, I’d have four par-3s, four par-5s, and 10 par-4s for a traditional par of 72, and the list would represent all six New England states. To make the cut, a hole must be memorable, visually appealing, and difficult on some level, and each one ideally has a bit of history behind it.

Using the score card yardage from the white tees, my “course” measures 6,467 yards and includes holes from New Haven, Connecticut, to Jay, Vermont, and many points in between.

How does your dream course compare?

1. Whitinsville Golf Club — Number 9 — Par 4, 446 yards

Peter and Maria Hoey

> Whitinsville, Massachusetts; Private

Few closing holes are as stout as this one, and since Whitinsville is a nine-hole course, you get two cracks at it during an 18-hole round. This hole is usually played into a prevailing wind, with a hazard running down the right side of a steep and undulating fairway. Because the green is elevated, slopes down in front, and has a back portion that slopes away, approach shots must be precise. There might not be a better finishing hole in New England.


2. TPC River Highlands — Number 15 — Par 4, 247 yards

Peter and Maria Hoey

> Cromwell, Connecticut; Private

Short par-4 holes are always a welcome change from the steady diet of long, challenging two-shotters many courses offer. TPC River Highlands hosts the Travelers Championship every year, so when the best players on the PGA Tour reach this tee box, they’re all dreaming of driving the green and making the putt for an eagle 2. But with water left, woods and bunkers right, and a two-tiered green with run-off on all sides, walking off with a 6 isn’t out of the question.

3. Newport National Golf Club — Number 14 — Par 5, 487 yards

Peter and Maria Hoey

> Middletown, Rhode Island; Public

It may not be as unforgettable as the 13th hole at North Berwick in Scotland, where a rocky barrier is positioned right in front of a green, but how many courses make you hit over a stone wall? The 14th at Newport National does — its distinctive barrier lies between the tee box and the start of the fairway. The hole gently moves right as it nears the green, which is protected by two bunkers in front and tall fescue grass if a miss goes left, long, or right.

4. Essex County Club — Number 11 — Par 3, 160 yards

Peter and Maria Hoey

> Manchester-by-the-Sea, Massachusetts; Private

Created by famed course designer Donald Ross, this gem on the North Shore boasts many unforgettable holes, none better than the uphill 11th. Deep bunkers guard both sides of the green and create an intimidating look from the tee, with only a fraction of the putting surface visible. “Most memorable par-3 holes play downhill, set to some stunning backdrop. The 11th at Essex County Club plays uphill over and against nondescript land,” says Jack M. Davis, the club’s head golf professional. “The architecture is so well done that players of all handicaps have a chance to make a 3 yet fear a 5.”


5. Southers Marsh Golf Club — Number 4 — Par 4, 353 yards

Peter and Maria Hoey

> Plymouth, Massachusetts; Public

There aren’t many courses in the region that offer a setting or an experience quite like Southers Marsh, a par-61 with 11 par-3 holes that winds its way through a working cranberry bog. The fourth hole brings a bog into play twice: You’ll need to carry one off the tee, then another on the approach shot. The smell and the scenery are distracting; best be focused on this hole, though — or else.

6. Wannamoisett Country Club — Number 3 — Par 3, 127 yards

Peter and Maria Hoey

> Rumford, Rhode Island; Private

Seems simple: With a short iron, from a manageable distance, find the green with your tee shot, then take two putts and leave with a par. Ah, but the beauty of Wannamoisett’s signature hole is in the details. The green is raised but small. A large bunker comes off the hill to the left and wraps around the front. Everything slopes right, where a small creek lies in wait. “It will give players of all skill levels fits,” says Wannamoisett’s head professional, Ed Clark. “But when it finally allows for a birdie, it will have been worth all of the drama.”

7. Portsmouth Country Club — Number 12 — Par 4, 452 yards

Peter and Maria Hoey

> Greenland, New Hampshire; Public

My favorite hole on this Robert Trent Jones Sr.-designed course is the 12th, a long, straight par 4 that heads toward Great Bay, the green finishing steps away from the water. This hole’s beauty is in its simplicity: No fairway bunkers, a lone tree left of the fairway, a single bunker short and left of the green. Wind can be a factor. Enjoy the view of the surrounding bay while you’re there; you won’t be disappointed.


8. Cape Arundel Golf Club — Number 10 — Par 4, 345 yards

Peter and Maria Hoey

> Kennebunkport, Maine; SemiPrivate

George H. W. Bush, the 1947 club champion, enjoyed playing here for several reasons. He liked the challenge, the views, and a quick pace. He also liked the dogleg right 10th hole. “The two-tiered narrow green is among the trickiest and greatest at Cape Arundel,” says longtime member Pierce O’Neil. “Approach shots that land on the left, right, or back edges will roll off into trouble and leave the player facing bogey or worse. The green sits at the highest point on the property, with a 360-degree vista down the Kennebunk River and over the entire links.”

9. Ekwanok Country Club — Number 7 — Par 5, 568 yards

Peter and Maria Hoey

> Manchester, Vermont; Private

Construction began on this course in 1899, and the seventh hole, like the others, has been largely unchanged since the legendary Walter Travis designed it. Two large mounds bisect the fairway 300 yards from the tee, creating a blind second shot over the hill. The green is small and guarded by bunkers, as you’d expect on a par 5.

10. George Wright Golf Course — Number 9 — Par 4, 440 yards

Peter and Maria Hoey

> Hyde Park, Massachusetts; Public

The first of two back-to-back round-wrecking par-4 holes, the ninth at George Wright requires a pair of A+ swings to reach the green. The drive is semi-blind and leaves a downhill shot from a side-hill lie to a tough green to hit. On that approach shot, if the ball goes long, left or right, the player is faced with a difficult up and down. Par here is well earned.


11. Mount Washington Resort Golf Club/Mount Pleasant Course — Number 6 — Par 4, 415 yards

Peter and Maria Hoey

> Bretton Woods, New Hampshire; Public

It might not receive the attention or adulation bestowed on its somewhat younger sibling, the Mount Washington Course, but the resort’s Mount Pleasant Course is a fun, underrated nine-holer that dates to 1895. For my money, the best hole on the property is the sixth, a soft dogleg left with the Ammonoosuc River guarding the right side. It’s OK to let your eye wander while playing here; that way you won’t miss the 200-room Mount Washington hotel — a National Historic Landmark — or the beauty of the surrounding White Mountains.

12. Yale Golf Course — Number 9 — Par 3, 185 yards

Peter and Maria Hoey

> New Haven, Connecticut; Private

Perhaps the best Biarritz green in the world. What’s a Biarritz? It’s a long green with a pronounced swale or dip near the middle of the putting surface. In the case of this classic — built in 1926 by course architects Seth Raynor and C. B. Macdonald — an 8-foot-deep depression dominates a green that is an incredible 65 yards long. Depending on which side of the swale the flag is positioned on and where your ball ends up — probably not close, since the downhill tee shot measures almost 200 yards and must carry a pond — you could face a putt the length of which you’ve never experienced before, and won’t soon forget.

13. Crumpin-Fox Club — Number 8 — Par 5, 529 yards

Peter and Maria Hoey

> Bernardston, Massachusetts; Public

Ample fairway lies in front of you, but that’s not what grabs your attention when standing on the tee box. The lake that extends all the way down the left side of this hole is impossible to ignore. The green is tucked behind it, forcing a shot over water to reach the putting surface. “Our eighth is definitely one of the best par 5s in New England,” says Jamie Ballard, head golf professional at Crumpin-Fox. “It is a very picturesque hole, a daunting but fair challenge. Many players stop for a photo from the tee box or green.”

14. The Country Club — Number 17 — Par 4, 363 yards

Peter and Maria Hoey

> Brookline, Massachusetts; Private

The 17th certainly isn’t the toughest at The Country Club, or the prettiest. But I’d argue that no hole in New England can match the historical importance of this dogleg left. It was the decisive hole at the 1913 US Open, shockingly won by 20-year-old amateur Francis Ouimet, who could see the hole from his childhood home across the street. It was also where Justin Leonard rolled in a 45-foot birdie putt that clinched the comeback victory for the United States in the 1999 Ryder Cup.

15. Sugarloaf Golf Club — Number 11 — Par 3, 166 yards

Peter and Maria Hoey

> Carrabassett Valley, Maine; Public

Stand on the tee box of this visually stunning hole and you might think you can throw your ball onto the green. That’s because the hole drops considerably and plays much shorter than its stated yardage. Don’t get too confident, though. The Carrabassett River swallows missed shots short or left, while bunkers behind and to the right of the circular green don’t allow for a bailout if your shot sails long. Bring your camera, especially in the fall, when the colors explode and the panoramic vista seduces.

16. Dennis Pines Golf Course — Number 11 — Par 4, 352 yards

Peter and Maria Hoey

> South Dennis, Massachusetts; Public

Sand might be synonymous with Cape Cod, but you won’t find any on this hole. Not one bunker, yet plenty of danger. “A very intimidating tee shot, with water guarding the entire right side and thickly settled trees all along the left,” says Michael Cummings, director of golf at Dennis Golf. Combined with the par-5 12th hole, it’s the start of a one-two punch that can stagger even the best players.

17. TPC Boston — Number 18 — Par 5, 489 yards

Peter and Maria Hoey

> Norton, Massachusetts; Private

When PGA Tour players return to TPC Boston for the Northern Trust tournament next year, the closing hole will test them physically and mentally. Long hitters can reach this green in two shots, but everyone else will lay up short of the hazard that leads into a deep green. As we’ve seen since TPC Boston became a Tour venue in 2003, the 18th hole brings lots of risk, but when two solid shots create an opportunity to make an eagle, it offers plenty of reward.

18. Jay Peak Resort — Number 18 — Par 4, 343 yards

Peter and Maria Hoey

> Jay, Vermont; Public

The course at Jay Peak Resort saves the best for last. This hole, which can play 100 yards longer depending on tee placement, is a twisting dogleg left — and that’s where the trouble lies. Miss it left off the tee or on the approach, and looking for your ball might be a waste of time, because you won’t find it in the woods or tall grass. The narrow fairway leads to an elevated green. It’s a beautiful hole, demanding precision. Anyone making par or better heads to the 19th hole with a well-earned sense of accomplishment.


Adobe Stock; Globe staff illustration

If the holes that make up the Dream 18 aren’t difficult enough for you, here are three more in New England that are guaranteed to give even the best golfers nightmares.

1. If you dare to tee off from the Tiger tees on The Pines course at The International in Bolton, Massachusetts, you’ll be playing what the club describes as the longest golf course in the United States, at 8,325 yards. With that length, there can’t be even one easy hole — and there isn’t. When you get to the fifth hole, that’s not a misprint: The par-5 actually measures 715 yards. Good luck!

2. History is front and center at Kebo Valley Golf Club in Bar Harbor, Maine, a public course which dates to 1888 and is the eighth-oldest golf club in the country. For well over 100 years, the eighth hole has been giving golfers fits. The par-4 is 435 yards, with an elevated tee and a wide fairway. Then it toughens up. The green slopes left toward a brook, so shots sent that way often find a watery grave.

3. As for the toughest par-3 in New England, let’s head up to the North Shore, to Myopia Hunt Club, where good things come in small packages. The ninth hole might not pack a punch in length; at just 130 yards, it’s no more than a pitching wedge for many. But the tiny green is less than 10 paces wide, with seven — count ’em, seven — deep bunkers surrounding it. If you can avoid the danger and find the green, you’ll have a great look at birdie. Easier said than done.

Michael Whitmer is a former Boston Globe sportswriter. Send comments to magazine@globe.com. Get the best of the magazine’s award-winning stories and features right in your e-mail inbox every Sunday. Sign up here.