The Front Nine

From Rockport to Danbury, New England boasts serious fairways for serious links-lovers. Here, our picks for the region’s most memorable holes.

Any list of the region’s best golf holes is bound to start a spirited debate. Some swingers prefer lots of yardage; some like to keep it short. Many amateurs crave the contest of a curving fairway, while others revel in myriad sand traps. What can’t be disputed, though, is that New England is replete with outstanding options—so many that choosing even the 90 best would be a challenge. Yet we persevered, narrowing it down to the nine most rewarding greens. All are models of innovative architecture and striking scenery—and are just punishing enough to keep golfers hooked drive after drive. So grab your clubs and scorecards, and get ready to take on our dream half-round.

Samoset Resort
Rockport, Maine

Hole 14 / Par-5 / 545 yards

Accuracy is more vital than distance on Samoset’s 14th, where your drive and approach shots need to tunnel through a narrow chute of trees to land on the green. Prone to slicing? All is not lost—get out your camera and capture the view of Penobscot Bay. 220 Warrenton St., 207-594-2511,

Taconic Golf Club
Williamstown, Massachusetts

Hole 12 / Par-4 / 365 yards

Of the state’s 375 courses, Taconic routinely earns high marks for scenic splendor. Its 12th hole combines still beauty with a bit of beastliness: Drive the ball near the “wolf pit” ravine and you might land a good angle from which to hit the green. Swing too aggressively, though, and see your birdie chances swallowed whole. 19 Meacham St., 413-458-9669,

Sugarloaf Golf Club
Carrabassett Valley, Maine

Hole 11 / Par-3 / 216 yards

In the midst of Maine’s High Peaks, Sugarloaf maintains a near-perfect six-hole stretch coined the “String of Pearls” by fabled course designer Robert Trent Jones Jr. The most dramatic is the 11th, an expanse along the Carrabassett River that plays short thanks to a 130-foot drop from tee to green. 5092 Access rd., 207-237-2000,

The Shattuck Golf Club
Jaffrey, New Hampshire

Hole 13 / Par-4 / 315 yards

This course has a well-earned reputation as one of the most challenging in New England—a triple bogey would seem heroic on the 13th hole. A well-struck drive might afford a shot at birdie. Otherwise, it’s trees to the right, water to the left. 53 Dublin Rd., 603-532-4300,

Richter Park Golf Club
Danbury, Connecticut

Hole 12 / Par-5 / 527 yards

The fairway of this par-5 clings to a lake, and the approach shot—to a green horseshoed by water—is about as tough as golf gets. Tougher still? Scoring an invite to the über-exclusive Morefar Golf Club, whose Fortune 500 players can be ogled from Richter’s 12th hole. 100 Aunt Hack Rd., 203-792-2550,

Okemo Valley Golf Club
Ludlow, Vermont

Hole 17 / Par-3 / 213 yards

Vermont native Steve Durkee designed Okemo in ski country and, fittingly, the 17th plays like a black-diamond thrill ride—obstructed by a pond, it sits in a bowl-shaped green. The par-3 calls for a valiant long iron (or a pocket of balls). 77 Okemo Valley Ridge Rd., 802-228-1396,

Yale University Golf Course
New Haven, Connecticut

Hole 9 / Par-3 / 240 yards

The 10-foot swale on the 9th of this A. W. Tillinghast classic is even more imposing than the 200-yard carry over water needed just to reach the green. Should your ball drop on the wrong side of the latter, a four-putt is a distinct likelihood. 200 Conrad Dr., 203-392-2376,

Portsmouth Country Club
Greenland, New Hampshire

Hole 4 / Par-5 / 516 yards

Robert Trent Jones Sr. created this layout on a peninsula, and the fourth hole bends to the left as it’s flanked by open water. You could get home in two, but a greedy shot will leave you all wet. 80 Country Club Ln., 603-436-9791,

Sunday River Golf Club
Newry, Maine

Hole 18 / Par-4 / 443 yards

Surrounded by woods, the closing hole is a downhill dogleg left with trouble all around: an out-of-bounds stretch to the right, trees to the left, and waste bunkers peppered throughout. 18 Championship Dr., 207-824-3000,

Don Jozwiak is the editor of the PGA Professionals’ Guide to Travel.