Wintonbury Hills offers a nice departure from Pete Dye’s TPC Sawgrass mold into something a bit tamer, but it retains complexity without resorting to an overemphasis on features that once defined Dye’s style - 100-yard-long bunkers, frequent and sinister water-hazards. It is instead the heavily rolling former farmland that everywhere stands out on this striking site for golf. Further, many holes are sprinkled with strategic pot bunkers and the well-contoured greens pose an undeniable challenge. Above all, Wintonbury Hills is sheer fun to play – it’s not a monstrosity – while putting up enough scoring resistance. The only public Dye offering in New England, this layout boasts a quartet of tough and varied par 3s, a pair of rigorous uphill par 4s and a clever, picturesque 14th hole that stretches 455 yards with its driving zone threatened by a right-side water hazard.

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A tasty excursion into the world of Golden Age golf, this Devereux Emmet/Robert "Jack" Ross stunner, reworked in 2015 by Matt Dusenberry, is a complex, unpredictable layout full of clever twists. Setting the tone for a course with strong scoring resistance, the architects built a core of outstanding green complexes. They also used the site’s fantastically rolling terrain to generate strong fairways. They used profuse, deep bunkering and impressive mounding and allowed for big falloffs around many of the greens, which often may leave players in places requiring the highest level of short-game finesse to recover. The greens themselves feature big undulations and ridges, and several are set upon hillocks, most notably at the strong Redan 13th, which punishes weak approaches. Enticing and appealing, but also classically tough and sometimes bewitching, Keney rewards golfers who can accurately place tee shots and dial in approaches, finesse pitch shots and escape deep bunkers, chip well and putt with fine touch. 

Long and forbidding, strategic but also beautiful, this former Travelers Championship qualifying site and Robert Trent Jones, Sr. classic is not only a true driving exam but an equal test of short-game savvy. It’s hard to overcome what you’re immediately subjected to on the rigorous outward half: woods along most fairways; undulating fairway slopes, fringed by fairway traps, that move over hills and through shallow valleys; sprawling, slippery greens menaced by oversized bunkers. Though flatter, the backside is equally bearish, adding three sizable ponds, more gaping bunkers (everywhere, it seems) and some wetlands to avoid, but also several tempting risk-reward holes. It’s a fitting conclusion to a course with grand scale and countryside atmospherics. The most famous Robert Trent Jones adage – “Every hole should be a difficult par but an easy bogey” – seems to echo down the fairways and on the greens of his Lyman Orchards masterwork.

Donald Ross lulls you briefly on Shennecossett’s almost tame opening. What follows what may be the hardest stretch of five holes to par (3 through 7) in all of Connecticut public golf. Having played Shennecosset, Arnold Palmer chose to single out the brutal par-3 fourth, a terrific Volcano hole, describing it as “the easiest par-5 I’ve ever played.” Fortunately, the course’s mood is a bit quieter, if only a tad, on the back, where another rigorous string of Ross holes (10 through 14, which feel links-like) demands great shotmaking. The par-4 16th is long, taxing off the tee and uphill on the approach. Looking every inch the signature hole, it ventures out to the mouth of the Thames River, its green affording a spectacular seaside view to enhance the first-rate golf.

Stealthy rather than flashy, this redesign from Mungeam puts a premium on tee-to-green sharpness – mostly by its strategically-placed bunkers and hilly terrain. Yet the course soothes you with its beautiful backdrops, as the holes seem tailor-made for the handsomely rolling countryside. It's a great blend of modern and classic design: generous, old-school fairways offset by advanced, sculpted green complexes; state-of-the-art greens, lightning-fast and fairly sprawling; classic-looking bunkers. Mungeam has a keen eye for using most bunkers prominently so as to intimidate, especially on the first risk-reward hole (the 3rd, a Cape design), and later on at the par-4 8th, where a pond is further added to the mix, making you think twice about an attempt to drive the green. A track whose difficulty and length favors the strong and the skilled, Connecticut National is still an entertaining odyssey because everything about it feels fresh, varied and stylish.

Mungeam’s early-2000s track has enough great holes to fill three golf courses, a bounty that begins at holes 2 through 4, then puts up strong resistance on 7 through 9 and, over a strategic and hard back-nine stretch, manages to up the ante from 14 to the clubhouse. Sprinkled throughout are clever template-styled holes, each one the architect’s modified take on a classic British type: a Road hole at the 1st; its Biarritz 2nd; its Punchbowl at 11; an exacting Double Plateau green on 12; a subtle Redan at 13; and lastly the par-3 Short that is 16 – a little demon. Many of Oxford’s holes are rugged, but none more so than the steeply uphill and monumentally long 630-yard third, where you’re unlikely to earn a tougher par on a three-shotter. With an array of big challenges and a fine, wooded landscape, Oxford Greens is exciting, strategic and memorable. 

One of the state’s most imaginative layouts and in no way monotonous, Pequabuck treads a tightrope between straightforward American parkland and Golden Age boldness: the fairways are often hilly, mostly tree-lined and lively, but typically generous in width. To be enjoyed here, especially, are thrills from the varied course challenges, like the water-surrounded green at hole 10, sitting intimidatingly below you from its high tee. Holes 11 and 12, both par-4s, can only be beaten by a combination of strategy and sharp shotmaking. Green contours range from subtle to wicked on fast surfaces, yet it is the string of phenomenal holes from 6 through 12 – all terrific from tee to green – which bring the heat while defining the course’s strategic essence. Mainly a test of subtlety over length, Pequabuck is hard to master, but the attempt is the thing. 

Numerous fairway bunkers, many tricky approach shots and speedy greens – these should be enough to satisfy any golfer seeking a stern test at Fairview Farm - but its fairways also bend, curve, rise, pinch tightly threaded tee shots and cascade dramatically, often testing your driver fully. The outstanding green complexes here mostly benefit from big slopes and swales, not to mention some enormous greenside mounds. One favorite hole is no. 15, which is one of the most scenic countryside par-4s I’ve laid eyes on and a joy to play. The second hole, the course's toughest, is a wicked uphill par 4, especially given its fortress-like green that invites three-putting. Not recognized as widely as it should be outside of western Connecticut, Fairview Farm delivers stunning views along with its challenging and varied golf, but above all plays as a first-class strategic test. 

Seth Raynor’s “other” outstanding Connecticut course (the famous one is Yale), is a 9-hole gem tucked in the Litchfield Hills, and will fully engage any serious golfer throughout; it’s a track full of Golden Age challenge and charm. Raynor, a master of template-style holes, made them feel novel here, unveiling a memorable downhill par 3 at no. 8 to a closely guarded green; a rambunctious, twisting roller-coaster ride at the par-5 ninth that punishes errant shots; and a pair of top-notch par 4s at holes one and three, each tumbling energetically over the hilly landscape. The overall tee-to-green test here supplies plenty of punch and is complemented by fast putting surfaces, five plateau greens, and deceptive greenside bunkering. Over nine classically strategic holes, Hotchkiss demands full and unwavering concentration. 

Everything fits at Manchester Country Club: Tom Bendelow’s fine routing with mostly generous fairways; Devereux Emmet’s use of dramatic tee-to-green ground movement; A. W. Tillinghast’s deep and precisely-used greenside bunkers. The course, which benefits from a suitable, smooth blend of Golden Age elements, features multi-faceted greens, some set well above grade, some on hillocks, and still others merging imperceptibly with the terrain; most are nightmarish when you’re above the hole. At the heart of the layout are many strong par 4s, often characterized by elevated, well-protected greens. Most notable is a turbulent green complex at the 12th, a small wonder. Over the last four holes, the course saunters home admirably, culminating in a stern par 4 at no. 17; then succeeded by a long par 3 whose green, nestled against a serene reservoir, ends the round much like it had begun.