The opener sets the round’s tone with a generous fairway framed by the course’s natural contours. Favoring the left side provides an ideal angle into a left-to-right terraced green complex. It’s an inviting start from the tee—but the approach demands precision. 

Rooted in appreciation for classic British Isles designs, the second hole embraces influential course architect Tom Simpson’s “drive-and-pitch” philosophy. A drive favoring the left side provides the best angle into a green defended by a steep fall-off on the right side and strategic bunkering.

The first par 5, one of Virginia’s best holes, tumbles downhill, bending around a corner through a corridor of trees, toward a partially hidden landing area guarded by pocketed cross-bunkering. A dramatic railroad cut sunken into the landscape, crosses the fairway 100 yards short of the green, creating both a visual obstacle and strategic decision. The plateau green draws inspiration from James Braid’s famed “Het Girdle” at King’s Course at Gleneagles—Gaelic for “hot griddle.” Don’t miss your mark here, especially long.

The setting for this par 3 traces the edge of the lowlands along Contrary Creek, which flows into nearby Lake Anna. The hole plays along one of Cutalong’s abandoned railway corridors—an enduring reminder of the land’s mining heritage—to a green that draws inspiration from the iconic 17th at Pebble Beach Golf Links. Shaped like a tilted hourglass, the green features a back-left section that sits slightly lower than the front-right, divided by a gentle ridge that adds nuance to both club selection and putting. Missing it in the wrong section can leave a challenging two-putt—making precision and placement essential.

A tribute to legendary architect Pete Dye, this alternate route, drivable short par 4, blends bold visuals with strategic nuance. A long, winding waste bunker guides play from the tee, while a wooden-post bulkhead frames the wetlands hazard on the left. Railroad tie-lined pot bunkers add character and challenge, guarding a distinctive two-pronged green. The pin placement ultimately shapes the strategy, inviting players to choose their line based on the day’s setup. As you leave the green, a peaceful view of Contrary Creek provides a scenic finish to one of the course’s most memorable holes.

The 6th hole unfolds across a beautifully contoured landscape; its undulating fairway climbs to a crest that offers the preferred landing area off the tee. Longer hitters may want to club down to avoid driving through the fairway. Approach shots from the elevated fairway require a forced carry over a deep ravine and stream to a contoured green inspired by the crowned surfaces of Pinehurst No. 2. The hole rewards two well-executed shots yet will be quick to penalize anything less.

Inspired by the classic Wentworth Club (West Course) design by H. S. Colt, the 7th hole features a perched green with a challenging fall-off on the left and a more generous escape route to the right. Guarding the approach, two bold bunkers cut tightly into the slope below the putting surface and bear an uncanny resemblance to the iconic Principal’s Nose at St Andrews Links (Old Course). Now known as Cutalong’s “Principal’s Nose” par 3, this tee shot demands precision.

Cutalong’s longest par 5 rewards patience as much as power. The fairway is guarded along the left by a winding creek that continues to influence play near the green, demanding a thoughtful layup to the proper position and angle. From there, the hole reveals a distinctive V-shaped multi-tiered green inspired by a traditional Redan. Bold golfers can lay up on the left side for a better angle, while conservative players may favor the right for an easier approach.

The longest par 4 on the course relies on landforms and natural rock outcroppings rather than bunkers for defense. Playing steadily uphill, the fairway contour tilts from right to left, subtly gathering tee shots toward a dense outcropping of trees that can quickly turn aggressive lines into blocked approaches. The green reveals itself as a nod to Augusta National Golf Club—a mirrored interpretation of Alister MacKenzie’s iconic 14th with bold plateaus and sweeping ridges.

Cutalong’s shortest par 4 plays downhill to a full Redan character, with the fairway and green tilting from front left to back right. While many will be tempted to take on the green, holding the surface can be challenging. The smartest line is left of the green, using natural contours to feed the ball toward the green, setting up a scoring opportunity.

The par-5 11th sweeps through the landscape in a distinctive fishhook shape, demanding precision. For most, it’s a true three-shot hole, as a diagonal stream cutting across the fairway beyond the crest forces players to think twice about overpowering the drive. Longer hitters who challenge the line are met with a narrow approach framed by towering trees along the right, favoring a controlled fade for any chance to reach in two. The hole finishes uphill to a green inspired by classic English designs, placing a premium on distance control and a well-judged approach.

Paying homage to the classic Biarritz—an iconic design popularized by C.B. Macdonald—the 12th features a long, narrow green split by a dramatic central swale, creating distinct front and back plateaus. It adds a unique twist, with the green set at an angle to the line of play, subtly complicating both distance and alignment.

The 13th presents a beautifully balanced test of angles. The fairway tilts left to right, guiding tee shots toward a preferred line down the left side and challenging the bunkers to find the best angle in the fairway. From there, the approach carries a rising slope framed by a striking trio of bunkers that form a natural open runway into the green. Set on a gentle plateau, the green is deceptive. With no surrounding bunkers, it sports a pronounced fall-off to the right and a defined central spine that influences every putt.

This hole stands as one of Cutalong’s most compelling and memorable holes, blending Golden Age inspiration with the land’s rugged mining past, while drawing inspiration from Talking Stick North, Prairie Dunes, and the famed Road Hole at St. Andrews. The preferred line challenges players up the left with a risk-reward shot, carrying cross bunkers to a partially hidden fairway. Drift too far left, and you’ll encounter a dramatic remnant of the property’s history—a 10-foot-deep railroad cut, now transformed into a rugged strip bunker. To the right, the land reveals another piece of Cutalong’s past—an old mine site, now resting quietly in the rough, adding both character and caution to any miss in that direction. The approach narrows as it climbs toward a green modeled after Road Hole’s iconic 17th, defended by a penal pot bunker and subtle angles that reward precision.

A compelling choice from the tee offers two distinct routes to the green. The prudent play favors the left, where a well-placed drive opens up a clean approach. For those chasing an advantage, the aggressive line challenges the MacKenzie-inspired bunkers on the right, rewarding a drive with a shorter, partially obscured pitch over a subtle rise. The green itself rests in a classic punchbowl—reminiscent of the 16th at National Golf Links—with a tightly mown slope on the right that gathers and guides shots toward the hole.

A blind drive plays over a tilted hillside into a wide fairway. From there, the hole’s true defense reveals itself. An elevated green set beyond a natural hollow demands a fully committed approach. The putting surface is anything but simple, featuring subtle contours and runoffs that make distance control critical. Miss long, and a sharp falloff leaves a delicate recovery, turning this hole into a true test of precision.

Inspired by Alister MacKenzie’s famed Gibraltar hole at Moortown, the 17th reinterprets the original’s distinctive bunker scheme—perched high right and low left—to quietly shape strategy and shot selection. The challenge lies solely in contours and angles, requiring accuracy and proper club selection. A miss to the left provides the easiest up and down, but a miss high and right will challenge the best short games.

Inspired by the iconic 18th at Shinnecock Hills Golf Club, Cutalong’s own finishing hole plays uphill toward the Clubhouse, delivering a dramatic scene. It is one of the course’s most heavily bunkered holes, including a central target bunker and a string of five along the left that shape both strategy and sightlines. The approach into a small, diagonal green demands total precision. From tee to green, every shot is a challenge, making this a memorable finale.