Built By Local Professional Caddies

Constructed by local caddies who understand how the Atlantic winds, elevated greens, and ever-changing conditions influence every shot. Their firsthand experience has been transformed into a hole-by-hole strategy designed to help golfers make smarter decisions and play with greater confidence. 

Enhanced by AI

Thoughtfully refined by AI for clarity, organization, and consistency, the guide is easier to prepare with before your round. Every strategy, target, and recommendation is rooted in the firsthand knowledge of experienced local golfers.

HOLE 1 - THE ASCENT
Inviting fairway yields to volcanic summit

Par 4  -  398 / 392 / 365 yds.

Tee Shot
Welcome to what many consider the windiest public golf course in America. At CaddyTips®, we love the wind because it separates golfers who arrive prepared from those who simply hope for the best. Throughout this Playing Guide, you'll learn proven strategies for managing Montauk Downs' ever-changing coastal conditions, but one principle will remain true on every shot: If it's breezy, swing easy.

One of the biggest mistakes golfers make is trying to overpower the wind with an aggressive swing. Overswinging creates poor tempo, tighter grip pressure, and excessive backspin—exactly what the wind wants. Instead, commit to a smooth, balanced swing and trust your club selection. Before your round, spend a few minutes on the practice tee establishing a relaxed tempo, and practice moving the ball slightly back in your stance with your irons to produce a lower, more penetrating ball flight.

Low Handicap: Placement is everything on this opening tee shot. The elevated, volcano-shaped green is much easier to attack with a full wedge than with an awkward half-shot from the rough. While the aggressive line over the left corner may be tempting, it often leaves a difficult uphill pitch with little control. CaddyTips® recommends a fairway wood or hybrid to the right-center of the fairway, setting up the ideal angle for a full wedge and your first birdie.

Mid-High Handicap: Your only objective here is to find the fairway. There is generous room down the right side, so pick a precise target in the right-center and make a confident swing. Teeing your ball on the left side of the tee box naturally encourages a shot toward the safer side of the fairway, while keeping you away from the trouble left. Driver isn't necessary. If your fairway wood or hybrid gives you more confidence, trust it. You'll enjoy a much easier approach from the short grass than from the rough.