How It Works

CaddieTrail is a pursuit platform for golfers who take their course list seriously. We organize the world's greatest golf courses into curated Trails — and give you a way to track, complete, and share your progress across all of them. Think of it as your golf résumé, your bucket list, and your personal leaderboard. Once you're on the platform, you build a circle of golfers you follow — and a friend leaderboard tracks where everyone stands across every trail you're chasing. Some will take years to finish. That's the point.

Every trail is a curated collection of courses grouped around a common theme — the best courses in a state, the defining works of a legendary architect, the iconic destinations every serious golfer has on their list. Trails have a defined course list, a difficulty rating, and a finish line. Complete all the courses on a trail and you own it forever.

CaddieTrail currently features 65+ trails across six categories:

• State Trails — The top courses in each state, built for golfers working their home region
• Flagship Trails — Signature collections of the most celebrated courses in golf
• Architect Trails — The defining works of legends like Pete Dye, Donald Ross, Alister MacKenzie, and more
• Destination Trails — Iconic golf destinations worth planning a trip around (Pebble Beach, Bandon Dunes, and beyond)
• International Trails — The greatest courses outside the US, from the Scottish Links to Ireland's finest
• Signature Trails — Curated collections that don't fit a single state or destination but belong together

CaddieTrail rankings are built from multiple respected golf ranking sources — specifically Golf Digest and Golf.com — cross-referenced, weighted, and filtered through a set of guardrails designed to ensure every course on a trail is both genuinely great and actually playable. We don't rely on any single list. Courses that rank well on prestige alone but aren't accessible to real golfers don't make the cut. Trail compositions reflect 2026 ranking data.

Trail compositions are based on current ranking data at the time of each edition. As source rankings evolve, CaddieTrail will review and update trails accordingly — though the timing and cadence of updates hasn't been finalized yet. What won't change: if you've already checked in a course that later moves off a trail, your check-in is preserved. Your history is always yours.

Complete every course on a trail and you've completed it. You'll earn a Trail Completion Badge, it goes on your trophy wall, and it stays there permanently. Some trails have 10 courses. Some have 50. The harder the trail, the more it means to finish it. There's no time limit. Some trails will take years. That's the point.

Not yet. Custom trails are on the roadmap. For now, CaddieTrail's value is in the curation — trails built with a defined methodology, not personal preference. When custom trails launch, you'll be able to build and share your own collections with your circle.

CaddieTrail's course database covers the top-ranked courses across all 65+ trails. If a course you're looking for isn't listed, it's likely because it doesn't currently appear in our ranking sources — but we're always expanding. Use the course suggestion feature in your profile to flag missing courses and we'll review them for inclusion.

Free accounts can pursue up to 2 trails, mark courses as played, and build their golf résumé. Member accounts unlock unlimited trail pursuits, Architect and International trails, full play history, and unlimited leaderboard access. See the full comparison on our Pricing page.

Founding Member pricing — currently $19.99/year — locks your rate for life and is available through October 31, 2026.

Founding Members are the golfers who believed in CaddieTrail early. Your $19.99/year rate is locked for life — it will never increase as long as your membership is active. You'll also receive a permanent Founding Member designation on your profile and a unique member number (CT-XXXX) that reflects when you joined.