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The End — Montauk

Last stop on the LIRR, first light in New York State.

7 stops · 95 points ⏱ Full day — train + legs, or car 📍 Meet: Montauk LIRR Station, Flamingo Ave 🎟 Free pilot — bragging rights on the line

Montauk is where New York runs out: the easternmost train station on the LIRR — 118 miles from Penn Station — and the lighthouse George Washington authorized in 1792, first lit when the republic was younger than your phone. In between: surf at Ditch Plains, a Cold War radar that started a thousand legends, and the sunset the whole island turns out for. Take the train out if you can — arriving at The End by rail is the point.

The stops

1
End of the Line15 pts
Flamingo Ave, Montauk, NY 11954

The easternmost station in New York — 118 miles from Penn. Photo at the platform's end-of-track bumper; +10 if your team actually arrived by train.

2
The Montauket10 pts
88 Firestone Rd, Montauk, NY 11954

The sunset institution on Fort Pond Bay. Toast the horizon from the deck — the whole island shows up for this one.

3
Gosman's Dock10 pts
500 W Lake Dr, Montauk, NY 11954

The harbor inlet where the fleet comes home. Photo with a working fishing boat passing the jetty.

4
Ditch Plains10 pts
Ditch Plains Rd, Montauk, NY 11954

The East Coast's most famous longboard break. Surf-check photo: team lined up reading the waves like locals.

5
The Hoodoos10 pts
Shadmoor State Park, Montauk Hwy, Montauk, NY 11954

Clay hoodoos and a hundred-foot ocean view. Panorama from the bluff platform — respect the edge.

6
The Radar15 pts
Camp Hero State Park, Montauk, NY 11954

The Cold War AN/FPS-35 radar dish that launched a thousand conspiracy theories (and a certain TV show). Photo from the marked trails — the fences mean it.

7
The Light25 pts
2000 Montauk Hwy, Montauk, NY 11954

Authorized by George Washington in 1792 — the oldest lighthouse in New York, the first thing home ships saw. Full team at the base + one lighthouse fact on video. You are now officially at The End.

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