The Great American Road Trip Challenge~4.5 years · 48 states · one loop
The Mid-Atlantic

Stop 2 · Days 85–87

Long Island: The Hamptons & Montauk

Long Island: The Hamptons & Montauk, NY

The island's East End — surf and a historic lighthouse at Montauk, moneyed villages in the Hamptons, and wine country on the North Fork.

Where to stay

  • A Montauk motel or Hamptons inn

    Montauk for a laid-back beach base; the Hamptons for village charm.

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You gotta eat this

  • A Montauk lobster roll & fresh oysters

    Off the docks at the End — plus North Fork oysters.

The days here

Each day opens its own hour-by-hour page

  1. 85Day 85 — Montauk & the EndFull day · 4h planned
  2. 86Day 86 — The Hamptons & North Fork wineFull day · 5h planned
  3. 87Day 87 — Back west & up the HudsonDrive day · 3h 30m drive

What this stop is made of

  • Landmarks & Monuments
  • Outdoor & Water Activities
  • Food & Drink Trails
  • Shopping