The journey from Medford to Montauk spans approximately 115 kilometers along the South Fork of Long Island. You will primarily utilize the Sunrise Highway (NY-27) which transitions into a two-lane road near Amagansett. Driving is the most flexible option, taking roughly 2 hours depending on seasonal traffic. Alternatively, the Long Island Rail Road (LIRR) offers a scenic route from the nearby Medford station with a transfer at Jamaica or Speonk. This route takes you through the heart of the Hamptons before reaching the easternmost point of the island. Expect heavy congestion during summer weekends.
Total Distance: 115 km driving, 105 km air distance.
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Connecting
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Direct
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| Duration | 3 hours 15 mins | 2 hours |
| Avg Price | 20-30 USD | 25-35 USD |
| Operator | LIRR | Personal Vehicle |
| Route | Medford Station to Montauk Station | Sunrise Highway (NY-27 East) |
| Tip | Check the LIRR TrainTime app for real-time track changes at Jamaica. | Avoid traveling on Friday afternoons to escape heavy Hamptons-bound traffic. |
September to October for mild weather and reduced traffic.