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Connecticut, Rhode Island and Montauk

Mystic seaport, Newport’s mansions and the ferry to the tip of Long Island.

Distance
333 km (207 mi)
Driving
3 h 41 min
Suggested days
3
Stops
6
States
NY, CT, RI
Updated
July 7, 2026

At a glance: 3-day road trip of about 333 km (207 mi) with 6 stops, from New York to Newport Cliff Walk. About 3 h 41 min of driving in total.

Route description

From New York, take the Long Island Expressway and NY-27, the Montauk Highway, east through the Hamptons to Montauk. At the eastern tip of Long Island, Montauk Point Lighthouse, New York’s oldest, was authorized under George Washington and stands on a bluff above the Atlantic. Montauk itself is a fishing and surf town with good beaches.

For Connecticut, drive back west and around to Orient Point, at the end of the North Fork, where a car ferry crosses Long Island Sound to New London. Reserve a place in advance, especially for a motorhome, as fares depend on vehicle length. From New London, it is a short drive to Mystic, whose seaport museum includes a recreated 19th-century village and the Charles W. Morgan, the last wooden whaling ship.

US-1 continues east into Rhode Island, and RI-138 crosses the Jamestown and Newport bridges to Newport, where the Newport Bridge is a toll bridge. Newport’s Gilded Age mansions, such as The Breakers and Marble House, can be visited, and the Cliff Walk runs past their lawns above the ocean. The southern part of the walk is rough and rocky, so wear sturdy shoes.

Traffic in the Hamptons and on the ferry is heavy on summer weekends, so travel midweek if you can. Parking in Newport is limited, especially for large vehicles. Late spring and September are good times to go, with milder weather and fewer crowds.

Stop-by-stop itinerary

In driving order. Distances are estimates between consecutive stops.

  1. 1

    New York

    NY
    Start
  2. 2

    Montauk

    NY
    211 km
  3. 3

    Montauk Point Lighthouse

    ViewsMontauk, NY

    New York’s oldest lighthouse, at the eastern tip of Long Island.

    11 km
  4. 4

    Mystic

    CT
    39 km
  5. 5

    Newport

    RI
    68 km
  6. 6

    Newport Cliff Walk

    ViewsNewport, RI

    A path along the ocean past the lawns of the Gilded Age mansions.

    3 km