Block Island to Southampton: Coastal Drive Guide

Most travelers begin this route on Block Island, taking the year-round ferry from Old Harbor to Point Judith, RI. The drive then winds through southern Rhode Island and Connecticut before crossing into New York via the Orient Point ferry (Cross Sound Ferry) or, more directly, via the Long Island Expressway (I-495) after crossing the Throgs Neck Bridge. The total drive time, excluding ferries, is approximately 4 to 4.5 hours, but with waiting and crossing times, plan for 6 to 8 hours.

A little-known historical fact: The Montauk Point Lighthouse (1797) at the eastern tip of Long Island is the fourth-oldest active lighthouse in the United States and marks the final point of this journey. The route traverses the terminal moraine of the last glacial period, leaving a landscape of rolling hills, kettle ponds, and sandy beaches.

The primary road from Point Judith is US-1 south, which merges into I-95 in New Haven, CT. For the Orient Point ferry, take CT-9 south to I-95, then exit for NY-25 east. The Cross Sound Ferry runs from New London, CT to Orient Point, NY (80 minutes, $50-70 for car and driver).

• Fuel stops: Avoid filling up on Block Island (prices ~$1 more per gallon). Best stops in Rhode Island (Exit 3A on I-95, Richmond) and Connecticut (Exit 74, Clinton).
• Tolls: I-95 in Connecticut has tolls (pay by plate); bridge tolls on Throgs Neck ($9.50) if not using Orient ferry.
• Ferry reservations: Recommended for summer weekends; book at least 2 weeks ahead.

The Orient Point ferry eliminates heavy traffic around New York City but adds time. Alternatively, drive via I-95 and the Throgs Neck Bridge to the LIE, then east on Sunrise Highway (NY-27) to Southampton. This route bypasses ferry lines but may encounter congestion near the city. Check traffic via Waze or NY511.

Driving across Rhode Island, you’ll see the Great Swamp Management Area (a massive freshwater marsh) and the coastal salt ponds of Charlestown. In Connecticut, the shoreline along US-1 offers views of Long Island Sound, with small harbors and marinas.

• Best landscape stops: Bluff Point State Park (Groton, CT) for coastal views; Rocky Neck State Park (East Lyme, CT) for a sandy beach.
• Hidden gem: Barn Island Wildlife Management Area (Stonington, CT) — explore old stone walls and tidal marshes.

Local commerce thrives in towns like Mystic, CT (famous for Mystic Pizza and the seaport) and on Long Island’s North Fork, known for farm stands and wineries. The South Fork toward Southampton becomes more affluent, with antique shops and art galleries.

For tips on finding hidden gems during long drives, see how to find the best stops and hidden gems between cities.

Road quality is generally excellent on interstates, but secondary roads in rural Connecticut may have narrow, winding sections. Deer crossings are common at dawn and dusk, especially near wooded areas. Use high beams on unlit sections.

• Safety: Connecticut law requires hands-free devices; speed cameras are active in work zones.
• Family stops: Children’s Museum of Southeastern Connecticut (Niantic); Lyman Allyn Art Museum (New London) has a hands-on discovery room.
• Pet-friendly: Harkness Memorial State Park (Waterford, CT) allows dogs on leash; Montauk Point State Park does too.

To combat fatigue, plan a break every 2 hours. Rest stops on I-95 at Madison (CT) and Westbrook (CT) have clean facilities and vending. After the Orient ferry, the rest area on NY-25 in Greenport (about 10 miles west) offers picnic tables. For a longer stop, consider the town of Riverhead (Suffolk County), with parks and the Long Island Aquarium.