New York to Southampton Road Trip Guide: Coastal Escape

On the morning of August 29, 1960, the first section of the Long Island Expressway (I-495) opened, forever changing travel from New York City to the eastern shores of Long Island. This road trip from Manhattan to Southampton, NY, is a journey through suburban sprawl, pine barrens, and finally, the opulent coastal towns of the Hamptons.

• Total distance: approximately 95 miles (153 km).
• Estimated driving time: 1 hour 45 minutes without traffic; plan for 2.5 to 3 hours during peak summer weekends.
• Route: I-495 East (Long Island Expressway) to CR 111, then NY-27 East (Sunrise Highway) to Southampton.

For a deeper dive on discovering hidden gems along any route, check out how to find the best stops and hidden gems between cities.

The Long Island Expressway is rated among the top 10 most congested highways in the US, and aggressive driving is common. Use the right lane except to pass. Sheep-pasture-style median barriers reduce crossover collisions, but wildlife (deer) can be an issue in the Pine Barrens at dawn/dusk. Road safety and quality: Pavement is generally good but watch for potholes in spring. Speed cameras operate near construction zones.

• Family stops: Long Island Children's Museum in Garden City (11 Davis Ave; $15; ages 1-17). Indoor interactive exhibits on bubbles, communication, and climbing structures.
• Pet-friendly framework: Most rest areas on the LIE have pet-walk areas. The East End portion of the trip has many dog-friendly beaches (Coopers Beach in Southampton allows dogs off-season; on-leash before 9 am and after 5 pm in summer).
• Fatigue management: Stop at the Dix Hills Rest Area (milepost 51) on the eastbound LIE, open 24/7. It has a convenience store, restrooms, and picnic tables. Alternatively, the Suffolk County Nature Center in Ridge (a few miles north of exit 57) offers quiet walking trails to refresh.

Hidden off-route spots: The Caleb Smith State Park Preserve in Smithtown (off exit 56) is a serene 543-acre haven with easy walking trails and a pond. Less known is the Big Duck in Flanders (231 Montauk Highway), a 20-foot-tall concrete duck built in 1931, listed on the National Register of Historic Places. It's a quirky photo op and sells duck memorabilia. For a true detour, take CR 105 to the small fishing village of Greenport, with its historic carousel and roadside clam shacks.

The drive transitions from the skyscrapers of Manhattan through the low-rise suburbs of Queens, then into the terminal moraine of Long Island's spine: rolling hills covered in oak and pitch pine. The most dramatic landscape is the Pine Barrens region around exit 53, a 100,000-acre state preserve with deep green forests and cranberry bogs. Stop at the Wertheim National Wildlife Refuge on the south shore for walking trails and birding.

• Wertheim National Wildlife Refuge: Located off William Floyd Parkway; free entry. Open daily sunrise to sunset. Kayak rentals available at adjacent Forge River Marina.
• Suffolk County Farm and Education Center: In Yaphank; farm animals, hayrides, and a corn maze (seasonal). Contact (631) 852-4600.
• Local commerce: In Southampton, the main shopping strip on Jobs Lane features high-end boutiques (Tory Burch, Ralph Lauren) and antiques. For local flavor, walk through the Southampton Farmers Market (Saturdays May-November, on North Sea Road).

Cultural note: Southampton was founded in 1640 by English settlers, and historic Whaling Captain's houses dot the village. The Southampton Historical Museum on Meeting House Lane (open Tue-Sat 10-4, $5 admission) details the town's colonial and whaling past. For contemporary art, the Parrish Art Museum in nearby Water Mill (279 Montauk Highway) houses a stellar collection of Long Island artists.

The artery is the Long Island Expressway (I-495), a six-to-eight-lane highway that narrows to four lanes past exit 64. Congestion is severe near the Nassau/Suffolk border, especially at the merge with the Northern State Parkway. The alternative, NY-27 (Sunrise Highway), is a surface road with traffic lights from exit 38 eastward, but it offers quicker access to south shore beaches.

• Fuel: Gas stations are abundant every few exits. Prices tend to be higher in Suffolk County; fill up in Melville or Farmingdale. Costco and BJ's Wholesale Club in Medford offer discounted fuel for members.
• Tolls: Only the Southern State Parkway (unmetered) is toll-free; I-495 has tolls only if using the Midtown Tunnel ($7.00 each way). The LIE itself has no tolls.
• Electric vehicle charging: Tesla Superchargers at the South Bay Shopping Center in Bay Shore (171 min) and at the Southampton Village Green. Multiple Electrify America stations in Riverhead.

Route economics: The direct cost for a round trip in a sedan (25 mpg) at $4/gallon is about $30 in fuel. Tolls and parking in Southampton (paid lots average $20/day) add to the trip. Consider a group share via the Hampton Jitney for a stress-free alternative, but driving gives flexibility to explore things to do between New York, NY and Southampton, NY.