Getting to (and around) the Hamptons

The four spinal roads

Every East Ender memorizes these. Find one and you can navigate anywhere.

• Route 27

  Also known as: Sunrise Highway · Montauk Highway

  Route: Manhattan (via Sunrise Hwy) -> Westhampton -> Southampton -> East Hampton -> Amagansett -> Montauk Point

  The single road that runs the length of the South Fork from Manhattan all the way to Montauk Point. Becomes Sunrise Highway in central Long Island, then Route 27 east of the Shinnecock Canal, then 'Montauk Highway' colloquially east of Southampton. If you get lost on the South Fork, find Route 27 and it will get you anywhere from Westhampton to the lighthouse. Two lanes most of the way. Backups every Friday afternoon and Sunday evening, Memorial Day through Labor Day.

  Hamlets: Westhampton, Hampton Bays, Southampton, Water Mill, Bridgehampton, Wainscott, East Hampton, Amagansett, Montauk

• Route 25

  Also known as: Main Road

  Route: Riverhead -> Aquebogue -> Jamesport -> Mattituck -> Cutchogue -> Peconic -> Southold -> Greenport -> East Marion -> Orient -> Orient Point

  The North Fork's spinal road, running from Riverhead east through every wine-country village to Orient Point and the Cross Sound Ferry. Slower than Route 27 because every village has a Main Street that becomes a 25 mph zone. This is the only North Fork road you need.

  Hamlets: Riverhead, Aquebogue, Jamesport, Mattituck, Cutchogue, Peconic, Southold, Greenport, East Marion, Orient

• Route 24

  Also known as: Riverhead-Hampton Bays Road

  Route: Riverhead (Route 25 junction) -> Flanders -> Hampton Bays (Route 27 junction)

  The connector between Route 27 (South Fork) and Route 25 (North Fork) at the Riverhead end. If you're crossing between forks by car without using the Shelter Island ferries, this is the route. Passes Riverhead traffic circle and the Big Duck.

  Hamlets: Riverhead, Flanders, Hampton Bays

• Old Montauk Highway

  Also known as: Old Montauk Hwy

  Route: Amagansett (Napeague) -> Hither Hills -> Montauk Village

  The pre-1960s scenic alternative to Route 27 between Amagansett and Montauk. Bluff-side, two lanes, no shoulder, drops down past roadside motels to ocean beaches. Slower but spectacular. Locals use it on summer Sundays to skip the Route 27 crawl.

  Hamlets: Amagansett, Napeague, Montauk

Cross-roads and back-routes

North-south connectors between Route 27 and the bay, plus the lesser-used alternates locals take when the main roads jam.

• North Sea Road

  Southampton Village -> North Sea -> Peconic Bay

  The main Southampton-to-bay connector, running from Southampton Village north to the hamlet of North Sea on Peconic Bay. Feeds into Noyack Road at its north end.

• Noyack Road

  Sag Harbor -> Noyack -> North Sea (connects to North Sea Road)

  The bay-side connector between Sag Harbor and Noyack, continuing west into North Sea Road toward Southampton. Passes Jessup's Neck and Morton Wildlife Refuge.

• Sag Harbor-Bridgehampton Turnpike

  Bridgehampton (Route 27) -> Sag Harbor

  The most-used cross-fork connector for South Fork residents. Runs from the Bridgehampton Commons/Route 27 straight north into Sag Harbor Village. Jams solid on summer weekends around the Sag Harbor end.

• Scuttle Hole Road

  Bridgehampton -> Sagaponack potato fields -> Water Mill (via Mecox)

  The Bridgehampton-to-Sag Harbor alternate that runs north of the turnpike through potato fields. Less traffic, no commercial strip, the locals' back route when the turnpike is jammed.

• Two Rod Highway

  East Hampton -> Springs

  East Hampton Village to Springs alternate. Narrow two-lane, scenic, runs parallel to Springs-Fireplace through the woods.

• Springs-Fireplace Road

  East Hampton Village -> Springs (Pussy's Pond / Ashawagh Hall)

  The more-used Springs connector. Runs from East Hampton Village north-northeast past Springs School, the library, and the General Store. The spine of the Springs community.

• Abraham's Path

  East Hampton -> Amagansett (parallel to Route 27, north side)

  Parallel alternate to Route 27 between East Hampton and Amagansett. Less traffic, passes through woods and horse country. Use when Route 27 is backed up east of the village.

• Three Mile Harbor Road

  East Hampton Village -> Three Mile Harbor -> Maidstone Park -> Cedar Point

  The bay-side road out of East Hampton Village. Runs north to Three Mile Harbor marina and continues to Maidstone Park and Cedar Point County Park. The only road to Cedar Point.

• Old Stone Highway

  Amagansett -> Springs (scenic alternate)

  Scenic alternate from Amagansett north into Springs. Narrow, winding, passes through Accabonac Harbor wetlands and the Springs art community.

• Napeague Meadow Road

  Amagansett (Napeague stretch) -> Montauk

  Sand-strip alternate to Route 27 across Napeague. Runs through the meadows and dune-grass flats between Amagansett and Hither Hills. Tidal flooding possible at the extreme ends.

Ferries

Water crossings between the forks and off the East End entirely.

• North Ferry

  Greenport (North Fork) <-> Shelter Island Heights \u00b7 7 minutes \u00b7 North Ferry Company

  Drives on, drives off. Every 10-15 minutes during daylight hours year-round. The connector between the North Fork and Shelter Island. Short enough to feel like a bridge.

• South Ferry

  North Haven (Sag Harbor) <-> Shelter Island (South Ferry Hills) \u00b7 10 minutes \u00b7 South Ferry Inc.

  Drives on, drives off. The South Fork's connector to Shelter Island. Paired with North Ferry it lets you cross from the South Fork to the North Fork by car without going all the way around through Riverhead.

• Cross Sound Ferry

  Orient Point -> New London, Connecticut \u00b7 80 minutes \u00b7 Cross Sound Ferry Services

  The only way off the East End by water without going through Manhattan. Carries cars and passengers across Long Island Sound to New London. High-speed passenger-only option also runs seasonally.

• Shelter Island Freight

  Greenport <-> Shelter Island Heights (same crossing as North Ferry) \u00b7 7 minutes \u00b7 North Ferry Company

  Larger vessels on the North Ferry crossing to carry trucks, propane tankers, landscaping trailers, and construction equipment that the passenger boats can't. Same route, same schedule window, different boats.

GPS gotchas

Places turn-by-turn routinely gets wrong. Learn them before you rely on your phone.

• Springs has multiple Springs-Fireplace Roads

  The Springs road network is a tangle. Turning the wrong way at an intersection puts you in Three Mile Harbor instead of Springs Village. If GPS says 'turn right on Springs-Fireplace' and you're already on Springs-Fireplace, stop and look at a paper map.

• Old Montauk Highway disappears into Route 27

  Old Montauk Hwy rejoins Route 27 twice between Amagansett and Montauk (at the west end near Napeague and again near Hither Hills). Easy to overshoot the scenic detour entrance if you're not looking for it. Watch for the brown 'scenic route' sign.

• Mecox Road dead-ends at the beach

  Mecox Road in Water Mill ends at the ocean with no through-road signage. GPS happily routes you there thinking it's a thru-road to Sagaponack. It is not. You will have to turn around.

• Sagg Main vs Sagg Pond Road (Sagaponack)

  Both roads in Sagaponack lead toward the ocean but they are different roads and neither connects to the other at the beach end. GPS systems have been known to confuse them. Sagg Main goes to Sagg Main Beach; Sagg Pond Road goes to the pond.

• The North Haven Bridge

  The bridge from Sag Harbor to North Haven (leading to the South Ferry) is a single lane each way with no alternative. On summer weekends traffic backs up onto Long Wharf and can take 30 minutes to clear. No GPS warning for this; locals just leave earlier.

Landmarks for wayfinding

Visible anchors you can orient from without opening a map.

• Sag Harbor Windmill (Long Wharf)

  Sag Harbor

  The small windmill at the head of Long Wharf. The entire village navigates from here: 'two blocks back from the windmill,' 'the side of the windmill.' If you can see it, you know where you are.

• Bridgehampton Commons

  Bridgehampton

  The only proper strip mall between Southampton and Amagansett. The canonical 'halfway between South Fork hamlets' landmark. If you see the King Kullen sign from Route 27, you're at Bridgehampton.

• East Hampton Village Green and Windmill

  East Hampton

  Town Pond, Hook Windmill, the Old Burying Ground, and the village green form the historical center of East Hampton. Every street in the village radiates from here. Route 27 bends around it.

• Maidstone Club

  East Hampton

  The private golf club marking the easternmost edge of East Hampton Village. Beyond it on Route 27 you are leaving the village and heading toward Amagansett. A useful 'am I still in town?' marker.

• Shinnecock Canal Bridge

  Hampton Bays

  The dividing line between 'the Hamptons' and 'up-island.' Route 27 crosses the canal here at the Hampton Bays / Southampton town line. Once you're east of the canal you are formally in the Hamptons.

• Hither Hills State Park entrance

  Montauk

  The Route 27 entrance to Hither Hills State Park. When you see the park entrance sign, you are 5 minutes from downtown Montauk. A mental waypoint that's more reliable than GPS in the dropout zone.

• Montauk Point Lighthouse

  Montauk

  The literal end of the road. Route 27 terminates at the lighthouse parking lot. If you are still driving east at the lighthouse you are in the Atlantic Ocean.

• Greenport Mitchell Park and Carousel

  Greenport

  The waterfront park with the historic carousel in its glass pavilion. The center of Greenport village. Orient yourself here: Front Street is two blocks inland, the Cross Sound Ferry is further east on Route 25, North Ferry is a block west.

Cell signal dead zones

Where you’ll lose data. Cache offline maps before you enter these areas.

• Montauk (Camp Hero / Hither Hills)

  Signal is spotty everywhere in Montauk and goes fully dead in pockets near Camp Hero State Park and through the wooded stretches of Hither Hills. Download offline maps before you leave Amagansett.

• Napeague stretch (Amagansett to Montauk)

  Frequent signal dropouts along the 7-mile Napeague stretch where Route 27 crosses open meadows and dune flats with no cell infrastructure. Turn-by-turn navigation will hang. Use pre-loaded offline maps.

• Mashomack Preserve (Shelter Island)

  No signal on most of the Mashomack Preserve trail network. If you are hiking the preserve, tell someone your plan before you go in and carry a printed trail map from the visitor center.

• Hallock State Park Preserve (North Fork)

  Minimal to no signal through the interior of Hallock State Park Preserve on the Long Island Sound side of the North Fork. The beach trail has no bars.

• Cedar Point County Park (East Hampton)

  Minimal signal throughout Cedar Point County Park. The only road in/out is Three Mile Harbor Road, which also loses reception in stretches. Cache the route before you drive in.

• Robins Island and open Peconic Bay water

  No land-based cell coverage out on open Peconic Bay water, including around Robins Island. Boaters should carry a VHF radio, not rely on phones.

Who can fly?

Six access tiers from full FBO membership down to no realistic air option at all.

1. Tier 1 — Full FBO access

   Who: Private jet owners, NetJets / Wheels Up / fractional members, charter clients on a real broker

   Access: KHTO (when PPR allows), KFOK, KISP, KFRG. Broker handles slots, slots handle you.

2. Tier 2 — Per-seat helicopter

   Who: Anyone with a credit card and the Blade app

   Access: Manhattan ↔ KHTO summer schedule, ~$1,000 one-way. Books like an Uber. Lands at the public airport.

3. Tier 3 — Per-seat seaplane

   Who: Anyone with a credit card and the Tailwind / Shoreline app

   Access: Manhattan ↔ Sag Harbor / East Hampton water, ~$795 one-way. Weather-cancelled more often than helo.

4. Tier 4 — Empty leg / charter quote

   Who: Anyone willing to call a broker and wait

   Access: Talon Air, Saker, Helo Holdings will quote ad-hoc charters. KHTO PPR-only for non-members. Pricing on application.

5. Tier 5 — Commercial-airport drive-in

   Who: Anyone flying commercial into NYC

   Access: Land at JFK / LGA / EWR (reference only — not Hamptons airports), then 2.5–4 hours of car or jitney to the East End.

6. Tier 6 — No realistic air option

   Who: Travelers without the budget or the broker

   Access: The honest answer: take the LIRR Cannonball or the Hampton Jitney. Both are above. The Air section is here for context, not as the default path.

Every airport, mapped