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: Brooklyn (Gowanus) -> Sunrise Highway -> Westhampton -> Southampton -> East Hampton -> Amagansett -> Montauk Point

  The single road that runs the length of the South Fork. Its western end is in Gowanus, Brooklyn, not Manhattan — Route 25 is the one that reaches Manhattan. Eastern end is 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. 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

  Source: openstreetmap.org

• 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. The state route itself carries on west all the way to Manhattan. 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

  Source: openstreetmap.org

• 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. The state route runs much further west than Riverhead — its other end is in Queens — but the East End stretch is the useful part.

  Hamlets: Riverhead, Flanders, Hampton Bays

  Source: openstreetmap.org

• 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, posted 30 mph, no shoulder, drops down past roadside motels to ocean beaches. About 6.5 km end to end. Slower but spectacular. Locals use it on summer Sundays to skip the Route 27 crawl.

  Hamlets: Amagansett, Napeague, Montauk

  Source: openstreetmap.org

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 7.7 km from Southampton Village north to the hamlet of North Sea on Peconic Bay. Signed County Road 38. Feeds into Noyac Road at its north end.

  Source: openstreetmap.org

• Noyac Road

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

  The bay-side connector between Sag Harbor and Noyac, continuing west into North Sea Road toward Southampton. Spelled 'Noyac' on the road signs and in the state and OSM records, though 'Noyack' is common locally for the hamlet. Passes Jessup's Neck and Morton Wildlife Refuge.

  Source: openstreetmap.org

• Bridgehampton-Sag Harbor Turnpike

  Bridgehampton (Route 27) -> Sag Harbor

  The most-used cross-fork connector for South Fork residents. Runs 5.7 km from the Bridgehampton Commons/Route 27 straight north into Sag Harbor Village, signed County Road 79, two lanes, posted 35 mph. Jams solid on summer weekends around the Sag Harbor end.

  Source: openstreetmap.org

• Scuttle Hole Road

  Water Mill (Hayground) -> potato fields -> Bridgehampton

  The back route across the fields between Water Mill and Bridgehampton, running 7.2 km north of Route 27 and posted 40 mph. Less traffic, no commercial strip. It does not itself reach Sag Harbor or Sagaponack — for Sag Harbor you pick up the Bridgehampton-Sag Harbor Turnpike at the Bridgehampton end.

  Source: openstreetmap.org

• Two Rod Highway

  Wainscott (Midhampton) local street

  Worth knowing chiefly so you don't go looking for it as a shortcut: Two Rod Highway is a 530-metre residential lane in the Midhampton part of Wainscott, posted 30 mph. Despite the name it is not a highway and not a through route to Springs. For East Hampton to Springs use Springs Fireplace Road.

  Source: openstreetmap.org

• Springs Fireplace Road

  East Hampton North (Freetown) -> Springs (Pussy's Pond / Ashawagh Hall) -> Fireplace

  The more-used Springs connector, 9.6 km and signed County Road 41. Runs from the Freetown edge of East Hampton north-northeast past Springs School, the library, and the General Store, ending at Fireplace. The spine of the Springs community.

  Source: openstreetmap.org

• Abrahams Path

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

  Parallel alternate to Route 27, running 4.2 km from the Springs side down into Amagansett. Less traffic, passes through woods and horse country, posted 30 mph. Use when Route 27 is backed up east of the village.

  Source: openstreetmap.org

• Three Mile Harbor Road

  East Hampton North (Freetown) -> Three Mile Harbor -> The Creek (continues as Three Mile Harbor Hog Creek Road to Maidstone Park)

  The bay-side road out of East Hampton, 2.9 km and signed County Road 40. Runs north to the Three Mile Harbor marinas and then becomes Three Mile Harbor Hog Creek Road, which carries on up the east side of the harbour to Maidstone Park. It does not reach Cedar Point County Park — that is on the west side of the harbour, off Alewife Brook Road via Cedar Point Road.

  Source: openstreetmap.org

• Old Stone Highway

  Amagansett -> Springs (scenic alternate)

  Scenic alternate from Amagansett north into Springs — OSM still carries its old name, Amagansett-Springs Road. Narrow, winding, 6.4 km, posted 30 mph, passes through Accabonac Harbor wetlands and the Springs art community.

  Source: openstreetmap.org

• Napeague Meadow Road

  Napeague (north off Montauk Highway, across the meadows)

  A single 2 km road across the Napeague meadows and dune-grass flats, north of Montauk Highway. Useful for reaching the bay side and the harbour, but it is a spur, not a way around Route 27 — it does not continue to Montauk, and tidal flooding is possible at the ends.

  Source: openstreetmap.org

Ferries

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

• North Ferry

  Greenport (North Fork) <-> Shelter Island Heights · Crossing time not posted · North Ferry Company

  Drive-on, drive-off, and the operator's own schedule says North Ferry "operates every day of the year." Boats run every 8 to 15 minutes, and well outside daylight hours: first boats leave Shelter Island at 5:00am and 5:30am on weekdays (5:30am weekends) and Greenport at 5:15am and 5:45am (5:45am weekends); the last boat is 11:45pm from Shelter Island and midnight from Greenport, pushed to 12:45am and 1:00am on Fridays and Saturdays from Memorial Day through Labor Day. Autos $16.00 one way, $26.00 same-day return, plus $3.00 each for up to two extra passengers; foot passengers $3.00 each way, bicycles $4.00, motorcycles $8.00. Cash or checks only, paid onboard. Vehicles must be under 22 feet overall for the auto rate. There are no reservations — autos board first come, first served — and the schedule warns departures may be delayed by weather, traffic and ambulance stand-by. Greenport terminal is 305 Wiggins Street.

  Source: northferry.com

• South Ferry

  North Haven / Sag Harbor (400 Ferry Rd) <-> Shelter Island (135 South Ferry Rd) · Crossing time not posted · South Ferry Inc.

  Drive-on, drive-off, and the South Fork's link 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. The operator says ferries "operate continuously every 10-15 minutes" and run "365 days a year": Shelter Island departures 5:20am to 11:45pm Sunday–Thursday and to 1:45am Friday and Saturday; North Haven departures 5:30am to 11:50pm and to 1:50am. Fares are $18 one way and $25 round trip, cash only. Cars, trucks, buses, trailers, bicycles and motorcycles all cross, though large or commercial vehicles may be charged more. No reservations.

  Source: southferry.com

• Cross Sound Ferry

  Orient Point -> New London, Connecticut · Crossing time not posted · Cross Sound Ferry Services

  The only way off the East End by water without going through Manhattan: vehicles and passengers across Long Island Sound to New London. The operator's own booking categories are Vehicle and Passenger, Commercial / Truck / RV, and Vehicle with Trailer, and trips can be booked online in advance. A passenger-only high-speed boat, the SeaJet, runs seasonally on the same crossing. Orient Point (631) 323-2525, New London (860) 443-5281.

  Source: longislandferry.com

• Shelter Island freight (North Ferry trucks and commercial)

  Greenport <-> Shelter Island Heights — the North Ferry crossing · Crossing time not posted · North Ferry Company

  There is no separate freight ferry. North Ferry publishes no freight-only service or freight-only vessel; trucks, trailers and construction equipment cross on the regular boats under a published commercial tariff. Two-axle trucks $16.00 for the first 18 feet plus $1.29 for each additional foot; three or more axles $25.00 plus $1.29 a foot; construction trailers $2.00 a foot; loaded heavy dump trucks $12.00 plus $2.42 a foot overall; oversize or heavy loaded vehicles $94.00; school buses $94.00 one way and $128.00 round trip; empty hazardous materials $296.00 aboard the large ferry. Tide matters here: "very heavy vehicles with low clearance may have to wait for high tide" and "coach busses may not be able to cross at extreme high or low tides" — call the office before you drive down.

  Source: northferry.com

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, and the map data is no clearer than the signage: four separate roads carry Three Mile Harbor or Springs Fireplace in their names, and Three Mile Harbor Road simply changes name to Three Mile Harbor Hog Creek Road partway up, with no turn involved. Turning the wrong way puts you on the wrong side of the harbour. If GPS says 'turn right on Springs Fireplace' and you're already on Springs Fireplace, stop and look at a paper map.

  Source: openstreetmap.org

• Old Montauk Highway rejoins Route 27 at both ends

  Old Montauk Hwy leaves and rejoins Route 27 exactly twice: once at the west end out on the Napeague stretch, and once at the Montauk village end — not at Hither Hills, which is in the middle of the detour rather than at either end. Easy to overshoot the scenic entrance if you're not looking for it.

  Source: openstreetmap.org

• Mecox Road does not go to the beach

  A common misreading of the map, and the data settles it: Mecox Road runs 3.5 km east from Hayground and ends inland at a T-junction with Ocean Road, north of Mecox Bay. It is in Bridgehampton, not Water Mill, it does not dead-end, and it does not reach the ocean. It is Ocean Road, not Mecox Road, that carries on south toward the beach.

  Source: openstreetmap.org

• There is no Sagg Pond Road — but there are two Sagg Roads

  Sagaponack's confusable pair is not the one people expect. There is no Sagg Pond Road; the small residential turning is Sagg Pond Court. The real trap is Sagg Road, which is two different roads: the county-style road running north from Sagg Main Street toward Bridgehampton, and Sagaponack Road running west, which also answers to Sagg Road. Sagg Main Street is the one that goes to Sagg Main Beach.

  Source: openstreetmap.org

• The North Haven Bridge (Lance Cpl. Jordan Haerter Veterans' Memorial Bridge)

  The bridge from Sag Harbor to North Haven, leading to the South Ferry, carries Ferry Road (NY 114) and is two lanes — one each way, posted 30 mph, with no alternative crossing. Its official name is the Lance Corporal Jordan Haerter Veterans' Memorial Bridge, so signs and directions may use either. 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.

  Source: openstreetmap.org

Landmarks for wayfinding

Visible anchors you can orient from without opening a map.

• Sag Harbor Windmill (Wharf Street)

  Sag Harbor

  The small windmill by the water at the west end of the village waterfront — 8 Wharf Street, beside Windmill Beach and the approach to the North Haven bridge, not at the head of Long Wharf as it is often described. It houses the Chamber of Commerce visitor booth and carries the whale plaque the Chamber takes its logo from. The village navigates from it: 'two blocks back from the windmill.'

  Source: sagharborchamber.com

• Bridgehampton Commons

  Bridgehampton

  The shopping center on Route 27 that serves as the canonical "halfway between South Fork hamlets" landmark: if you can see the King Kullen sign from the highway, you are at Bridgehampton. King Kullen's own store locator lists Bridgehampton among the Long Island towns where it has a grocery store.

  Source: kingkullen.com

• East Hampton Village Green and Hook Mill

  East Hampton

  The Village's own history says Main Street was "laid out on the plain north of Hook Pond" and served as the common in the original 1648 settlement — which is why every direction given in the village is given relative to it. The Village calls the windmill at the north end Hook Mill, not "Hook Windmill"; it is one of three structures, with the Gardiner Windmill and Home Sweet Home, given a historically accurate restoration under the Village's historic-services program.

  Source: easthamptonvillage.gov

• Maidstone Club

  East Hampton

  The private golf club on the ocean side of East Hampton, off Further Lane. A useful marker, but not the one it is often taken for: it sits about 1.3 km south of Route 27 rather than on it, and the village boundary continues roughly 1.6 km east of the club, so passing it does not mean you have left the village.

  Source: openstreetmap.org

• Shinnecock Canal Bridge

  Hampton Bays

  Route 27 crosses the Shinnecock Canal here, and locally the canal is the dividing line between "the Hamptons" and "up-island." It is not, however, a town line: Hampton Bays sits inside the Town of Southampton — the Town runs the Hampton Bays Water District and the Hampton Bays parks — so both banks of the canal are Town of Southampton.

  Source: southamptontownny.gov

• Hither Hills State Park entrance

  Montauk

  State Parks gives the park's address as 2 Old Montauk Highway, Montauk, and the entrance is off Old Montauk Highway. Behind it is a 189-site oceanside campground with a swimming beach, hiking and nature trails, a playground, playing fields, showers, food service and year-round fishing; the "walking dunes" of Napeague Harbor are inside the park. A mental waypoint more reliable than GPS in the Montauk dropout zone.

  Source: parks.ny.gov

• Montauk Point Lighthouse

  Montauk

  The literal end of the road — Route 27 runs out here. The parking lot is Montauk Point State Park, 2000 Montauk Highway, and it is not free: State Parks collects an $8 vehicle entrance fee ($35 for buses) from 8:00am to 4:00pm in season. State Parks describes the park as neighboring the Montauk Lighthouse, "the oldest lighthouse in New York State, commissioned by President George Washington in 1792," rather than containing it — so the park fee is not lighthouse admission.

  Source: parks.ny.gov

• Greenport Mitchell Park and Carousel

  Greenport

  The waterfront park at the center of Greenport village. The carousel stands in the Jess Owen Carousel House; the Village says it is 100 years old and was gifted from Grumman Aircraft Corp. Rides are $3.00, or $30.00 for a 15-ticket book. Open daily in season — Sunday to Friday 11am–7pm and Saturday 11am–8pm through Labor Day weekend — then weekends 11am–5pm off season, with the last ride 15 minutes before closing and closures on Thanksgiving, Christmas and Easter Sunday. Orient yourself here: Front Street is two blocks inland and North Ferry to Shelter Island leaves a short walk west. Cross Sound Ferry does not sail from Greenport — it leaves from Orient Point, at the far east end of Route 25.

  Source: villageofgreenport.gov

Cell signal dead zones

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

• Montauk and the foot of Hither Hills

  Montauk was one of four areas East Hampton Town's coverage mapping found where signals do not reach in any usable form, and the western foot of Hither Hills is the worst of it — EMS reported no communication at all at Gurney's. Towers have gone in since, so cache offline maps before you leave Amagansett.

  Source: 27east.com

• Napeague stretch (Amagansett to Montauk)

  Thin rather than empty: the small cells along the stretch have carried a single carrier, so service here depends on which network you are on. Seven more were mapped for Napeague in the build that began in 2025. Pre-load the route — turn-by-turn still hangs over the open meadows.

  Source: 27east.com

• Springs

  Springs and Northwest showed the biggest gaps on every map the town's consultants produced. Three more monopoles are called for here on top of the 180-foot tower at Camp Blue Bay, and Springs is a main target of the small-cell build that began in 2025.

  Source: 27east.com

• Northwest Woods and Northwest Harbor

  One of the two worst gaps in the town's mapping, and tree cover is why — a small cell reaches three-quarters of a mile at best, less through dense woods. Most of the 189 nodes in the build that began in 2025 are aimed here and at East Hampton North.

  Source: 27east.com

• Wainscott

  The fourth hamlet the town's study found with no usable signal in places. Ten small cells were mapped for Wainscott in the 2025 build, and consultants want a further 100-foot tower toward the eastern side of Georgica Pond.

  Source: 27east.com

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 — Seaplane and small-aircraft charter

   Who: Anyone willing to request a charter quote from Tailwind or Shoreline

   Access: Manhattan ↔ Sag Harbor / East Hampton water. Charter quote only — no operator currently publishes a per-seat Manhattan-to-Hamptons fare. 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