The LIRR
Montauk is the end of the line
Trains leave from Penn Station, Grand Central and Hunterspoint Avenue. Almost all trips require a transfer at Jamaica, and east of Babylon the electric third rail ends — the rest of the run is diesel, on a much thinner timetable. That is the single most important fact about taking the train here. On a weekday in February there may be only a handful of trains all day.
In summer the LIRR adds seasonal service, including a reserved-seat Friday express that skips most of the stops. It sells out. If you want it, buy it the moment tickets open.
Montauk station sits at the edge of the village. You can walk from the platform to most village lodging in under fifteen minutes, and to dinner in less.
Check the timetable first, not lastDo not book lodging and then look up trains. The eastern end of the branch runs a schedule that will decide your arrival and departure days for you.
The Hampton Jitney
A coach, not a bus
The Montauk line picks up on the East Side of Manhattan and runs straight through, no transfer. Seats are reserved, there's a bathroom and wifi, and someone comes through with a snack. It is a civilized way to travel and it is genuinely popular with people who could afford to do otherwise.
The catch is structural: the Jitney drives Route 27 like everyone else. On a Friday in July it will be late, and there is nothing the driver can do about it. Book the earliest departure you can stomach.
Driving
The Long Island Expressway to Route 27
The standard route is the LIE east to its far exits, then across to Sunrise Highway (NY 27), which narrows and becomes Montauk Highway as it enters the Hamptons. From there it is one road, and in three places — the Shinnecock Canal, Southampton village and Bridgehampton — it drops to a single lane in each direction with traffic lights. Those three places are where the four-hour Fridays come from.
Locals call the weekday morning eastbound crawl of contractors and landscapers the Trade Parade. It is real, it starts early, and it is why a 7am departure is not as clever as it sounds in summer.
Once you're past Amagansett the road opens up, the trees give way to dunes, and the last ten minutes are the best of the drive. Take Old Montauk Highway for that final stretch rather than staying on 27 — it rolls along the bluff above the ocean and adds about four minutes.
Parking is the second problemMany Montauk beach lots require a Town of East Hampton permit in season, and non-resident permits are limited. Confirm what your lodging provides before you assume you can park at the beach you picked.
Ferries
From New England, seasonally
If you're coming from Connecticut or Rhode Island, a ferry can save you the entire length of Long Island. Seasonal passenger service has historically run between Montauk and both New London and Block Island, and vehicle ferries cross to Orient Point on the North Fork — though from Orient you still face a long drive around the bays.
All of it is seasonal, weather-dependent, and subject to change year to year. Confirm the operator's current schedule directly rather than trusting a page like this one.
Flying
Nothing lands in Montauk
The nearest commercial airports are Long Island MacArthur in Islip, which is closer than it looks and badly underused by visitors, and JFK, which is bigger but roughly two and a half hours away without traffic. East Hampton Airport is the nearest general-aviation field; its operating rules have been contested and revised repeatedly in recent years, so check current status before planning around it.
There is no scenario in which flying is the relaxed option. Take the train.