Riding the Cannonball: the LIRR's reserved summer express to the East End

The Cannonball is the fastest scheduled public passage from Manhattan to the East End, and for several decades it has carried a reputation out of proportion to the number of trains involved. It is a single eastbound run, on two days a week, for one part of the year. Most riders who reach the Hamptons by Long Island Rail Road never board it. Those who do tend to plan their summer Fridays around it.

What the Cannonball is

The Cannonball is a seasonal reserved-seat express operated by the Long Island Rail Road over its Montauk Branch. It runs only in the warm months — the 2026 edition returned to service in the third week of May — and only on Thursdays and Fridays, the two afternoons when eastbound demand is heaviest. The train departs Penn Station in mid-afternoon, around 4:06 PM, and runs express across Long Island before reaching the resort towns.

What distinguishes it from an ordinary Montauk Branch train is twofold. First, it does not make the usual procession of intermediate stops; it skips the Babylon and Jamaica changes that define most eastbound trips. Second, a block of cars on the train is sold as reserved Hamptons-bound seating, so a paying passenger has an assigned place rather than a scramble for one. The combination of express routing and a guaranteed seat is the whole point.

The route, in order

After leaving Penn Station the Cannonball runs without Hamptons-relevant stops until it reaches the East End, where it serves, in sequence:

• Westhampton — the first stop, reached in roughly 92 to 96 minutes from the city
• Southampton
• Bridgehampton
• East Hampton
• Montauk — the end of the line

That ninety-minute figure to Westhampton is the number worth holding onto. On a summer Friday a black car or a self-driven rental can spend longer than that simply crossing the Shinnecock Canal in Hampton Bays. The train, running on its own right-of-way, is indifferent to the NY-27 backup that decides every road-bound passage.

Fare and reservations

A Cannonball seat is inexpensive by the standards of the corridor. The fare in the 2026 season is about $33 one way to the East End zone — more than a standard off-peak LIRR ticket but a fraction of what a coach line’s premium tier or a flight will cost. The trade is that the seat is finite and reserved, so it must be bought in advance through the railroad’s ticketing app or at a Penn Station ticket office or machine. The reserved cars sell out earliest on the worst-traffic Fridays, which is precisely when they are most valuable.

A connection from the Grand Central Madison terminal exists for riders who would rather not start at Penn, but the Cannonball itself originates at Penn Station, and the simplest way to ride it is to be on the platform there in the early afternoon.

Why people build a Friday around it

The Cannonball solves a specific problem: the fixed-arrival summer Friday. If a traveler has a dinner reservation in East Hampton or a houseguest obligation in Bridgehampton and must leave Manhattan during the early-afternoon window when the road begins to seize, the train is the cleanest insulated option short of flying. It cannot be delayed by a jackknifed truck on the expressway or by beach traffic on Montauk Highway, because it touches neither.

The cost of that certainty is rigidity. There is one Cannonball each running day, at one time. A traveler who misses it falls back to the ordinary Montauk Branch service — slower, with a change at Jamaica or Babylon, and no guaranteed seat. The train rewards planning and punishes improvisation, which is the opposite of the road’s temperament.

A note on the off days

Even within the season the Cannonball does not run every Thursday and Friday without exception. Holiday-adjacent dates can shift or suspend the service, and the railroad publishes the season’s calendar of running days in advance. A rider counting on a particular Friday should confirm that day appears on the timetable rather than assume the pattern holds straight through the summer.

Where it sits among the passages

Against the other ways east, the Cannonball occupies a narrow and useful niche. It is far cheaper than a helicopter or seaplane and far more weather-reliable. It is faster and more road-proof than any coach line, including the premium ones, because it leaves the highway entirely. Its weaknesses are its scarcity — two days a week, one departure — and its origin at Penn rather than at a rider’s doorstep. For a traveler whose schedule fits the timetable, it is arguably the best-value passage in this almanac. For one whose schedule does not, it is simply unavailable, and the choice reverts to the road or the air.

Frequently asked questions

Which days does the Cannonball run? During the summer season it runs on Thursdays and Fridays only, with one afternoon departure from Penn Station, subject to a published calendar that omits certain holiday-adjacent dates.

How long does it take to reach the Hamptons? About 92 to 96 minutes from Penn Station to Westhampton, the first East End stop, with Southampton, Bridgehampton, East Hampton, and Montauk following.

How much is a ticket and do I need to reserve? The 2026 fare is roughly $33 one way to the East End zone. Because seating in the reserved cars is finite, tickets should be purchased in advance through the railroad’s app or at Penn Station.

Does the Cannonball avoid Hamptons traffic? Yes. It runs on the railroad’s own track and never touches NY-27, so it is unaffected by the summer-Friday backup at the Shinnecock Canal that delays every road passage.