New York is unusually well placed for days out. Two commuter railroads and Amtrak reach a long way in a short time, and a lot of what they reach is genuinely different from the city rather than more of the same. Every trip below is doable and returnable in a day without a car.
1. Cold Spring and the Hudson Highlands
Metro-North Hudson Line from Grand Central, about 80 minutes.
The single best day trip from New York, and the one that most surprises people who assume you need a car. The train runs along the eastern bank of the Hudson the whole way, which is one of the most scenic commuter rides in America, and drops you in a village of nineteenth-century buildings at the foot of the Highlands.
Breakneck Ridge is a short, steep, genuinely scrambling hike with views up and down the river; the trailhead has its own request-stop station on the same line. Little Stony Point is easier and mostly flat along the water. Main Street in Cold Spring is antique shops, a bookshop and half a dozen good places to eat.
Go on a weekday if you can. On an October Saturday the trains and the trail are both full.
2. Beacon and Dia
Metro-North Hudson Line, about 90 minutes.
Dia Beacon is a former Nabisco box-printing factory of 300,000 square feet, converted into a museum of large-scale minimalist and conceptual art lit almost entirely by daylight through the sawtooth roof. Richard Serra, Donald Judd, Louise Bourgeois, Dan Flavin, Agnes Martin. It is one of the great art spaces anywhere and it is a ten-minute walk from the station.
Main Street in Beacon has a strong food and shop scene, and Mount Beacon rises directly behind the town.
3. Storm King Art Center
Metro-North to Beacon then a seasonal shuttle bus, or a coach from Port Authority. Around two hours.
Five hundred acres of hillside and meadow with monumental outdoor sculpture — Calder, Serra, Goldsworthy, di Suvero, Maya Lin’s earthwork Storm King Wavefield. It is open roughly April to November, tickets are timed and booked in advance, and it is worth the awkwardness of getting there.
Take a bicycle or hire one on site; the site is far bigger than it looks from the entrance.
4. Philadelphia
Amtrak from Penn Station, about 75 minutes. NJ Transit plus SEPTA, about two and a half hours and a third of the price.
An entire second city, and a very good one. Independence Hall and the Liberty Bell, the Philadelphia Museum of Art with the Rocky steps, the Barnes Foundation — one of the strangest and best private collections in the world — Reading Terminal Market, and the Italian Market.
Amtrak’s Northeast Regional is comfortable and expensive; booking two or three weeks out roughly halves the fare. The NJ Transit route involves a change at Trenton and is the budget option.
5. The Rockaways
A train to Broad Channel then the S shuttle, or the NYC Ferry from Wall Street. About an hour and a quarter.
Still New York City — it is in Queens — but it is a proper Atlantic beach with surf, a boardwalk, and a food scene that has grown up around it. The ferry from Manhattan is the nicer approach and costs a standard fare.
Free, in the sense that a beach is free.
6. Sleepy Hollow and Tarrytown
Metro-North Hudson Line, about 45 minutes.
Washington Irving’s house at Sunnyside, the Gothic Lyndhurst mansion, and the Old Dutch Church and burying ground where Irving himself is buried along with Andrew Carnegie and Walter Chrysler. The Kykuit Rockefeller estate runs tours from Philipsburg Manor.
In October the whole area leans hard into the Headless Horseman and the events sell out weeks ahead.
7. New Haven
Metro-North New Haven Line, about two hours, or Amtrak in 90 minutes.
Yale, which means the Yale University Art Gallery — free, and extraordinary — and the Yale Center for British Art, also free, in a Louis Kahn building. The Beinecke Rare Book Library has walls of translucent marble that glow, and a Gutenberg Bible.
New Haven pizza is a serious local tradition and Wooster Street is where it lives.
8. Fire Island
LIRR from Penn Station to Bay Shore, Sayville or Patchogue, then a ferry. Two to two and a half hours.
A thirty-mile barrier island with no cars at all, reached only by boat. The communities are distinct — Cherry Grove and the Pines are historic gay resorts, Ocean Beach is the busiest, Sailors Haven and the Sunken Forest are National Seashore.
Summer only in any real sense, and it is a long day. Worth it for the strangeness of a place forty miles from Manhattan where a wheelbarrow is the standard vehicle.
Practical notes
Metro-North leaves from Grand Central. LIRR leaves from Penn Station and Grand Central Madison. NJ Transit and Amtrak leave from Penn Station and Moynihan Train Hall. None of them accept an OMNY tap; buy tickets on the relevant app before boarding, because on-board fares carry a penalty.
Off-peak fares are substantially cheaper on Metro-North and the LIRR and apply to most trains outside the weekday commuter rushes.
Autumn is the reason to do the Hudson Valley trips, roughly mid-October. Summer weekends on any of these routes are busy.