In America, where cars are king and the hero’s journey is usually a road trip, long-distance train travel remains the realm of romantics — the sort who look down empty tracks and wonder where those rails could take them.
Admittedly, the Long Island Rail Road’s 7:47 a.m. service to Ronkonkoma isn’t typically the stuff of travel fantasies. But on a recent Sunday morning, I was buzzing with anticipation as that train slipped out of Penn Station, launching me on a journey I’d been daydreaming about for years.
Over the next four days, I’d be attempting a whistle-stop tour of the Northeast entirely without driving, instead following a carefully plotted-out itinerary of trains, buses and ferries. One missed connection could also imperil the entire odyssey, leaving me vulnerable to obstacles that were, if not exactly Homeric, extremely inconvenient — trains that run only once a day, peak-season New England hotel pricing and, worse, the siren song of the Uber app.
Still, it was hard not to smile as the 7:47 sped me toward all the summertime pleasures of southern New England, its beaches, bivalves and bike trails laid out across the map like a well-set picnic table.
As long as I made my next train.
New York City to Greenport, N.Y.
Vineyards, Ospreys and Oysters
I planned to spend my first night on Block Island, a tiny summer haven about 125 miles away from Manhattan — and to get there by direct ferry from Long Island’s pastoral North Fork, treating myself to a lunchtime layover in the former whaling town of Greenport.
Naturally, the transportation gods had other plans. That ferry was canceled for the weekend because of mechanical issues, which meant my 75-minute straight shot to Block Island would be a two-boat, three-hour voyage via New London, Conn.
Undeterred, I pressed forward, changing trains at Ronkonkoma to the diminutive, diesel-powered Greenport Scoot ($24.50 for the full three-hour trip from Penn Station). We trundled east at 40 miles per hour past vineyards, horses and nesting ospreys, the only train on this lonely stretch of single track. (In the 1840s, before the present-day Northeast Corridor tracks were laid through southeastern Connecticut, this train line was actually part of the quickest route from New York to Boston.)
I learned this at Greenport’s railroad museum ($9), housed in the station’s old freight house. The tracks dead-end just shy of the water’s edge, and I happily breathed in the sea air as I strolled into town.
With about three hours to explore, I picked up an iced latte ($4.75) from Aldo’s Coffee Company and then promptly got lost in the shelves at Burton’s Bookstore, a few doors down, before heading to Little Creek Oysters for some sensational local seafood: Mexican-inspired raw oysters, with ponzu and hot sauce ($28), and a super-fresh tuna tostada ($18).
Greenport to Block Island
On the Sparkling Sea
The No. 92 bus to Orient Point ($2.25) pulled up just late enough to make me start to sweat, but soon we were flying down the road toward the ferry terminal.
For locals, the Cross Sound Ferry is simply a convenient way to avoid hours of highway driving on I-95 and the Long Island Expressway, but I was smitten from the moment the Susan Anne blasted its horn and pulled away from shore. Finding a spot on the upper deck, I cracked open my book, basking in the sunshine as we passed bobbing fishing boats and lighthouses perched on lonely islands.
After a quick transfer in New London onto the Block Island Express ($38 total for both ferries), I was back on the water, munching on a hot pretzel ($5) from the onboard snack bar — and about an hour later, we were docking in New Shoreham, Block Island’s picturesque (and only) town. My room at the newly renovated Eureka Hotel ($276) was a 10-minute walk from the pier, and once I’d checked in, I headed to dinner (fish tacos and a spicy frozen margarita for $35 at Los Gatitos) and a show: first a beautiful sunset, then a solid cover band at Captain Nick’s Rock-n-Roll Bar, just the kind of eclectic, inviting dive bar you’d hope to find on an island in the Atlantic.
Block Island to Narragansett, R.I.
Wild Things and Waffle Cones
The island’s serenity took a surreal turn the next morning: I had already walked past three kangaroos, four alpacas and a half-zebra-half-donkey before sitting down to breakfast and being offered a tray of edible flowers.
The Eureka is the latest addition to the island’s family-owned 1661 Resort Collection, and the path to the main inn’s restaurant took me through their impressive gardens and animal sanctuary. After my hearty — and surprisingly floral — breakfast ($16), I checked out, stored my bag and rented a moped ($96 from Aldo’s Mopeds). I spent two gleeful hours zooming around the island, admiring the cedar-shingled architecture and the 200-foot-tall cliffs at Mohegan Bluffs.
Before leaving the island, I refueled with two local classics — clam cakes from Rebecca’s Seafood ($9.25) and a Del’s lemonade ($7) — before catching the 3:30 p.m. high-speed ferry, a 30-minute windblown ride to Point Judith, R.I. ($29). We pulled in as the traditional ferry (which takes twice as long) was unloading hundreds of riders, but back on land, I was the only passenger from either boat catching the 4:19 p.m. Rhode Island Public Transit Authority No. 69 bus ($2) into the center of Narragansett.
It was a perfect beach day, and for a second, I considered hopping off the bus at Scarborough State Beach. But I knew the next bus wouldn’t come until 6:15, and I had a dinner reservation to make. So I stayed on board until we reached the charming village of Wakefield, where I’d booked an Airbnb for the night.
Ninety minutes later, I rode the No. 69 back a few stops to the upscale Matunuck Atelier, a restaurant that surely sees very few diners arrive by bus. The lobster-vanilla dumplings ($14) stole the show, rivaled only by the ice cream down the street at Brickley’s, where the wafting smell of freshly made waffle cones stopped me in my tracks on my 20-minute walk home.
Wakefield to Pittsfield, Mass.
Heading for the Hills
The next morning, armed with a still-warm morning bun ($5.85) from the South County Bread Company, I caught the 7:40 a.m. bus to the Kingston train station (a 30-minute ride) and began my Amtrak trek to the Berkshires: first the Northeast Regional to Boston ($30), then a four-hour ride to Pittsfield on the daily Chicago-bound Lake Shore Limited ($40), currently the only way to cross Massachusetts by train.
Stretching out in my spacious “roomette” sleeping compartment (well worth the $68 upgrade), I tucked into a sublime chicken-salad sub ($13) from Al’s Cafe near South Station and savored the view through the oversize window — particularly as we started winding into the Berkshire foothills and the horn echoed through the hamlet of Hinsdale, where I’d spent so many summers at camp listening for this same train.
Pittsfield looked regal in the late-afternoon sun, its wide, sleepy streets belying the fact that there were two stage productions in town that night. But after checking into the attractive Hotel on North ($284) and enjoying some delicious dolma and falafel at the nearby Sofra Turkish Mediterranean Grill ($28), I opted for a different sort of theater, heading to a lively Mexican watering hole called Tito’s for the Mexico-Ecuador World Cup match.
Pittsfield to New York City
Slogging Into the Sunset
I had grand designs to spend a day exploring the artsy towns of Lenox, Lee and Stockbridge using the Berkshires’ extensive, free regional bus network. But again, the transportation gods had other plans. The route I had been eyeing was canceled all day — not enough drivers, the man at the customer service window said.
So I rented an e-bike from Berkshire Bike & Board ($90 for the day) and hit the 13-mile Ashuwillticook Rail Trail. Riding under a lush tree canopy and along shimmering Cheshire Reservoir may have been an even better antidote to the 90-degree heat than an air-conditioned bus.
Recharged by a chicken torta and fried plantains ($19) from Placita Latina, a Salvadoran-Mexican restaurant in Pittsfield, I made my way back to the train station to wait for that day’s Lake Shore Limited. If it had been Friday or Sunday, I could have taken the Berkshire Flyer straight to New York, but because it was Wednesday, I had to connect at Albany-Rensselaer to Amtrak’s Adirondack train coming from Montreal ($71 for the whole two-train, five-and-a-half-hour slog). Nonetheless, I was looking forward to a sunset ride down the Hudson River.
And the ride was a delight — until Poughkeepsie, where the conductor sighed before announcing that an incident down the line meant we would be delayed indefinitely.
Did my two-and-a-half-hour train from Albany ultimately chug into Penn Station two and a half hours late? Yes it did.
Would I do it all again next week? Absolutely.
Follow New York Times Travel on Instagram and sign up for our Travel Dispatch newsletter to get expert tips on traveling smarter and inspiration for your next vacation. Dreaming up a future getaway or just armchair traveling? Check out our 52 Places to Go in 2026.
The post No Car? No Problem: An East Coast Odyssey by Train, Ferry and Bus appeared first on New York Times.
