Trip 46 — Long Island Walk

Day 10: Sag Harbor to Montauk
Saturday, 15 November 2025

Yesterday: 52963 steps/41.14 km/25.56 mi/7h 4m
Total: 465914 steps/362.20 km/225.06 mi/63h 0m

Liz and I revisit our PEI arrangement: She conducts the day's therapy sessions while I walk, and we meet up at the end. It's bright and sunny, and the empty marina opposite the Sag Harbor Inn looks ready and hopeful for action that won't happen for some months.

I walk through town, past the large windmill and the businesses that are preparing for the day: Schiavoni's Market, the American Hotel, a liquor store and a bakery, the giant Art Deco letters of the Sag Harbor Cinema. On the way out of town, a marker identifies the location of the former toll gate. Until 1899, it cost four cents for a cart or wagon with one horse to travel between Sag Harbor and East Hampton, and "about eight cents" with two horses.

I'm soon taking a staircase pattern of lefts and rights through the back roads to East Hampton. They're as quiet as their names suggest: Swamp Road, Two Holes of Water Road, Stephen Hands Path, Cedar Street. Having almost touched East Hampton, I bounce back up toward Springs on Accabonac Road, Red Dirt Road, and Old Stone Highway.

There's very little traffic; this serenity is what I'd expected on the terrible Noyack Road back in Southampton. There's a sameness to the roads: the same bare trees, the same crackle of leaves underfoot, houses set so far back from the road that only their driveways reveal their existence. A deer crosses in front of me, unafraid.

Vicky Wolf Ruby is the only place for lunch. Also called the Old Stone Market, it's set in an old, wooden house. It's part general store and part takeout counter, but they have three stools inside and picnic tables outside. The offerings lean toward Cuban and Greek, revealing the owners' and staff's heritages; there are empanadas alongside the spanakopites.

The lunch specials include corn chowder and the store-proclaimed "best Cuban ever." When I ask for the soup, she comes to the customer side and takes a plastic container out of the fridge. She brings it to the back to heat it up, but then she returns.

"There's something wrong with it," she says. "It doesn't smell right. Do you want chicken-vegetable soup? I just made it. Fresh. Hot. You'll love it."

While she ladles me some of the new soup, her coworker discards the remaining containers of chowder. I make two trips to bring my lunch to the back: the soup, a Cuban sandwich, a bottle of black-cherry soda, and a peanut-butter cookie, along with a bottle of locally made peach hot sauce to bring home. I wedge myself onto a stool amid the bottles of Poland Spring, near packages of Doritos and bottles of Greek olive oil. The soup is excellent and perfect for the chilly day, with large chicken cubes and pieces of celery and carrot, and the Cuban is overflowing with so much tasty meat that I finish only half of it.

Then it's back to Albert's Landing Road (with and without the apostrophe), Fresh Pond Road, Cross Highway to Devon (leading to the Devon Yacht Club), Abraham's Landing Road, Bendigo Road, and Promised Land Road — suggesting a kind of biblical frontier as I approach the Napeague Bay and traverse a section of the Napeague State Park.

Promised Land Road seems to have most of its houses for sale. Some of them are still going up; others are of the vintage-look variety, and some are that modern, boxy design with giant windows, solar panels, and all sorts of electronic conveniences. They go for $2.5 million to $5 million.

Napeague Meadow Road crosses a few tiny streams on the approach to the Montauk Highway. The trees are gone; there's just a grassy marsh, with the bay in the distance. Before I complete the final steps to the highway, my progress is paused while the Long Island Rail Road makes its way from Amagansett to Montauk — a stunning coincidence, since only nine eastbound trains serve the railroad's easternmost terminus on Fridays (and only five on winter weekend days).

I'm on Route 27, Montauk Highway, for the first time in a decade. The traffic is fast but sparse, and they've turned the wide shoulder into a bike lane. Across the highway is the iconic "Lunch" sign designating the Lobster Roll restaurant, and on my side is the Clam Bar, both closed for the season. This is the only road connection between East Hampton and Montauk, the little strip of land called Napeague.

At Hither Hills State Park the land bulges out again to the north, and I turn left onto one of the park roads. It's dirt, not much more than a trail, and I'm only slightly concerned about signage indicating that the hunting season has begun. The trail swerves to the right and runs parallel to the Long Island Rail Road track for the next hour and a half. The train comes back west through the woods, and one capable car passes me on the bumpy road.

It's also a very hilly trail, with occasional puddles left over from last week's rain. Narrow trails branch off for mountain biking. The hunting area ends, and I'm alone until the trail dumps me out into an industrial area. Slow-moving trucks negotiate around me to find their resting spots for the day.

I hurry up Flamingo Avenue just in time to meet Liz coming down the platform at Montauk's lonely train terminus. The train ride out here is beautiful but long — it takes three hours from Manhattan — and the tiny station at Amagansett, hidden down a driveway, already feels like the end of the earth. And then it's another 20 minutes through the park to Montauk.

The train ride ends unceremoniously at the little Montauk station hut, next to the unassuming Flamingo Avenue. It's a 25-minute walk into town. I used to come out here a few times a year, but I've never had the opportunity to stay in the middle of things. The Royal Atlantic Beach Resort — not as grand as it sounds — has only three cars in its lot, but it'll fill up at night.

We celebrate our arrival at the Shagwong, the landmark tavern with its sign "Piano player wanted — Must have knowledge of opening clams." The prices are twice what I remember (it has been ten years), but it's still friendly and one of the main gathering spots for residents. At nine, a keyboardist comes in and takes requests for sing-along karaoke (I don't know about his shucking ability). Longtime Long Island resident Billy Joel is a favorite, and we get "Vienna" twice.

Today is the last resting day of the Abecedarian Walks, and Montauk is a good place to chill. It's got a bookstore, tacky souvenir shops, a couple of liquor stores, a place for fudge, and a brewery outlet. Above all, it has a sandy beach, and today it's sunny and reasonably warm for mid-November. There are a few people with their dogs, and a cigar smoker is feeding the seagulls.

We eat our way around, starting with the place I remember as John's Pancake House. According to the menu, it's officially Mr. John's Pancake and Steak House, perhaps the only steakhouse in the world that closes at 2 p.m. They've finally started taking credit cards this year, and while they impose the annoying surcharge and tips still have to be in cash, it's a step in the right direction.

After a lazy afternoon we have a snack at Streetfood on the Green — an unlikely name for a pan-Asian restaurant — and, when it's time, dinner at Tauk at Trail's End, beckoned by the neon diner-style lettering and the promise of live music until 9 p.m. The interior is at odds with the signs, however. It's more upscale, and we're the only customers, wondering whether 8:15 is too late for a meal.

We're welcomed, and we share raw Montauk clams, crab cakes, spicy raw tuna on a plate of wontons, and lobster with linguine and red sauce. As for the music, we're puzzled. In his dreadlocks, he's not quite singer, not quite keyboardist, and not quite DJ. He plays reggae and soul, he never touches the keyboard, and he dances with his back to us, in his own world. He sometimes reads lyrics from a phone, not quite speaking or singing them, more like chanting. When he tires of a song, he cuts it off and skips to the next one.

I'm not sure whether he's performing. I'm not sure whether he thinks he's performing. But he's having a good time, and what matters beyond that?

Go on to day 11