Trip 46 — Long Island Walk

Day 7: Around Orient Point and to Jamesport
Tuesday, 11 November 2025

Today: 73523 steps/57.18 km/35.53 mi/9h 49m
Total: 343962 steps/267.64 km/166.30 mi/46h 26m

They've talked up the cold and the wind, and I'm not taking any chances. I have two clean T-shirts, and I put them both on, along with my thick long-sleeve shirt and my fuzzy, warm, hooded jacket. Everything is dry after yesterday's soaking, having hung in front of a blasting heater all night.

Today's long segment is in two roughly equal parts: the loop around Orient Point and back to Greenport and the walk along the southern side of the North Fork to Jamesport. Checkout at the Townsend Manor Inn is at 11, but I've arranged to leave my packed bag in my room until noon so I can avoid carrying it for the first half.

I nervously open the front door, expecting the kind of frigid attack that makes you shiver and freeze like a cartoon character hit by lightning. It's not as painful as I expected. It's chilly, but with all those tops on and my hood up, I'm comfortable.

I proceed up Main Street. Near the traffic circle, workers are putting up warning posts as they start their day. I weave my way through and thank them for making space.

Turning right puts me on Main Road, the continuation of Middle Road and, earlier, Sound Avenue. After a short distance I'm in East Marion, where I'm delighted to have a sidewalk that runs the length of the community. There's another in the hamlet of Orient, just ahead.

In between is a causeway separating the Long Island Sound and Orient Harbor. The wind kicks up here, and the power lines rattle. It's a partly sunny day, an hour after sunrise, and to my right the sun is casting a lampshade pattern of rays through the clouds. I can just make out the South Fork and, closer and to the southwest, Shelter Island.

Orient feels like a last frontier. It's way beyond the railway terminus at Greenport, although the S92 bus runs reasonably frequently between the Orient Point ferry terminal and East Hampton on the South Fork. A white church in Orient, built in 1843, houses a congregation that's been active since 1717. The traffic picks up approaching me: The ferry must have just come in.

A boy and his black dog are in the driveway next to a shingled house, formerly a tavern, built in 1656. There's one more produce stand, and in front of various houses are signs advertising honey, chicken and duck eggs, and raw oysters, the last to be paid for on the honor system using the slot in the adjacent lockbox. Down a side street are the post office, a country store, and a cafe.

It's yet another hour to Orient Point, where I arrive just in time to see the 9:00 ferry depart for New London, Connecticut. At this time of year, it runs about once an hour (but not overnight) and takes 40 to 80 minutes, depending on whether it's a high-speed service. Discussions of building a bridge to Connecticut here have gone on for decades but not advanced beyond that.

It smells of the salty sea, and the sandy beach is littered with shells. A trail takes me through a grassy area and to the absolute tip of the North Fork, where I climb down some rocks and greet a fisherman. The other creatures here are a few hundred gulls, who make a go-around upon seeing me but then settle back onto the pebbles. They might technically be closer to the real tip than I (some might say the hypertip), but I let that be their domain and don't want to disturb them.

Instead, I admire the view of Plum Island just ahead, past a small lighthouse. To the north, across the sound, I can just make out Connecticut. This really is quite far east; due north is Lyme, and I can still make out the ferry, getting smaller as it proceeds northeast to New London. Meanwhile, the Long Island–bound ferry has pulled in, and when I finish the loop around the tip, the cars — and here's where some of the trucks came from — are heading toward Greenport.

It's a long, blustery 2¼ hours back to Greenport, where I pick up my bag and head down Main Street. I have lunch at the Crazy Beans diner, continuing the sweet-savory theme with their pancake quesadilla: sausage, bacon, scrambled eggs, and cheese between pancakes. With hot sauce and syrup, naturally.

The wind has gotten fierce, and there have been a couple of snow flurries. I've gone 29 kilometers and have 28 remaining. I don't feel like going another fine hours, but that's the schedule, and the sooner I start, the more I can accomplish in daylight.

I loop around the waterfront — was it here where I learned to shuck oysters? — and past the little train platform, next to which are the Shelter Island ferries and, on the other side, a fascinating museum of the Long Island Rail Road that I visited years ago.

I make my way back to Main Road. The sidewalk ends, but a wide shoulder remains. After a couple of kilometers I see a mailbox for house number 69700. My destination is 1399. It's going to be a long afternoon.

And, at times, a tough one. There are brief moments of wind and snow: the kind of beady snow that blows at you and stings. It's better than rain — at least it won't get my coat soggy — but it's sometimes difficult walking.

The Country View farm stand is open, and I pick up a slice of cinnamon crumble. Every couple of kilometers I give myself a small treat.

After the attractive village of Southold, the road turns sharply to the left, and I'm back on the wine trail. I must pass 20 wineries: Duck Walk (which I've visited before), Osprey's Dominion, Lenz, Pindar, Bedell, Pugliese, many others. Somewhere around Duck Walk I notice that a sidewalk has begun on the right. I cross over, and I'm delighted to find that it's continuous for an hour to Cutchogue, where it abruptly ends in front of a white fence next to a driveway.

But it starts again when I reach Mattituck, where I almost stop for another snack; the Love Lane Kitchen is just up the block, and if it were open I might pop in for another hot chocolate. I'm handling long distances better than I did five years ago, but the prospect of another seven kilometers is daunting, especially as it's gotten dark.

If the sidewalk past the wineries surprised me, the one past Mattituck absolutely astounds me, taking me all the way to Jamesport. I still have to be careful: there are leaves on the surface, frost on the grass, and tree branches blown into my path. Occasionally I need my phone's flashlight. It's cold, but I barely notice.

I check in to the Shoresomething Inn motel (it's Shorewood, but I keep wanting to say Shoreham or Shoreview) and crank up the heat to 74. It's a noisy machine, like a hair dryer (or those useless bathroom hand dryers), and the air it blasts starts out cool every time it restarts. But it does the trick.

I manage to retrace my path 600 meters to Cliff's Elbow Room, where I arrive at 7:48 and barely make the kitchen's cutoff time. While I enjoy mussels and a half-duck in a sticky-sweet merlot sauce, the bartender chats with customers about their Thanksgiving family plans. Of paramount importance, she says, is the establishment of a "coping corner" — essentially a stash of liquor hidden somewhere behind a door where one or more people can hide themselves when they need a moment to themselves.

I would never need that around my own family, of course. But I courteously present it as a suggestion to my readers.

Go on to day 8