There's only one catch: sunsets tend to take place right around nightfall, which means you'll also need a place to sleep. The price for that can vary widely over the course of a year in a spot this seasonal. The Greenporter Hotel in cute little Greenport Village, for example, charges $119 plus tax ($133) for its cheapest room on winter weekends; in July 2014, it will be $309 plus tax ($345).
Affordable lodging and a lack of crowds were my primary motivations for heading to the East End on a winter weekend. And something about the Yelp reviews made me suspect I was going to like the Greenporter: "Dumpy motel lying and masquerading as a boutique hotel." "About as much charm as a white padded room." "I mean, come on guys, not for nearly $300 a night."
There, in that last one, did you catch it? Fussy online hotel reviews are easy enough for unfussy travelers like me to ignore; when the reviewers paid more than twice what you plan to, they mean practically nothing at all.
In fact Jeanny, whom I invited as stand-in girlfriend in part because she has far higher standards than I, had no complaints — the overhauled former motel had a decent bed, working Internet and a bathroom with a timed heater (great for winter mornings). Just a clean, private room with hot water is generally enough for me; a flat-screen TV and a front desk that printed out hiking paths (and later, promptly mailed back an item left behind) were bonuses. There's even a smidgen of style — a whitewash treatment alone is enough to transform the vibe from old to retro — and a decent free breakfast. Sure, if I had paid $345, I'd expect a lot more — like to be fired from this column for dereliction of duty.
You also don't need a car to get there — it's a five-minute walk from the Greenport Long Island Rail Road and Hampton Jitney bus stop. Jeanny had driven us out there early Saturday morning, but she left early Sunday; I would stay for the day and take one of the frequent jitneys back, $19 to Manhattan.
Heading to a summer spot in the winter, of course, has its downsides. You can't jump in the water and for after-dark excitement, you'll have to turn to a John Grisham novel. But lines are nonexistent, and service tends to be impeccable, as you've got the full attention of servers and hotel clerks.
Having a car does have its advantages; if we hadn't driven, we wouldn't have stopped for an early lunch at Taqueria Mexico in Riverhead, the last town before Long Island splits. One thing you can count on from wealthy vacation areas is restaurants for immigrant workers somewhere on the periphery. Jeanny began her Frugal Traveler career by absolutely schooling me on ordering: she ordered one chicken tostada ($2) and asked our diminutive Guatemalan server to add beef to a $1.50 meatless tostada, for which we were charged an extra 50 cents. (My $8 order of three pathetic bean and cheese sopes for $8 was half as good for twice the price.)
Once lodging is taken care of, the only danger of blowing the budget in the North Fork is the temptation of the pricey, local-ingredient-obsessed restaurants. Having sensed danger on the drive out when Jeanny had asked, "Where are we having dinner?" I decided to forestall any evening splurges with a snack-as-we-went approach. There were those tostadas, a $4 bag of six still-warm cider doughnuts at Wickham's Fruit Farm (now closed for the season), three homemade pickles for $3 at Goodale Farms and a portion of black bean and grass-fed beef chili with blue corn tortilla chips for $10 from the food truck behind the fancy North Fork Table & Inn.
In between, we fit in a visit to Horton's Point Lighthouse (though you can't enter in the winter), a walk on a nearby beach and a wine tasting at Lenz Winery, which we split for a $10 and which included four wines, including its well-regarded gewürztraminer. Once again beating me at my own game, Jeanny managed to weasel a fifth taste out of our server.
We tried to go see the sunset from Orient Beach State Park, which hangs by a ligament off the tip of the North Fork, but the park closed at 4; a worker there directed us to the causeway, which turned out to be perfect. The evening was young, but night life expectancy is short during North Fork winters, so after dropping off our bags, we hurried over to catch the tail end of the 5 to 7 p.m. weekend happy hour at the Winemaker Studio in Peconic, a combination tasting room, bar and wine shop. Pours were 30 percent off, and we took advantage, ordering normally $7 glasses of a blend of reds from Suhru Wines in Mattituck.
On advice from our server, we decided to end the evening with a drink at the bar at First and South, a fancy-ish restaurant back in Greenport. We found a cozy little small town bar scene there; we chatted up a local English teacher and got filled in on the honors curriculum at Riverhead High School, from Shakespeare to Elie Wiesel. (Jeanny and I first met as teachers in the 1990s, so we were actually quite interested.)
I was a little worried we'd be tempted to eat from the pricey restaurant menu, so, along with a beer, I ordered what turned out to be the best deal on the menu, the $8 chowder loaded with smoked cod and apple wood bacon. Jeanny went rogue and ordered a shockingly insubstantial salad ($9 for "biodynamic" greens) and a bemusingly priced order of fries ($8). She would be paying for those herself.
When Jeanny drove off the next morning, I set out to see just what was within walking distance of Greenport Village. (My plan was aided by some unseasonably balmy December weather.) Quite a bit, it turned out. A list of hiking trails the hotel gave me included paths in Inlet Pond County Park, just off Long Island Sound and about a one and half mile walk north. A Google Maps route sent me over back roads where traffic was limited to flitting robins, black-capped chickadees and the occasional cardinal. Its chosen route into the park, however, led through someone's backyard and into what looked to be thick woods.
After asking for directions, I looped around Sound Drive to just where the park met the water. But a gate and sign — "Private Beach" — stopped me. I was confused: How can a private beach be connected to a public park? But ever since a farmer in Arkansas scolded me for stepping onto his property to take an Instagram photo of some bales of hay, I've been averse to even seemingly harmless property rights violations. So I headed off-road, thrashing into the bramble that lay inside the park, catching my pants on thorns and wishing I had a machete.
Soon, though, I hit a trail, which looped around lovely Inlet Pond and, on several occasions, spurs that led right onto the beach. (So much for private.) Perhaps the walk would have been more traditionally lovely in the spring, but I quite liked the skeletal trees and windblown marsh grasses that gave it barren and blustery look. I came out at the trailhead Google Maps should have led me to in the first place, at a red house on Route 48 used by the North Fork Audubon Society.
From there, it was an easy walk to Kontokosta Winery, just north of downtown Greenport on a bluff over the Sound. The long driveway through the vineyards themselves toward the tasting room — a rather regal-looking barn — makes for a dramatic approach. I'll defer judgment on the wines to a more educated palate, but the servers were quite pleasant and the tasting (along with a walk out to the bluff) was certainly worth $10.
It was not as good a deal, however, as the spot where I ended the trip after wandering through galleries and shops in town. North Fork tastings are not all about wine: at the Greenport Harbor Brewing Company, $8 gets you three ounces of each of seven beers — for a total of more than an English pint. I fell for the hoppy Other Side IPA, as well as for several of the very cute dogs hanging out in what turned out to be a canine-friendly, jam-packed local hangout. What it's like in the summer, when it must fill with city folk, I have no idea — and, come to think of it, not much desire to find out.
For more photos, go to Seth Kugel's public Facebook page or follow him on Instagram, @sethkugel.
This article has been revised to reflect the following correction:
Correction: January 6, 2014
An earlier version of this article misspelled the name of a farm on Long Island's North Fork. It is Latham Farms, not Lathan.
