How to Spend a Perfect Fall Weekend on Long Island’s Relaxed North Fork

While the Hamptons offer summer fun, Greenport was made for autumn

October 31, 2023 7:35 am
Sound View in Greenport on Long Island's North Fork
North Fork, Long Island
Read McKendree

New Yorkers looking for a fall weekend away typically turn north, towards the Hudson Valley. This is of course justified as the region is unquestionably an autumnal wonderland. But if you’re tired of following the crowds and willing to swap rocky hills and trees for rocky shorelines and vineyards, allow us to suggest looking east for your next fall getaway, to the North Fork of Long Island. 

If it’s been a while since you’ve seen a map of Long Island, here’s a brief geography lesson: At its eastern tip, Long Island splits into two peninsulas, known as the South Fork and the North Fork. While the South Fork is famously home to the Hamptons, Montauk and the hullabaloo that comes with them, the North Fork is home to bucolic farms, wineries, oysters galore and marinas more populated with humble sailboats than flashy yachts. Overall, the North Fork is relaxed and down to earth, not a place to see and be seen. Instead, it’s a place to slow down and reconnect with yourself, those traveling with you and the land. And all this, by the way, is under 100 miles from NYC.

To explore everything the North Fork has to offer, base yourself in Greenport, a whaling and ship-building village settled in the late 1600s that maintains its historic charm and a thriving little downtown. I’ve personally been visiting the town for over 15 years, mostly in fall, and am sharing with you here my go-to spots and insights. Allow this to point you in the right direction, but don’t be afraid follow your senses, explore and forge your own path too, as making your own discoveries among the area’s embarrassment of riches is often the best part of any trip to the North Fork.

How to Get There

If you’re coming from the west (New York City and beyond), there are several ways to get to Greenport. Arriving by car is the most straightforward and can take under two hours from midtown Manhattan if you time your departure right. Having your own vehicle will also give you the most freedom to explore the North Fork with ease. If you’re a city dweller without a ride though, not to worry. Greenport is the last stop on the Main Line of the Long Island Railroad (you’ll get dropped off directly in town) and the Hampton Jitney runs bus service from NYC too. Once you’ve arrived, you won’t need a car to explore Greenport itself, but you will need to pull up your ride-hailing app of choice to visit nearby farms and wineries. 

If you’re coming from the north (Connecticut and New England), drive your car onto the Cross Sound Ferry from New London, Connecticut to Long Island’s Orient Point. From there it’s just a 15-minute drive into Greenport.

The Halyard restaurant at Sound View hotel in Greenport
The Halyard, a restaurant at Sound View.
Doug Young

Where to Stay in Greenport

Greenport is home to a small handful of boutique hotels, the most design-forward and centrally located of which is American Beech. While it’s positioned in the middle of the action and is a summertime hotspot, it offers a more mellow vibe come fall. Their thirteen rooms (which includes two two-bedroom apartments) are spread throughout a grouping of historic buildings collectively known as Stirling Square, which also houses American Beech’s restaurant and their three unique bars. Of note: Your stay comes complete with a bike rental, which facilitates an easy, 10-minute ride to the nearest beach. 

If you’ll have a car, consider a stay just outside of town at Sound View, an old motel that’s been reimagined from top to bottom. The property is perched partially on pilings above a rocky private beach, directly on the Long Island Sound, so you’ll get your fill of water views and lapping waves. Mid- and upper-tier rooms come with private decks and kitchens, while their hot tub suites come with wood-fired, cedar hot tubs — ideal if your trip to Greenport is of the romantic variety. There are also two places to eat and drink onsite, both of which are worth a visit whether you’re spending the night or not (more on those below). 

If you’re into Airbnbs and looking for space to spread out with family or friends, Greenport has a top-notch collection of homes to pick from. Many, like these, are full of character and history, and will put you within walking distance to the center of town.

The Piano Bar at Sound View hotel in Greenport on Long Island
Among Sound View’s dining and drinking options is an intimate piano bar.
Emily Nathan

Where to Eat and Drink in Greenport

Start your day at Aldo’s Coffee. The smell here alone is worth the visit as they’re often freshly roasting coffee beans in their big vintage roaster. Get a cappuccino with freshly shaved chocolate on top and don’t leave without one of their homemade scones. For a heartier, casual breakfast, check out Crazy Beans, which channels a 1950s diner with its checkerboard floors and red leather seats. If a grab-and-go option best suits your morning schedule, you can’t go wrong with a classic breakfast sandwich from Sterlington Deli

Come lunch, if you’re in Greenport and not already out exploring, few places are more picture perfect than Little Creek Oyster Farm & Market, a tiny shack shucking fresh oysters at the water’s edge. A couple blocks away in Stirling Square, the brick oven pizzas from 1943 Pizza shouldn’t be missed. Then, take the one-minute stroll to Greenport Harbor Brewing Company, the beer maker’s original brewery and tasting room housed in the town’s old firehouse.

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For dinner, Greenport and the North Fork offer plenty of worthy options. For a white tablecloth experience, North Fork Table & Inn offers three- and four-course prix fixe menus. Over at Sound View, their restaurant, The Halyard, supplies both indoor and outdoor seating with Sound views and a menu utilizing the bounty from local farms. In Greenport proper, Noah’s is a local-approved spot that’s been serving farm-to-table cuisine for over a decade. Claudio’s Tavern & Grill is another institution with can’t-go-wrong menu items like steak frites and fish and chips.

To round out your night, check out American Beech’s playful Black Llama Bar for an exquisite after-dinner cocktail. And back at Sound View, visit the Piano Bar, which was left perfectly and purposely untouched during their renovation and features live music every Tuesday and Thursday, plus piano karaoke on Wednesdays.

Croteaux Vineyards
Croteaux Vineyards
Croteaux Vineyards

What to Do in Greenport and the Greater North Fork

The main draws of the North Fork are the wineries. There are far too many to visit in a single trip (which means you’ll have reasons to come back), so here are a few sure bets to get you started.

First and foremost, you’ll want to visit The Old Field, which flies under the radar but is a true hidden gem. This entirely unpretentious winery oozes pastoral, Americana charm with its old red barns, duck pond complete with weeping willow and freely roaming chickens. Plus, during cooler weather, a wood-fired stove keeps the homey interior spaces feeling cozy. More solid choices which couple good wine with beautiful settings include Lenz, McCall and Croteaux Vineyards (which, heads up, only produces and serves rosé). Lastly, Kontokosta is also appealing for being the closest winery to downtown Greenport (five minutes by car, 10 by bike), making it a great choice if you’re strapped for time or transportation.

Fall is also the best time of year to visit the North Fork’s farms and farm stands. Stop by the tiny shop at Catapano Dairy Farm to pick up fresh goat cheese to snack on while wine tasting. (Note: some wineries allow outside food and some don’t.) For the carnivores, the butcher shop at 8 Hands Farm offers grass-fed and organic meat, including bacon sliced to order (get this along with their fresh eggs if you’re staying in an Airbnb and cooking your own breakfast). Grabbing a homemade pie from Country View Farm Stand should also be seriously considered. Finally, Harbes Family Farm offers a one-stop-shop of all things fall with a pumpkin patch, corn maze, farm stand selling apple cider donuts and an eight-acre Barnyard Adventure park. If you’re traveling with young kids, expect to spend a few hours here. 

Back in Greenport, tame yet scenic pursuits include walking along 67 Steps Beach, a unique, entirely stone-covered stretch along the Long Island Sound, and taking a 45-minute harbor tour on the all-electric Glory


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