Where to Eat, Drink, Stay, and Play in Greenport, NY
It's all wine, farm stands, and fun.
A few months ago, I spent the most lovely four days in the North Fork (sandwiched between a couple nights in Brooklyn) and let me tell you, it’s easy to get there from the city. If you have a car, that’s the best way, of course. But the train was just as easy and dare I say even more stress free? Talked about the trip briefly here:
August Updates from the Road
Since the month is almost over (and I spent the majority of it traveling domestically), here are a few quick and fun updates!
But then, I wrote a really fun renovated motels story for Thrillist that included Silver Sands, an absolute dream of a hotel in Greenport, along with 10 other hotels from Ojai and Nashville to Miami and Santa Fe. Though the North Fork tends to be seasonal in terms of hiring (lots of college kids work at the bars and restaurants in the summer), I can imagine it being just as wonderful —likely quieter, which I don’t mind —all year long.
Traveling to Long Island in the near future? Here’s some insight on hotels, wineries, distilleries, and other things to do. You won’t want to leave.
Eat & Drink
Restaurants: Encanto Crepes & Cafe was perfect for a Colombian breakfast or midday pick-me-up. And Alpina, a cozy Alpine restaurant with a bar that extends along the wall, is a must. Expect menu items like Weiner schnitzel, foraged mushrooms, duck, and lots of cheese and charcuterie. I’m still sad I was too full to try the chartreuse souffle with Alpine chocolate sauce. Snag a bar spot at Little Creek Oysters for oysters, of course, but also smoked fish dips, crab rolls, and tostadas. Eddie’s at Silver Sands is seasonal, but Nookies is open year-round and the Halyard at Soundview Greenport feels like somehow you teleported to Malibu (sit outside and watch the sun fall into the ocean). I did hear good things about North Fork Table & Inn, but didn’t make it there this time.
Wineries and distilleries: there are over 50 wineries in the North Fork of Long Island (thanks to its Bordeaux-like climate). These were a few I went to and liked in no particular order: Kontokosta, Rose Hill, Sparkling Pointe, and Croteaux. In Greenport’s Main Street area, you’ll also find Matchbook Distilling, a woman-led spirits brand and tasting room open every Saturday. Try the amaro, gin, whiskey, and more here.
Stay
You already know how I feel about Silver Sands and if you can’t remember, refer to the Thrillist link above. Hoping to visit again and again.
Lin Beach House definitely had its charm, too. It’s a six-room property just a five-minute walk from Kontokosta, which is a huge plus. They have a daily make-your-own-cocktails style happy hour for guests at the bar, which is very cute. And there’s plenty of space on the property to read, hang out, and have a drink. The shower in my room was wild (it had like 5+ shower heads and nozzles, I kid you not), but otherwise my night here was very enjoyable. I like that the inn provides little guides of things to do in the area and that my suite had a balcony (I stayed in the Bianca). The folks who own Lin also own Matchbook Distilling so you will find their products for sale at the inn’s gift shop, a nice touch. Can’t forget to mention that if you stay here you are also a quick walk to 67 Steps Beach, which wasn’t swimmable the day I was there, but it is quite beautiful and a great place to meditate if you find a big, smooth rock to sit on.
I also stayed at the Harbor Front Inn right in town. It is an older hotel, but nice and clean with friendly staff, free breakfast, and it’s in a walkable area, has a pool, and balcony rooms overlook the marina (charming). Its sister property Sound View looks like a wonderful place to stay, as well, but I only went over there for drinks and a bite. As mentioned above, snag an outdoor table at the Halyard, but honestly the dark interior piano bar was pretty fun, too.
Hotel Moraine is probably the priciest hotel in the area, but the most luxe. It’s billed as a family resort and I did see a couple babies around, but there weren’t kids running rampant or anything. I think it’s worth a stay if it doesn’t break the bank for you. I walked over there from Lin Beach House (wouldn’t recommend because there really aren’t any sidewalks) and caught the sunset by the pool with a glass of local rose. Absolutely stunning. They had heaters on and a mix of hotel guests and (seasonal) locals sat around chatting in sweaters and blankets.
Play
Not going to lie. I got a little lazy here and employed AI to help me with this last section. I don’t have to tell you why things have felt extra heavy this week, but you know. The point is, if I didn’t do every single one of these things, they are on my list for next time.
Stroll the Historic Downtown: Greenport’s charming downtown is filled with quaint shops, art galleries, and great restaurants.
Shop at White Flower Farmhouse: For those who love farmhouse decor and coastal-inspired homeware, this boutique is a must. The shop features rustic, vintage-style decor, including hand-poured candles, coastal art, and other chic home accessories.
Explore Mitchell Park and ride the carousel: This beautiful park is right on the waterfront and features an antique carousel—great fun for families or anyone looking to relax. You can grab a coffee at the adjacent shop, but it wasn’t very good. Park yourself on a bench, watch the birds, and contemplate life. Catch sunset views and enjoy live music during summer evenings.
Maritime Heritage & the East End Seaport Museum: Learn about Greenport’s rich maritime history at the East End Seaport Museum. You can also see the Bug Lighthouse on a boat tour, a beloved local landmark.
Sail or kayak on the Peconic Bay: Rent a kayak, paddleboard, or sailboat to explore Peconic Bay. Local companies like Peconic Water Sports offer rentals and guided tours, or book a sunset sailing tour for a relaxing experience. Reminder: if you stay at Silver Sands, they have kayaks available for guests to rent.
Lavender By the Bay: Just a short drive away, Lavender By the Bay is said to be one of the most beautiful spots on the North Fork during bloom season. Wander through fragrant lavender fields and pick up some lavender products to bring home.
Stop at the local farm stands and markets: The North Fork is filled with fresh farm stands and markets, where you can find local produce, pies, and artisanal products. Harbes Family Farm in Mattituck offers a little bit of everything, including a corn maze and pumpkin picking in the fall, cider donuts, and even wine tasting.
Ride the Shelter Island Ferry: Take a quick ferry from Greenport to Shelter Island for a fun day trip. It’s a great place to bike around or visit nature preserves, such as Mashomack Preserve.
Last, but not least…
How to get around:
Walking is not recommended unless you are in one of the downtown areas with sidewalks. Having a car is preferable. If you don’t, seek out a local taxi and make sure to have them on speed dial. It wasn’t too hard getting an Uber during the day, but at night it was actually impossible.
To reach Greenport from New York City, you have a few easy options. One popular choice is the Long Island Rail Road (LIRR), which you can catch from Penn Station or Jamaica Station. Take the Ronkonkoma line, transfer at Ronkonkoma to the Greenport branch, and expect a journey of about three hours costing $20–$30 one way, depending on peak times. Since direct service to Greenport is limited, especially on weekends, check the schedule ahead. Alternatively, the Hampton Jitney’s North Fork Line departs from various points in Manhattan and reaches Greenport in 2.5 to 3 hours, with one-way fares between $30–$40. Reservations are recommended, particularly during peak travel times.
For those who prefer driving, you can take I-495 (the Long Island Expressway) eastbound, connecting to Route 25. This route leads you through the North Fork’s scenic wine country and directly to Greenport in about 2.5 hours, though travel time may increase during peak travel hours. Keep in mind that certain highways and bridges along the way may have tolls.
If you’re coming from Connecticut or the northern suburbs of NYC, taking the Cross Sound Ferry from New London, CT, to Orient Point, NY, might be the most convenient option. The ferry crossing takes about an hour and 20 minutes, followed by a short 15-minute drive to Greenport. Each option offers its own scenic journey, so choose what best fits your schedule and travel preference.