Greenport, N.Y., is best known for its maritime history and colonial charm. While this harborfront village is a popular summer destination, I prefer to avoid the crowds and higher prices that come with traveling during peak season. As it turns out, Greenport has a lot to offer in winter. You just have to do a little research because some places are seasonal, or the hours are in flux.
Where to stay
Staying in Greenport understandably comes with a hefty price tag in the summer. So the winter is where you’re going to score the best deals. There are no large chain hotels, so the choices of lodging are all incredibly unique to the area.
This 55-room property has easily the best views of the Long Island Sound. My favorite detail is the cedar lined walls, giving the rooms a cozy touch in the winter. I don’t mind the water being too freezing cold for a dip; just listening to the waves crash outside the balcony is enough for me.
One huge bonus: All the rooms have waterfront views. I recently stayed in the Deluxe King for only $156.00++ per night. This same room in the peak season goes for $726.00++.
Right in the heart of downtown, this boutique hotel is just steps away from the shops and restaurants. The owners of this 16-room property boast about its luxury and attention to detail. If you love Restoration Hardware, this is the place you’ve been dreaming of.
I fell in love with the clean, white minimalist style. The Menhaden also makes sure its winter guests have an enjoyable stay. I think what I loved even more was the Galley, a shared kitchenette space stocked with coffee, chips, cookies, sparkling water and more. Check out the Winter Bespoke Experiences, which include off-site excursions starting at $75 per person.
This spot is perfect for a younger, livelier crowd, with sleek and mod accommodations. This is my pick for a friends’ getaway.
This stunningly renovated 1800’s salt box-style VRBO is a short drive from downtown. I appreciate when someone has respect for the history of a home and its area. From the kitchen fireplace to the gas lamps in front, this 2 bedroom, 2 bath home-away-from-home feels like a trip back in time.
Where to eat
There’s one important rule about visiting Greenport in the offseason: You must call and make sure the restaurants are open — even if Google says they are — as some operate with limited hours. I definitely showed up to a few places to find them closed, so here’s hoping you don’t make my mistake.
Attached to the Sound View, this restaurant also has stunning water views. You can taste their commitment to locally sourced food and ingredients while watching the Sound lap on the beach outside.
Simply delightful, this is by far my favorite menu because it’s so versatile. Plus, I’m on a Cacio e Pepe kick lately and I love their version with Pastina.
Since I have such a hard time finding good barbecue on Long Island, this gem was somewhat unexpected. The 16-hour smoked Texas-style brisket, ribs, and smash burger were my personal favorites, but the menu is huge and makes you want to try it all.
This is a small plate, farm-to-table restaurant that prides itself on its relationship with North Fork farmers and fishermen. It’s got great views of the harbor with plenty of natural light. According to the website, Noah’s takes a short winter break and reopens each year in February.
Now, I don’t eat duck, because I find them too adorable, but I’m told the duck barbecue is the tops.
A kick-back Taqueria and Tequila Bar best enjoyed with buddies. The Lucha Libre theme makes for a really fun time. Can’t go wrong with the Carne Asada Taco with some tequila shots.
More travel: How to spend a magical 48 hours in Beacon, N.Y.
Where to drink
This Swiss-Italian-inspired restaurant and wine bar makes for a quintessential cozy winter evening. The attention to detail did not go unnoticed, as they tout a beautifully curated menu for both food and drinks. And that decor! I would never expect to find anything like this on Long Island.
After I finished my charcuterie, I went to try another bar, then came right back to Alpina. Probably the only time I have been to a bar twice in one night. Absolutely love this place.
Head downstairs to the Sunset Room for all the speakeasy vibes. A fun spot to grab a drink and pizza. Evan, one of the bartenders is quite known in the area for his infectious personality and excellent cocktails. He recommends the daiquiri. I do too!
This place feels like a spot Andy Warhol would party in. Located at American Beech, the cocktails are as creative as the exotic decor. You will have a lot of fun at this bar, and probably take lots of photos.
What to do
Check out the 100-year old Antique Carousel (operating weekends only during off-peak season) and the ice skating rink.
If you’re going to be in Long Island’s oldest town, you should really check this out. Located in the East End Seaport Museum, watch and learn as the blacksmith showcases an old-world tradition of forging iron. Certainly one of the most memorable parts of this trip. Winter hours are by appointment.
Grab a pint and hang out in the brewery’s original 1860’s firehouse location. Tours available Sundays by reservation.
In neighboring Southhold, less than five minutes from Greenport. Their petite-sized tasting room holds up to six guests. I personally loved hanging out and doing a tasting in their homey Yurt.
Picture a winter glamping experience, but for daytime wine tasting. Located 20 minutes away in Mattituck, this is a worthwhile excursion where you’ll reserve a wine and meze pairing in their heated Bergen Road Bungalows.