Greenport, NY Travel Guide

Somehow through Instragramming, I came across this adorable town in NY and it just seemed like the perfect Fall Getaway that was relatively local. We were supposed to go to Florida, but had to cancel the trip because of the “red tide,” so I needed to come up with something fast to replace it.

We were excited to travel with Jack, but were nervous flying, as I’m sure most new parents are. This really ended up being a great little getaway and I plan on doing a whole post on traveling with an infant soon to help any of you new Moms be prepared.


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We found this quaint, but modern hotel right on the Long Island Sound, at the Soundview Inn. I loved that all the rooms were waterfront and it seemed like it was a super short distance from everything that we were looking to do. IMG_2690.JPGIMG_2692 2

IMG_6772 2IMG_2698The lobby area was beautiful and they had a great continental breakfast every morning. The views here were remarkable regardless of where you were on property. This was our first time traveling with Jack (now 5 Months old), so having a quick/easy bite before we headed out was exactly what we needed.

They also had a fitness center, bike rentals, a pool and restaurant on property, The Halyard. The certainly had other amenities and activities, but we weren’t there long enough to take advantage of them. The last night we were there they actually did Marshmallows fireside for guests!


We didn’t really have much planned for our 3 day road trip, but by the time we got to the North Fork, my husband and I were starving and needed to get out of the car. What should have been a 3.5 hour drive, took 5 hours (thanks Jack lol). We randomly picked Clovis Winery to stop at to grab a much needed glass of wine and snack.

If you’ve never been to the North Fork, there are wineries everywhere. I mean everywhere!

It’s so hard to pick which ones to stop at, especially if you don’t have recommendations or suggestions from friends.

For whatever reason, this was our random selection and the wine was great as well as the view of the vineyard!


We picked up a bottle of Rosé, and headed back to the Soundview to get changed, had a glass and headed out for dinner!

IMG_6381 2IMG_2352.JPGOne thing we did notice when we were looking for a place to eat, was that most things IMG_6308tend to be closed on Wednesdays which was a little odd. It also seemed like a lot of businesses were getting ready to have off-season hours or close up for the Fall/Winter, so ideally, I would like to make this a 1st-2nd week of September trip for that reason alone.

The Mexican place had great reviews on Trip Advisor, and it was recommended by the hotel, so we went to Lucharito’s for dinner. It was kid friendly with great quality selections and food.


Before we headed in to eat, we did a quick walk around town hoping that Jack would fall asleep. Everything is so centralized on the water. It’s such a beautiful little town with really cute shops and restaurants.


The following day, we headed to Bruce & Son for brunch. This place was incredible and can’t rave about enough. I’ve been Dairy Free since I’m still Breastfeeding and this place had the most allergy conscious and accommodating menu. Everything was absolutely delicious as well!


I had the Matcha Pancakes with Brown Sugar Bacon. My mouth waters thinking about that bacon!


Next we took a drive out to the end of of Orient to check out the park and lighthouse. This was us trying to get Jack to nap again… and we were quite unsuccessful haha – it was a nice drive though. They had a really cute park on the beach for kids with a lot of swings in the sand. IMG_2413


Next on our list was Lavender By The Bay. Even though the lavender wasn’t in bloom, it was still stunning and smelled amazing! We didn’t get to go in the gift shop because Jack decided it was time to leave. IMG_2497IMG_2492

Our nextIMG_6569.JPG stop that day was the Kontokosta Winery.

I admit to scoping this place out before hand, and I think it’s property is what drew me to it.

I’ve never been to a winery on the water like this before and it just seemed unique. It was beyond stunning and the wines were incredible.

You can only purchase wines by the taste or glass, but you can take your wine out towards the cliff and hang out with this view.


The one place I had wanted to go to for lunch, Little Creek Oysters, didn’t open until 5pm, so we headed there before going back to the hotel. I could have spent the day here guys. This was such a cute little nook that had shuck your own oysters, although I opted to have someone do the work for me.




Okay… last thing, I swear!

We headed back to the room, and got ready for dinner… not before getting some adorable pictures with Jack in front of this Instagram perfect shack! I could only imagine how awesome this is during the summer!

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We had an early dinner during sunset at the Halyard, and I think that’s what made it so special. You can literally watch the sunset from anywhere on the hotel property, but this dinner view was stunning and our meals were great too.


All and all it was a great road trip and we actually want to book another trip here next September! I think it’s a great family destination that is relatively local for anyone in the tristate area.


If you’ve stayed on the North Fork or anywhere in eastern Long Island, I’d love to hear from you! We’ve never been to the Hamptons or Montauk and would definitely want to make a longer trip out it next time and visit there as well!

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Meghan Mosakowski

lifestyle + wellness coach