A Trip to New York: Greenport & NYC

October 3, 2021

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In September we took a family vacation to New York for my cousin’s wedding in Greenport. It turned out to be a phenomenal trip and really blew our expectations out of the water!

Greenport is a small fishing town on the North Fork of Long Island. I was a bit worried about getting all the way out there with a one and half year old, but our travels were amazingly smooth. We took a short flight from Moline to Chicago and then another short flight to LaGuardia. From LaGuardia it was a little over a two hour drive to our condo in Greenport. August was a world class traveler the whole way!

We arrived late and were happy to have a comfortable condo to crash in. We stayed at the Cliffside Resort in Greenport and had a great view of the water from our condo. In the morning we grabbed a coffee at Aldo’s downtown and then enjoyed some delicious pastries from the Blue Duck Bakery. We walked around the quaint downtown of Greenport and let Augie run around at the park and look at the boats in the harbor. There were plenty of cute shops and restaurants and an indoor/outdoor carousel right by the harbor. For lunch the whole family got together and ate outside at Claudio’s overlooking the harbor. We indulged in crab sandwiches, mussels, and lobster rolls. Over Augie’s nap time we decided to drive around to the South Fork of Long Island and see a bit of the Hamptons. The drive was full of quaint farm stands. We drove around the beautiful homes of South Hampton and saw a little bit of Cooper’s Beach. Since Augie was still sleeping we decided to go on and take the ferries back to Greenport. To get from the South Fork to the North Fork via ferry you have to take two, the south ferry will take you from North Haven to Shelter Island and then the north ferry will take you from Shelter Island to Greenport. Both ferries were extremely fast and easy to take. Augie woke up on the first ferry so we decided to stop on Shelter Island and check it out. We stopped briefly at a mini-golf and ice cream place and let Augie play on some of the ride on toys. On Friday evening we went to the rehearsal dinner at Greenport Harbor Brewing Company. They had a fantastic indoor/outdoor area with lots of space for Augie to run around. He went a little crazy, but had the time of his life.

On Saturday morning we went to breakfast at Crazy Beans. The food was great and the atmosphere was a fun, funky throwback. We then went back to the condo and played on the beach. Cliffside Resort has a fantastic private beach. Alex and I took a quick dip in the ocean, which was surprisingly warm. Then my mom and I went to explore of couple of farm stands while Alex stayed back with Augie for his nap. We got some fresh carrots with an incredible ginger dip at the first farm stand. At the next one we sat at a table outside and sipped cider. We got some fresh apples and apple cider donuts to go.

The wedding that evening was absolutely incredible. It took place at Bedell Cellars, which was a beautiful vineyard with amazing gardens. The ceremony was short, but incredibly sweet and was followed by the most amazing cocktail hour I’ve been to. There were tables spread with charcuterie and cheeseboards and tons of fresh farm-to-table faire. There were also fresh shucked oysters and phenomenal hors d’oeuvres. While I had to partake in the mock-tail versions of the cocktails as I was pregnant, they were still delicious. Eventually everyone made their way up to the veranda for dinner and dancing. I’m usually not a fan of taking children to weddings, but as this was a family wedding and our only overnight babysitter (my mom) was also at the wedding with us, we had no choice but to bring Augie (thankfully the bride and groom were wonderfully gracious about this). He did fantastic, although we weren’t able to get him to fall asleep in his stroller like we were hoping. We ending up leaving a bit earlier than we wanted, but all in all it was a wonderful night celebrating two wonderful people.

On Sunday morning we went to a brunch hosted by the father of the bride at the Menhaden. It was nice to be able to say our goodbyes to family and enjoy another awesome spread of breakfast foods and pastries. Afterwards we drove up to Orient Point explored the beach. Over Augie’s nap we drove to the East Hamptons. We got out and walked the beach which looked like a scene straight out of Something’s Gotta Give. The South Fork has beautiful sandy beaches, while the North Fork has stunning pebble beaches. On the way home we stopped at a farm stand that had tons of things for kids to do. Augie had a corndog and enjoyed climbing on all of the tractors. Before bed that evening we enjoyed one last sunset on the beach at our condo.

The next day we packed up our things and headed in to the city for a couple days of exploring. The drive in wasn’t too bad and we arrived at our hotel just as Augie was waking up from his nap. After we got settled in a bit we took a long walk through Central Park. We exited by the Met (which was closed for the Met Ball that evening) and found a little place to have some dinner on the Upper East Side. The people watching was so fun. We loved watching all of the children in school uniforms play at the park while nannies lined the benches.

The next day we explored as much of Manhattan as we could in one day. We walked from Times Square west and then down the length of the High Line down to Greenwich Village. The High Line was a fantastic walk – and one that Augie could get out and explore safely on. We stopped at a park in Greenwich Village to let Augie play for a bit before continuing on to check out the “Friends” apartment building exterior, Washington Square Park, and some of NYU’s campus. We stopped for lunch before walking down to the 911 Memorial. From here we meandered around lower Manhattan and caught a glimpse of the Statue of Liberty from Battery Park. We took in a few of the Wall Street sites for Alex and then headed towards the Brooklyn Bridge. To end our day we decided to take a water ferry from Battery Park back up to Midtown West. It was a long day full of walking, but it was so much fun to be in a city again after almost two years of a pandemic.

The next morning we left to catch our plane in LaGuardia (which by the way took us an all of 38 minutes to get from our hotel in Times Square, drop off our rental car, get through security – with a checked bag and baby – and find our gate!). All in all it was a wonderful trip to New York, full of lots of new experiences and sites for the whole family.

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