Thanksgiving Weekend in New York City


For the second year in a row, I was lucky enough to spend Thanksgiving in New York City with my younger sister, Angie. Last year, while I was interning in the city, she came and stayed with me in Manhattan. This year she got to see the best of both worlds – the city and Hoboken (aka the better part of the world). From finding a place to eat Thanksgiving dinner to Black Friday shopping and sight seeing, there were so many adventures that quickly filled up our schedule. And after two years of spending the holiday weekend here, I’ve definitely learned a thing or two. So if you’re considering a city getaway for next year’s holiday, check out all the activities we did each day for the best Thanksgiving weekend in NYC.


It’s almost always cheaper to fly the morning of Thanksgiving rather than the day before. Last year Angie flew in super early so we could go to the Macy’s Day Parade, which we decided to pass on this year (standing outside for hours and hours in the cold? No, thanks). This year she arrived at my apartment around one. After we fueled up on homemade chili (you’re welcome, Angie) we went to the city right away. We spent our day sipping coffee and strolling around the upper east side. We, of course, stopped by The Met to take pictures on the steps (cue the Gossip Girl opening music).

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After walking around for a few hours, stopping to snap pictures of Central Park’s colorful trees, Macy’s holiday windows and other decorated store fronts, we eventually made our way back to New Jersey – mainly because almost everything was starting to close, if not closed already, for the holiday. We had an hour before our dinner reservation so we decided to stop at a bar right near the Hoboken PATH (it was actually the only open bar around). Lucky for us, Hotel Victor Bar & Grill has happy hour every night of the week until 8 p.m. Thanks for the pre-dinner buzz, Hotel Victor!

Before I get into our dinner details, I should start by saying I’m not a huge Thanksgiving-food fan. My sister on the other hand, could probably eat turkey and mashed potatoes every night. Since there was only two of us, we went out to eat both years. Last year we ate at Pera Soho, an elegant Mediterranean restaurant in the heart of Soho. For $49 per person, we each got a three-course meal. We both went with the Roasted Pumpkin Soup as an appetizer (delicious!) and the Traditional Whole Roasted Turkey as an entree (eh). The sweet potatoes that the entree came with were delightfully sweet, but I definitely could have gone without the turkey. It was a bit dry, and even my Thanksgiving-loving sister agreed. For dessert Angie got Pumpkin Pie, and I got something chocolate (obviously).

This year I made reservations at The Brass Rail, a modern American restaurant with an old-school charm in Hoboken. For a prix fixe of $45 a person, we would each get three courses. What first attracted me to this Thanksgiving menu was the amount of different options they had for each course, and when I saw they had steak as an entree.. game over. For an appetizer I ordered the Roasted Chestnut Soup, which was scrumptious in all its creamy goodness.

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Angie ordered the Lolla Rosa Salad, which had candied pecans, raisins, goat cheese and a tangerine-honey vinaigrette. It was so good she ended up eating almost all of it instead splitting both of the appetizers like we had agreed on (rude). She ordered the Roasted Turkey Dinner, and I got the Grilled Filet Mignon.

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Being in NYC for Black Friday can be magical or horrible, depending what type of person you are. If you’re a big shopper, like both my sister and I, and don’t mind crowds (and I mean really big crowds) then it’s definitely the place to go. And if you’re an avid Black Friday shopper then you know in order to take advantage of big department store sales, like Macy’s, you definitely need to go early!

We took the PATH to 33rd street and walked over to 5th avenue, where we started our fashion-focused journey. We stopped in many, many stores – like H&M, Zara and Top Shop, just to name a few. My favorite stop of the day (on the corner of 38th and 5th) was Lord & Taylor, which is actually the oldest luxury department store in North America. They had clothing up to 50% off (on top of their already pretty amazing sales) and tons of shoes up to 20% off – aka heaven.

When we got to E 40th street, we decided to take a break and headed to Bryant Park for their yearly Winter Village.

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If you’ve never been before, this is a MUST. More than 120 merchants – selling art and crafts, jewelry, clothes, house hold items and more – fill the park through early January. There’s also a ton of vendors with comfort foods (like Super Mac + Cheez at kiosk L4) and delicious treats (like Woops! Macarons & Cookies at kiosk 9).


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Southwest Porch (located near the southern end of the Fountain Terrace) is the perfect place to grab a cup of hot chocolate, kick back and relax around a fire pit. Seats around the pit are a hot commodity, but the surrounding tables have near-by heat lamps so you’ll be toasty no matter what. It was oddly warm this Thanksgiving week so we opted for iced lattes from a cute bakery and cafe called Le Pain Quotidien (located just north of the Fountain Terrace on the 6th Avenue side of the park).


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After Bryant Park, we continued up 5th Avenue until we got to 59th street. We headed west, walking through Central Park to get to our next destination: The Time Warner Center at Columbus Circle.


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Saturday was actually Angie’s birthday (woo!), and the one place she wanted to go celebrate at was The Sugar Factory. The Sugar Factory is known for their 60 oz. goblet “candy” drinks. It’s $36 for one drink, which is pricey but definitely in line with typical meatpacking district prices. Plus, the drink is big enough to split between two people! We chose the Passion Punch drink, which was poured over a goblet glass of dried ice, creating a smokey effect. The drink itself was super sweet, but we were expecting that being in a “candy” restaurant and all. Since we weren’t super hungry but knew we needed to eat something, we ordered a side of fries to split. The manager was kind enough to offer us a free dessert (to which we gladly accepted and dipped our fries in shamelessly). The dessert was a platter (literally) of ice cream and delicious toppings. They even put a sparkler in it and sang to Angie for her birthday!

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From there we walked a few short blocks to the Chelsea Market, one of my favorite places in that area. It’s a block-long indoor marketplace with SO MUCH inside – retail stores, knick-knack shops, flower stands, bakeries, urban eateries, grocers and even a wine vault!



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A few of the places I’ve really enjoyed eating at in the market are: Farm to Table, Chelsea Thai and Doughnuttery. If you need something to quench your thirst, stop by The Filling Station for a craft beer in a cute mason jar, which you get to keep for an extra $2. Later that night after grabbing a slice (OK.. a couple slices) of pizza from Basile’s Pizza in Hoboken, Angie and I walked along Washington Street popping in different local bars here and there.


Come Sunday, we were exhausted. After catching up on some much needed sleep, we snacked on goodies and coffee at Choc O Pain, a French bakery and cafe in Hoboken. We got a chocolate croissant and a ham and cheese quiche to split (which were both phenomenal), along with two milky lattes. We stayed there for quite some time before hitting the local boutiques. Although there’s a ton of different shops in the area, my top three favorite are: Dor L’ DorDear Hannah, and Ruby and Jenna. If you walk along Washington Street, you can’t miss them! We also walked along the river to get some city skyline views. If you’re looking for the BEST skyline view and some pretty good food to go along with it, make a reservation for a patio table at The Liberty House Restaurant in Jersey City – I promise you won’t regret it. Angie and I both really wanted to go, but we were honestly still so tired and still pretty full from our bakery treats earlier that day.


So instead, we picked up some cheese (gouda and brie), olives and a bottle of Pinot Grigio for two. If you’re as obsessed with cheese and wine as we are then you absolutely need to check out Cheese + Wine. It’s a little bit of a hike from Washington street but definitely worth it, and the customer service is fantastic. We ended our perfect holiday weekend together with a glass in hand, relaxing on the couch watching Netflix (so basic, I know); and I wouldn’t have wanted to spend it any other way or with anyone else (awwww).


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