Fall Weekend Guide to New York City

Updated: Dec 16, 2020

Will K's heart ever be in love with another city more? Will K & K reunite for another weekend in NYC? xoxo, gossip girl.


New York City and I have a long, beautiful relationship that has stemmed my entire life. I first visited NYC when I was 10 years old and I told my mom that this was the place I wanted to live someday. That dream never really went away, and I was offered a position to work in a bridal shop in the garment district in 2014 (fun fact). However, after spending less than a year in San Francisco, I soon realized city life was simply not made for me.

Visiting New York City is an incredibly special experience and I could not think of a better time than September to fly to the Big Apple.

One of my best friends, Kelsey, lives in the nearby town of Orangeburg and last fall we spent a weekend exploring this incredible city and I plan to do so again this fall. My biggest issue with NYC? There is never enough time to do everything.

Honestly, if I had 6 months in this city I probably still would not have time to do all the things I wanted to do. New York City will continue to be a growing list of do's, but I am condensing down this post into the specific places I was able to visit. TRUST ME, another NYC post is in the works literally as I write this one.

Where Do I Stay

NYC is a huge city, and it is truly hard to narrow down where exactly to stay. Everyone has their own way of determining what place is best for them, however, I like to go off what is most centrally located to most major attractions on my bucket list.

Keep in mind, everyone is different with this! For me, I wanted to be walkable to central park, but also close to other major parts of the city like the flatiron district. The Upper East Side fit my needs perfectly as it was a short walk to central park, the met, & other delicious restaurants. The great part about the upper east side is there are many subway stations close as well if you are looking to utilize public transportation during your stay.

I snagged this airbnb which was only a 10 minute walk from the subway station and perfect for 1-2 people. One thing I will note, prep yourself if you have a lot of luggage as most air bnbs are walkups with elevators that take ions of time.

More money to burn? The Courtyard Marriot Manhattan, the Bentley Hotel or the Franklin Hotel all are good options in the same geographical area.

Where Do I Eat

I'm laughing so hard at the photos above because these are probably the least ascetically pleasing photos anyone has ever posted on a blog. But come on! This blog is real, and sometimes we inhale food quickly enough that there is simply no time to get out a real camera and take a photo.

This is a loaded topic as there are honestly way too many places to fathom going to when visiting New York City. As a huge foodie, I sometimes spend hours deciding on the perfect restaurant on Yelp or get too overwhelmed and end up somewhere dismal. Needless to say, my anxiety pivots as hard as Ross in the stairwell on Friends.

Sure, there are bad food spots no matter where you go, but around every corner in NYC there are some pretty ones. No matter the food situation however, please do yourself a favor and grab a bagel at least somewhere in the city. Before visiting, I was told by every person I knew "the best" bagel spot to try and honestly I was pretty overwhelmed as a carb lover. Here are a few that have stood out to me:

H&H Bagels: I went here during my last visit. So delicious, accommodating to my cheese-less life (but looked at me like I was nuts). Visited the Upper East Side location, but you can find another location on the Upper West Side as well.

Black Seed Bagel: This spot was recommended by a previous NYC local friend of mine. Another proclaimed best bagel spot, this spot is actually a little more "hipster friendly", meaning there are more places to sit and talk about Nietzsche. There are several different areas of NYC these guys can be found, but the East Village locale stands out as a fan favorite.

Tompkins Square Bagel: Another local recommendation, this is the place to go if you have a friend that is just "not that into bagels" but it's your moral imperative to prove her wrong. Tompkins square serves up not just bagels, but rainbow colored pancakes. A true basic betch paradise. Located in NOHO & just outside East Village.

After you eat that, get ready to get precisely 1 hour later because you will eat every hour you are in New York, it is amazing. Here are some restaurant tips broken down by district:


Joes's Pizza: You have probably at least heard 1 or 2 bloggers or former bachelor contestants talk about this spot. Known for it's classic New York style pizza, this is a great spot to grab a local slice. They also have multiple locations around the city.

Le Bernardin: A true "special occasion" french restaurant, this is a great spot to get a really nice dinner while visiting New York. Splurge on at least one meal while you are there as this city serves up some of the best food housing the most renowned chefs from across the world.

Upper West Side

Playa Betty's: Now, I'm a little skeptical of Mexican food anywhere but my home state of California, but this comes highly praised by my best friend who resides in Southern California part of her life. This is a big deal ya'll. Check out their eclectic brunch menu.

Upper East Side

Shake Shack: Don't worry guys, see below for an actual NYC rec. I put this on here as most California people do not have a Shake Shack near them and it is always fun to try. Growing up an In n Out child, it is hard to compare the two as well...In N Out is better. However, I can see the appeal and the criss cut fries are bomb.

Alice's Tea Cup: One of the places I was able to visit during my time in New York, this was such a fun spot to try. After my trip to London, I kind of fell in love with the idea of afternoon tea. Why is this not more of a thing? Should I open my own tea shop in Austin? Burning questions. Enjoy the jasmine tea and in house made scones.

Hell's Kitchen

Magnolia Bakery: Between the daily cupcake menu, & selection of mini pies and cheesecakes, this is a non basic place to get an unreal dessert.

Lower Manhattan (Little Italy)

The Original Benito One: If you know me at all, one thing I am incredibly passionate about is Italian food. I grew up in a primarily italian household with pasta being a daily staple in my diet. I know a good bowl of pasta and I know a shitty one. This was one of the best Italian restaurants I have ever been to. Remember when I was discussing my anxiety with picking restaurants? Poor Kelsey watched me frantic on Yelp trying to pick the perfect place. and I must say, we sat down and the people next to us were FROM Italy and spoke zero English. Sometimes, I know what I'm talking about.


The Meatball Shop: I could kick myself that I did not get to go here for my last weekend in NYC and you best believe I am making whoever I'm with go with me the second my plane touches down. Meatball sandwiches..I really do not know what else to say.

Where Do I Drink


Well...I do, but let's talk about nonalcoholic things first so I do not seem like a total degenerate.

With the weather in fall cooling down the normally humid summer city, it is fun to get a hot drink fix. Cha Cha Matcha (around the corner from Little Italy) is a fun spot to visit to snag a hot matcha drink. For those of you unfamiliar, matcha is a green tea latte type drink that actually has a lot of healthy properties to it as well as a less intense version of caffeine. Does it sort of taste like flavored bath water? A little. Try putting a raw sugar in it or flavoring for more zing. We most went because this pink and green paradise is too adorable to not try and instagram.

New York's hottest clubs are in the meat packing district (this is not true at all but I really wanted to make that SNL joke). However, I did really enjoy galavanting around this area of New York. Okay...I cannot remember the name of this spot we went to at all. No matter how many variations in Google that I wrote "bar, across from Highline, big tree, rooftop, & sticky floors" I could not from photos find this place. And I wasn't even that drunk guys I promise!!

Anyways, some cool places to drink in this area are the Woodstock, The Standard Biergarten, & Brass Monkey which I'm not thinking is the bar we went to...the world may never know. More to come on places to go out, as I haven't really done the whole "club" scene in New York and can only imagine what it's like after meeting a group of NY financial advisors during Yacht Week.

Looking for a classy establishment to drink and make all waiters potentially hate you in a $30 dress waltzing around like you own the place (true story)? The Polo Bar is a blast to visit and pretend like you have money. This is Ralph Lauren's Bar, so make reservations beforehand as it can get crowded if you want to get a bite to eat while you are there. It is seriously a cool experience and everyone is dressed head to toe like they are about to mount a horse.

New York is also known for its rooftop and seaside bars, which I would highly take advantage of in the perfect fall months. The Watermark Bar, The Pod 39 Hotel Bar, & Gallow Green are a few to sip up from the top.

What Do I Do

Brooklyn Bridge

If you going to the One World Trade Center, this is a close stop nearby. Historically and architecturally, the Brooklyn Bridge is fun to walk across and see the separation between Brooklyn & Manhattan in this majestic piece of history.

The Highline

Located in the Meatpacking District, the Highline actually used to be a railroad that was turned into an environmentally friendly art collective and now boasts shops, restaurants and local artisans. A fun place to walk around and snag local trinkets!

Central Park/The Boathouse

Central Park is a place I could walk through every day and never really get tired of. If you go at the right time of fall, all the green trees will be starting to change to a colorful yellow, orange & red and there is truly so much to do in this part of the city. Between the multitude of ponds, places to picnic, local street food, parks, & of course the Boathouse you really could spend an entire day here. On a whim, Kelsey and I decided it would be a great idea to do a romantic rowboat through central park and honestly it was a fun perspective of the park itself. Although mostly couples surrounding us, we had a blast exploring different nooks and crannies of this landmark via boat. You can rent a boat for $15 p/h, incredibly cheap!

The Empire State Building

Okay ya'll, this is not an overrated experience in the slightest. It is a little costly, but nothing really beats this view at sunset. Going atop the empire state building is truly the best way to experience the city from above, and a 365 view to boot!

Again, there are a million things to do in New York City that I will be posting about in the future, but for now, a respectively "small" list if you will of how to condense this amazing city into one weekend.

Have more local recs? Italian spots? Comment below.



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