The Upper West Side was the first neighborhood I lived in when I moved to New York at 18. 

I was attending an acting conservatory in the neighborhood, so ended up living in student housing at The Stratford Arms on 70th and Broadway. 

The building was famously the hotel that Holden Caulfield had stayed in during his city adventure in Catcher in the Rye. Naturally, I assumed it’d be a pretty nice place to live.

Turns out living in that building was going to be my first adventure. 

About a day after my parents dropped me off, I learned that the school had bought this historic building from a group that had been using it as a halfway house. 

Part of the terms of the purchase was that the halfway house residents got to basically live out their lives there. Needless to say, I have a ton of bizarre stories from my years living there. 

I also have many memories of running around the neighborhood with the schoolmates, who would quickly become some of my best friends. 

I grew so much in my two years living on the Upper West Side. It will always have a very special place in my heart. 

Recently I booked a trip home to New York for this summer, and I can guarantee the UWS is a neighborhood where I’ll be spending a lot of time. 

If you want to explore some of my favorite things about the area, follow my guide to the best things to do on the Upper West Side. 

1. Relax in Riverside Park

Have you ever seen the film You’ve Got Mail?

If you have, then (spoiler alert!) you’ll instantly recognize this as the park where Meg Ryan and Tom Hanks reunite at the end.

You’ll find Riverside Park is a quiet neighborhood park. It runs along the Hudson River from 72nd Street to 158th street.

Local’s Tip: If you visit in the summer, keep an eye out for the goats they keep around to maintain the grass. 

2. Attend the Ballet

Seeing the New York City Ballet perform is a serious treat. Watching them dance is like stepping into a dream.

If you’ve never been to the ballet before, Lincoln Center is the place to give it a go. You’ll be watching some of the best ballerinas in the country perform. 

You must catch The Nutcracker if you’re in town during the holidays. It’s one of their most beloved shows and a true Christmas classic. 

3. Listen to the Symphony

Another one of my favorite Lincoln Center activities is catching a performance of the NY Philharmonic Orchestra.

Ever since catching my first show here a few years ago, I try to see a show here at least once a year. 

This is another once-in-a-lifetime opportunity to see the best musicians play together under one roof.

4. See a Show at the Beacon

Catching a show at the Beacon Theater has been on my bucket list for a while now. 

This small theater has an intimate feel and outstanding acoustics giving it the ability to draw some pretty big names here like Bob Dylan and Jerry Seinfeld.

Keep an out on their schedule and book your tickets early!

5. Hang in Central Park

A large majority of my favorite NYC memories take place in Central Park.

Scoring tickets to Shakespeare in the Park and having a sunset picnic in front of Belvedere Castle is at the top of my list for when I’m home later this summer. 

If you haven’t been to the park before, also check out Bethesda Terrace, Strawberry Fields, and Tavern on the Green while you’re on the west side of the park. 

Don’t feel like walking around the park? Book one of these tours instead!

6. Dance at Midsummer Night Swing

Midsummer Night Swing is one of the hottest summer dance parties on the UWS. There’s always a theme to the evening, plus live music and dance lessons from the performers.

They held the evenings in Damrosch Park, which is right behind the ballet building.

This is a seriously unique city event that I’m ashamed to say is still on my bucket list. Friends who have gone have raved about what a marvelous time this event is.

But like everything in the city, you’ll want to book your tickets well ahead of time.

7. Hit Up the Grand Bazaar

Every Sunday on 77th and Amsterdam you’ll find fantastic shopping at the Grand Bazaar

When I was living in the neighborhood, I used to love grabbing an iced latte and strolling around this place. 

You’ll see everything from antiques, furniture, to unique designers and artisanal food booths. 

The market operates year-round, making it an easy choice any afternoon.

8. See a Show at The Vivian Beaumont

One of my all-time favorite things about the city is how many performing arts venues there are. 

The UWS has one theater in particular that I really love catching shows at, The Vivian Beaumont

It’s run by Lincoln Center and has a habit of reviving gorgeous classics like South Pacific, My Fair Lady, and The King and I.

Plus it brings new hits to the city, like War Horse, Oslo, and Ann.

The shows here are popular with locals, so book early!

9. Listen to Some Jazz

The UWS may not have as many jazz spots as the village, but it has some solid choices.

These are some of my favorite spots to listen to jazz on the Upper West Side:

10. Grab a Drink on a Rooftop

Another thing that I’m looking forward to on my return home is spending some quality time chilling on rooftops.

The UWS has a ton of great options if you’re looking for a way to cool off during the summer. These are the rooftops that I can’t wait to hang out at again:

11. Check Out New York Historical Society

You’ll find the New York Historical Society along a gorgeous stretch of Central Park West. 

It’s both a library and a museum and a unique little neighborhood spot.

Their special exhibits are always epic. I saw one they did on Harry Potter and another on Madeline that were both marvelous. 

The museum is fairly small, so I’d say only pay admission if there’s an exhibit that you’re dying to see.

12. Visit the American Museum of Natural History

Want to check out some epic dinosaur bones and rocks from space?

Then you’ll want to head down the street from the NYHS, to the American Museum of Natural History

This is one museum you’ll want to plan on spending the entire morning or afternoon exploring. 

Don’t forget to check out the giant blue whale and the Hayden Planetarium while you’re there. Those are some of my favorite parts of the museum. 

Plan ahead by booking one of these awesome tours of the museum!

13. Go on a Dessert Tour

After living in the neighborhood for two years, I think I’ve been to every bakery and cafe around sampling their desserts.

Typically, when I find myself in the neighborhood, I always swing by one of two of these spots for a sweet treat:

14. Laugh at the West Side Comedy Club

A short walk from Levain Bakery you’ll find the West Side Comedy Club.

I always associate the two, because I can’t help but grab a cookie or two before I catch a show.

The club is intimate and the comedians are typically hilarious. 

They also have a delicious Mexican menu and equally yummy cocktails. I always go for either the guacamole or sriracha fries with a margarita. 

15. Grab an Epic Meal

The UWS has some of my favorite restaurants in the city. 

When I was in school I would treat myself to dinner out once or twice a week.

I’ve spent countless hours at some of these spots learning lines and catching up with friends.

I still love planning nights out over here so that I can hit up some of my favorite dining spots.

If you’re looking for a knock-out meal, make reservations at one of these UWS gems:

16. Shop at Columbus Circle

Swinging by the Shops at Columbus Circle is always a welcome treat. 

They’ve got plenty of basic shops like J. Crew and Lululemon to classics like Stuart Weitzman and Ted Baker.

It’s also a substantial area to grab a quick snack or coffee before hitting up the park.

Tartinery has a great cafe if you’re in search of a proper sit-down lunch.

Local’s Tip: Stop by the Whole Foods on the bottom level to pick up all of your picnic needs!

17. Enjoy Afternoon Tea

Another one of my favorite city activities is going out for an afternoon tea with friends at Alice’s Tea Cup on the UWS.

Alice’s has been my neighborhood go-to anytime I’m craving tea and scones. They also make delicious crepes!

This spot is Alice in Wonderland themed and absolutely adorable. They even have little fairy wings for kids to wear as they brunch.

It gets quite hectic on the weekends, so I typically get a tea and a scone or two to go with some extra clotted cream.

Then take my goodies to the park to enjoy on a bench while I read. 

18. Check Out the American Folk Art Museum

If you’re wondering what is on display at a folk art museum, let me fill you in.

At the American Folk Art Museum, you’ll see things like quilts, drawings, and sculptures.

I love checking out their gift shop. They always have unique gifts for my friends who love crafts. 

The museum is fairly small and free to enter, so it’s an easy decision to visit.

19. Visit Grant’s Tomb

Did you know the Upper West Side has one of the biggest mausoleums in North America?

General Grant’s Tomb is a seriously impressive historical stop while you’re uptown.

If you really want to explore and learn a bit of the history, set up a free tour of the mausoleum.

20. Grab an Authentic Bagel and Smear

The Upper West Side has a very strong history with bagels and smear.

If you’re looking for an authentic NY bagel, this is the neighborhood to hit up.

Both Zabar’s and Barney Greengrass serve up some of the best bagels around. 

Grabbing a bite at either place will be a brilliant decision!

21. Appreciate the Architecture

This neighborhood has some of the best architecture in the city. 

If you love wandering around staring at old buildings, these are the spots you’ll want to check out:

22. Visit the Nicholas Roerich Museum

Nicholas Roerich is a Russian-born artist whose paintings focus on the great outdoors, specifically the Himalayas.

His art has a bit of a spiritual vibe to it and is overall relaxing to wander around looking at. Plus, you’ll also spot artifacts from all of his travels. 

The entire experience feels really intimate and the staff are all super helpful.

You’ll find this small museum inside a brownstone at 319 West 107th Street.

It’s free to visit the Nicholas Roerich Museum, though they encourage donations. 

23. Hit Up a Bar

Since I went to school in this neighborhood, I think it’s safe to say I’ve hit up a lot of the bars in this neighborhood.

These are some of my go-to Upper West Side bars:

24. See a Movie

Even when I was living on the Upper East Side, I would always plan on catching films on the UWS because they have some of the best movie theaters in uptown Manhattan.

I would take great joy in grabbing a coffee and strolling across Central Park to catch the latest indie film or big budget hit at one of these theaters:

Wrapping It Up

After writing this, one thing is certain—my return to NYC cannot come soon enough!

I’m already having dreams of Zabars bagels, park picnics, and of course Shakespeare in the Park

Let me know in the comments below what you’re most looking forward to checking out the next time you’re on the Upper West Side. 

Check out some of these popular tours while you’re on New York’s Upper West Side!


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