Spend a day strolling through the brownstone lined streets of the Upper West Side and you may feel like you have left NYC altogether. Heading uptown is almost like a vacation from the busyness of Midtown, and the pulsing life of downtown. The neighborhood is affluent, but laid back. Family friendly, cultured, and filled with fantastic food. This is the neighborhood where the cast of Seinfeld bickered over coffee, where Sally made her famous plea to Harry, and the place John Lennon called home.

What exactly is the Upper West Side?

It’s a neighborhood of Manhattan that goes from 59th Street up to 110th Street. It is bordered by Central Park on one side and the Hudson River on the other. The neighborhood is known for its laid-back vibe and is very family friendly.

Sounds good. Why should I spend time exploring it?

The Upper West Side has everything you could want in a Manhattan neighborhood: culture, history, fantastic food, open spaces, and nightlife. Whether you are traveling on your own, with friends, as a couple, or with kids there are things to do that will please everyone. It is also is home to tons of celebrities, and is a popular place for filming locations. Spend a day walking around this neighborhood, and it is quite possible you will stumble into a famous face or get to watch a show being filmed.

I am particularly fond of this neighborhood, as I used to live here and spent a lot of time exploring all the things that make it so special. This one day itinerary for the upper west side takes you through a full day of eating and exploring. If your schedule only allows for a part of the day, there is always a subway station within easy reach to head to a different part of the city.

Things to Know About this Itinerary

  • Walking around the city is the best way to explore it, so this itinerary has a lot of walking. It is easy to take cabs or hop on the subway more frequently if you aren’t interested in so much walking.
  • 20 City blocks = 1 mile
  • If you know the city well, this itinerary hits a lot of spots you have probably already been. If you are looking for some new things to see check out 7 secret spots in the Upper West Side.

For those feeling adventurous, start your morning extra early and go catch a taping of Live with Kelly and Michael. Take the 2 or 3 train to 66th street. Walk one block up. The studio is on the corner of Columbus and 67th.

9am – Live with Kelly and Michael Studio Taping

My friend Bonnie posing on the set - this was back in the days of Regis and Kelly!

My friend Bonnie posing on the set – this was back in the days of Regis and Kelly!

If you know when you will be in the city, you can request tickets, however I have seen the show five times and it has always been through standby. Get to the studio at 6am. Yes, 6am. The website suggests you should start lining up at 7am, but I guarantee the line will already be too long. Bring some coffee, and treats to share (you will be very popular) and a book or something to listen to. The wait goes by pretty quickly.

At 7:30/7:45 they will come out and give out tickets to the people who are able to get in. Even if you aren’t a fan of the show, it is quite fun to attend, lots of energy, and much smaller than what it looks like on TV.

  • For the GPS:  7 Lincoln Square, New York, NY 10023

Now it is time to get some food! Walk up Columbus Avenue to 72nd Street. Turn left, your breakfast stop is about halfway down the street. (If you didn’t go see Kelly and Michael, this is where your day begins! Take the 1,2 or 3 subway to 72nd and Broadway.) ~6 minutes

10:30am – Breakfast at 72nd Street Bagel

When it comes to bagels in NYC, you really can’t go wrong. But this is one of my favorite bagel places in the city. Order the bacon, egg and cheese on an everything bagel. Squeeze yourself into one of the tiny tables and enjoy a classic and delicious NYC breakfast.

  • For the GPS: 130 W. 72nd Street

Walk straight across 72nd Street (back the way you came) toward Central Park. If you cross Broadway, you went the wrong way, turn around! Cross over Columbus and you will see Central Park in front you. As you reach the corner, be sure to take a photo of The Dakota. This is Manhattan’s first luxury apartment building, and is famous for the many celebrities who have lived (and still live) here. It is also where John Lennon was shot. Walk into the park from 72nd street and go straight. ~ 5 minutes

11:15am – Central Park

A Walking trail through Central Park

photo by m01229 via Flickr Creative Commons

An entire day can be spent exploring this space of the city. There are an incredible number of things to do here and in no way could I cover them all. Since this is an itinerary of the Upper West Side, we will stick to a small portion of the park today.

From 72nd Street, walk past all the guys trying to take you on a rickshaw ride, and onto a path straight ahead. This leads you Strawberry Fields and the Imagine Circle, a quiet area dedicated to John Lennon.

From here follow the path down and onto the main track. Depending on the time of year, this road will be filled with bikers, runners and (roller)bladers. The lake will be on your right hand side and is a lovely place to stroll along, sit and people watch. I love watching the dog walkers in Central Park, they are amazing! I can barely control one dog on a leash, and these professionals have 6-12 dogs!

Continue following the lake. Explore the nooks and crannies and the hidden pathways around it. Keep walking north and you will eventually come to the 79th Street Transverse. This is a road that cuts through the park from east to west, so there will be cars and taxis here. Stay on the path, cross over the transverse, and bear to the right at the first fork after crossing.

Detour–>The first thing you will come across is the Swedish Cottage Marionette Theater. It is a rustic cottage and often has events for kids. If you are traveling with kids, it is worth checking out the schedule ahead of time to see if anything is happening.
Belvedere Castle

photo by Dmytro Kochetov via Flickr Creative Commons

Next to the theater you will see the entrance to the Shakespeare Garden. A peaceful garden filled only with flowers mentioned in Shakespeare’s plays. This is a romantic and quiet section of the park, and a great place to sit and relax. It is especially captivating in the spring when everything is in bloom. The Shakespeare Theater (where Shakespeare in the park happens) is nearby if you want to go check it out.

From here, follow the footpath out of the garden – it will lead you right to Belvedere Castle. Climb the tower and see views of the Great Lawn and Turtle Pond. Inside the castle there are historic and natural artifacts to check out if you are so inclined.

Total amount of walking from Strawberry Fields to Belvedere Castle is about ½ mile, depending on how much exploring of the path’s you do.

If you want a full walking tour of the park check out Free Tours By Foot.

From Belvedere Castle walk back the way you came and follow the path back the way you came (west) cross the 79th street transverse until you see a path that leads you out of the park and back to Central Park West. You will see the Museum through the trees. ~7 minutes

If you are hungry, grab a pretzel, hotdog or nuts from one of the street vendors outside the museum before going in.

12:30pm – Museum of Natural History

Outside of the the Building of Museum of Natural History

photo by Steveen Manon via Flickr Creative Commons

The Museum of Natural History is one of the best museums in NYC. I find museums boring, so I don’t typically include them in an itinerary, but I always make an exception for the Museum of Natural History. The exhibits (and 32 million objects) make you feel like a kid; marveling at huge fossils, and traveling around the world to see how people used to live.

You could easily spend the whole day here, and in no way will you even make a dent in the museum in just a few hours. Do your research beforehand – decide what interests you and what you really want to see.  Check out the website for a self guided tour and arrive with a plan! 

Exit the museum and head west on 81st street. Cross over Columbus and Amsterdam, then turn left. The restaurant is between 81st and 80th streets on Amsterdam. ~5 minutes

3pm – Lunch at Island Burgers and Shakes

Skip the Shake Shack right outside the museum (there are plenty around the city if you really want to eat here) and head to Island Burgers and Shakes for some of the best burgers on the Upper West Side. Going after the lunch rush is the best option, as it is a small restaurant. The portions are huge and prices are reasonable, which only amplifies the deliciousness of the burgers. Choose from a variety of decadent burgers or make your own.

  • For the GPS: 422 Amsterdam Ave.

It’s time to stretch a bit after that filling lunch! The best way is to take a  stroll through the streets of the UWS. Walk back the way you came, across Amsterdam and turn onto Columbus Ave. This street has many cute boutique shops to pop into. If shopping isn’t your thing, it is just a great street to feel the pulse of the UWS.

4pm – Walk Down Columbus Avenue

A walk down Columbus Ave gives you a glimpse into the stylish charm that makes the UWS special. From clothing shops to toy stores to thrift shops, there are a wide range of places to check out.

  • If it is a Sunday, be sure to stop at the Green Flea at Middle School 44 on 77th Street. It is a haven for thrift shopping and finding one of a kind handmade items.
  • Magnolia cupcakes is on Columbus between 70th and 69th. Stop here if you are craving a moist and sweet cupcake.
  • Lincoln Center is on 64th street and worth a spin around

Walk all the way down Columbus Ave to 59th Street. This is Columbus Circle.

5:00pm – Columbus Circle

Columbus Circle from Above

photo by Andrew Dallos via Flickr Creative Commons

This is a pretty sweet spot in the city. It is the only traffic circle, and is the intersection of 8th Ave, Broadway, Central Park West and Central Park South. It’s not worth sticking around for too long, but is a good place to move on from the UWS to another part of the city as there are various subway lines that connect here. It’s also a quick stroll to midtown or Hell’s Kitchen if that is where you are headed next.

If you are planning on sticking around the UWS (which you should as there is more to do!), head into the Time Warner Building to the Shops at Columbus Circle. Take the escalators up to get a view of Columbus Circle and Central Park.

When you are done exploring Columbus Circle, it is time for some well deserved drinks. Head up Broadway 7 blocks to 66th street and turn left. Cross Amsterdam and West End and turn right onto Riverside Blvd. When you come to 68th street, enter the park and walk down the long incline pathway. You will see the green umbrellas of the Pier I Cafe. ~20 minutes

6:00pm – Drinks at Pier I Cafe

Sunset over the Hudson River

photo by Dan Nguyen via Flickr Creative Commons

From May to September, the best spot on the UWS to have some happy hour drinks is at Pier I Cafe. It’s an open air eatery next to the Hudson River and under the West Side Highway. Choose a beer from the all New York beer draft menu, find a table, and watch as the sun dips down below the Hudson. It’s clean, there is a great vibe, though it will be crowded, so if you see a table – grab it!

If you are visiting from October to April, I would grab drinks at the Empire Hotel (right across from Lincoln Center on 63rd Street).

  • For the GPS: 500 W. 70th Street

8:00pm – Dinner

It is hard for me to pick a place to eat dinner, there are so many places to choose from. It also completely depends on your mood – what are you interested in eating? Pizza? Chinese? Greek? Do you want fancy or quick? You can find all of these options on the UWS.

I have a million recommendations but one restaurant that kind-of-sort-of fits into all those categories is Nice Matin. It is a semi-casual french bistro, that has a wide selection of dishes. My friend used to waitress here so often parked it at a table for brunch, lunch and dinner! Celebrities also tend to frequent this place, it is easy to hide in the back table. My friend used to text me all of the time with the comings and goings of the UWS celebs!

Nice Matin is located on the corner of Amsterdam and 79th. It is a 15 minute walk from Pier I Cafe.

Wherever you choose to eat on the UWS, end your night with some of the best cookies in the city on 74th and Amsterdam.

10pm – Levain Bakery for Chocolate Chip Cookies

chocolate chip cookies from Levain Bakery

photo by Angela N. via Flickr Creative Commons

Strolling around the upper west side and not stopping at Levain Bakery for an orgasm inducing chocolate chip cookie is a big mistake. This bakery is popular and written about left and right, but for good reason. The thick chocolate chip cookies are rich, sweet and doughy and oozing with chocolate.

  • For the GPS: 167 W. 74th St.

From Levain Bakery, walk down two blocks to 72nd street and hop on the 1,2 or 3 train back to wherever you need to go.

If you follow this itinerary walking from place to place it should result in about 1 hour and 40 minutes of walking, and 5 miles. Of course this doesn’t factor in meandering around the parks, walking through the museum, or stairs in buildings. Overall, it’s a solid itinerary that covers many of the things to do in the Upper West Side.