Self-Guided Upper West Side Walking Tour - The Adventuring Millennial

Welcome to the Upper West Side (UWS) in the NYC borough of Manhattan. This neighborhood sits between Central Park and Riverside Park and stretches from 59th to 110th Street.

It is filled with culture, history, and (like most of Manhattan) money. The UWS is one of the wealthiest neighborhoods in the city. The average UWS 1-bedroom rents for almost $4,000.

Many visitors recognize the UWS from TV shows and movies. You’ve Got Mail, Seinfeld, and The Marvelous Mrs. Maisel were all filmed here. The brownstone-lined streets, towering Central Park West residences and historic restaurants make this an iconic neighborhood.

Since the UWS is such a large neighborhood, it can be hard to fit everything into one walking tour. So, I created a shorter walking tour that covers the middle section of the neighborhood. This tour will take us from the Museum of Natural History at 79st Street down to the Lincoln Center at 66th Street. I’ve taken plenty of walking tours during my travels. I always enjoy learning more about a city’s history and culture. But, as a budget traveler, it can be hard to pay for these tours in every city. Instead, I’ve started taking self-guided walking tours. These are an affordable way to explore a city at my own pace.

My Self-Guided Upper West Side Walking Tour is designed to last anywhere from a few hours to a full day. Spend your time leisurely exploring the museums, cafes, and parks highlighted in this tour. Or, use this as a guide to maximize a short amount of time in the UWS. Either way, explore at your own pace and have fun!

Start: American Museum of Natural History

Central Park West & 79th St

To start our tour, take the B or C trains uptown to 81st Street-Museum of Natural History or the 1 train to 81st (on Broadway). If you take the 1 train, walk from Broadway towards Central Park to get to the corner of Central Park West & 79th Street.

We will start at the American Museum of Natural History. This impressive museum first opened in 1877. Theodore Roosevelt’s father was one of the museum’s founders. At this museum, you can see an expansive collection of fossils, natural dioramas, and cultural artifacts.

If you purchase your ticket at the counter, you can pay any amount. Yes, you can even pay $1 to visit the museum. So, before starting our walking tour, you might want to spend some time exploring this museum.

The Macy’s Thanksgiving Day Parade kicks off every year near the American Museum of Natural History. Look at the sidewalk at the corner of 77th and Central Park West to find a plaque commemorating the starting point. If you are in NYC over Thanksgiving, stop by the day before the parade to watch the balloon inflation. This is a fun lower-key event (than the actual parade) where you can watch the balloons being filled with air in preparation for the big event.

At this point, you are also close to the New-York Historical Society. Keep an eye out for their unique rotating exhibits. From the end of 2018-early 2019, this museum featured the Harry Potter: A History of Magic traveling exhibit. Unlike the American Museum of Natural History, this museum charges a standard ticket price of $21 for adults. Some exhibits cost an additional fee.

Outside the American Museum of Natural History, you can find one of my favorite NYC food carts, Wafels & Dinges. It is open from 8am-sunset. Stop by for a sweet or savory treat before starting our tour.

From here, we are going to walk to Zabar’s. Walk along 80th street away from Central Park.

Stop 1: Zabar’s

2245 Broadway (80th and Broadway)

As you walk along 80th Street towards Zabar’s, you will pass Sarabeth’s at the corner of 80th and Amsterdam. This neighborhood favorite has been in the UWS for almost 30 years. It is a popular brunch spot, so you may want to add it to your weekend plans.

Zabar’s is a neighborhood institution. This specialty grocery store first opened in 1934. They started as a modest grocer and coffee shop. Now, 80 years later, Zabar’s spans almost the entire block. It is a massive grocery store filled with deli meat, smoked fish, bagels, and other NY classics.

Zabar’s was featured in the movies You’ve Got Mail and Manhattan.

If you aren’t from NY, be prepared before entering Zabar’s. NYC grocery stores are crowded and cramped. And people can get…easily frustrated if you are in their way. Try to be patient and embrace the true New York experience. Don’t let this keep you from checking out the store. This is a great place to grab an authentic New York bagel topped with smoked fish.

After you check out, we are going to keep heading West towards Riverside Park. Walk about 5 minutes along 80th or 79th street, and you should reach the park.

Stop 2: Riverside Park

If you are thinking of parks in the UWS, Central Park might be the first one you think of. But Riverside Park shouldn’t be ignored. This park sits between the Hudson River and Riverside Drive. It stretches from 72nd street up to 125th. If you want to spend the rest of your time exploring this park, consider trekking up to 122nd to see Grant’s Tomb. (This is the burial place & monument honoring the 18th U.S. President Ulysses S. Grant).

For now, we are going to continue south in the park. We are making our way to the bottom of the park (72nd Street). There is a nice walking trail through this park, so enjoy this as a quiet escape from the city streets.

You may recognize this park from TV or films. It has been featured in 30 Rock, Friends, Seinfeld, The Marvelous Mrs. Maisel, and You’ve Got Mail.

This park was first designed by Fredrick Law Olmsted (the designer of Central Park) in the late 1800s. Before its completion, other designers modified his design to create the park we know today. But, they kept Olmsted’s original plan for a park that curved along the river.

Keep walking south until you reach 72nd Street. Once you get here, you should find the Elenor Roosevelt Statue near the exit of Riverside Park.

Stop 3: Eleanor Roosevelt Memorial

Riverside Drive and 72 Street (just inside Riverside Park)

At the end of Riverside Park, you will reach the Eleanor Roosevelt Memorial. Eleanor Roosevelt was an American diplomat, activist, and delegate to the United Nations. She was the wife of the 32nd U.S. President Franklin D. Roosevelt. She is the longest-serving First Lady (1933-1945).

Although now she is widely celebrated, she was controversial during her time. She was outspoken and held radical opinions. She held regular press conferences and contributed to a newspaper column. Even after FDR’s passing, she continued to maintain an active political career.

This monument was dedicated in 1996, with Hillary Clinton giving the dedication speech. It is the first monument recognizing a U.S. First Lady.

Next, we are heading to the BEST bakery in the UWS. Get your stomachs ready. Head east along 72nd Street until you reach Amsterdam Ave. Turn left onto Amsterdam. At the corner of 74th and Amsterdam, you will see Levain Bakery.

Stop 4: Levain Bakery

167 W 74th St (74th & Amsterdam Ave)

Even if you are not ready for a sweet, pick up something from Levain Bakery for later. You will thank me, I promise.

Levain’s softball-sized cookies are the stuff of legends. I didn’t understand what my life was missing until I tried my first Levain cookie. Now, I’m hooked.

Levain opened in 1994 and this bakery has been drawing recognition ever since. Celebs like Taylor Swift and Kristin Chenoweth obsess over this bakery. Oprah even featured Levain’s Raisin Sticky Buns on her show.

This place frequently appears on Must Eat lists. And with good reason, seriously, these cookies are softball sized. Did you catch that earlier? These huge cookies are slightly crisp on the outside but warm and chewy on the inside. So. Perfect.

I recommend the Dark Chocolate Peanut Butter Chip cookie. But, their classic Chocolate Chip Walnut cookie is a crowd pleaser.

After you grab a treat (or 2), we are heading to our next stop. Head east on 74th Street until you reach Columbus. Turn right on Columbus until you reach 73rd Street. Turn left on 73rd Street. The Dakota will be just ahead, before you reach Central Park.

Stop 5: The Dakota

1 W 72nd Street (72nd Street & Central Park West)

The Dakota is the most famous apartment building in the UWS. John Lennon lived here until 1980, when he was tragically murdered outside the building.

The building was constructed between 1880-1884. It was ironically named The Dakota in reference to the Dakota Territory. During the 1880s, this area of Manhattan was pretty empty, reminding the builders of the large, open area in Middle America (oh, how times have changed).

The Dakota was made a National Historic Landmark in 1976. Over the years, a few famous faces have lived in this building including Judy Garland, Rosie O’Donnell, and John Madden. The building’s exterior was also featured in the classic horror film Rosemary’s Baby.

From here, we are going to walk across the street and enter Central Park. We are going to visit Strawberry Fields, the memorial dedicated to John Lennon. Enter Central Park at 72nd Street. Once in the park, walk straight for about a minute (you will be on a sidewalk along a “main road”) Once you reach the fork, turn left. You should see signs for Strawberry Fields. Turn right to follow the signs. You should soon enter the small, quiet memorial.

Stop 6: Strawberry Fields

Strawberry Fields is a small area of Central Park dedicated to the memory of John Lennon, who was murdered outside The Dakota in 1980. The memorial was dedicated in 1985 by Lennon’s widow Yoko Ono and the New York Mayor at the time, Ed Koch.

This memorial features a circular mosaic with the word Imagine in the center. It is supposed to be a quiet, serene area, but it is often filled with the sounds of a busker performing their rendition of a Beatles song. Tourists love to crowd around the circle and take an Instagram-worthy pic next to the memorial.

After you’ve paid your respects, taken your pics, or purchased a trinket, let’s move on. Our next stop is Tavern on the Green. You can head back the way you came and exit Central Park. Walk south along Central Park West until you reach 67th Street. Or, stay in Central Park and wander down. There are a few different paths you could take, but if you follow the main road (filled with runners and bikers) you will reach Tavern on the Green after about 10 minutes.

Stop 7: Tavern on the Green

Central Park, W 67th Street

You’ve reached another iconic UWS eatery. Tavern on the Green first opened as a restaurant in 1934. Before then, the building served as a sheepfold. Do you see the large open field in the middle of Central Park across from the restaurant? You are looking at Sheep’s Meadow. Yes, sheep actually used to graze here. Now, it is a popular picnicking and sunbathing spot for locals during the summer months.

Tavern on the Green has changed owners a few times over the years. It was a restaurant from 1934-2009. After 2009, the building was used as a gift shop and visitor’s center. In 2014, Tavern on the Green was reopened (to the delight of locals and tourists).

If you are looking for a nice meal, book a reservation at Tavern on the Green. My husband and I celebrated our 3rd wedding anniversary with a nice dinner on the outdoor patio. The low string lights added a romantic ambiance to the meal. And the free celebratory slice of cake didn’t hurt my feelings!

If you want to spend more time in Central Park, consider checking out my Central Park Walking Tour. This tour ends at Sheep’s Meadow, so you could follow it in reverse from here.

Or, if you are ready to keep going, we are going to walk to our final stop. Head east and exit Central Park at 67th Street. Continue south until you reach 66th Street. Turn right on 66th Street. Walk until you reach Columbus. Turn left on Columbus. Then, turn right onto 65th Street. Soon, you will reach The Juilliard School.

Stop 8: The Juilliard School

60 Lincoln Center Plaza (Broadway & 65th Street)

You’ve reached the last stop on our tour, Juilliard. This is the famous performing arts school that trains students in dance, drama, music and other arts. Robin Williams, Yo-Yo Ma, and Jessica Chastain are just three of the hundreds of notable Juilliard alumni.

Juilliard started in 1905 as a small musical institute and has grown to be one of the most prestigious art schools in the world. The acceptance rate is just around 7%.

While you are in the area, stop by the Lincoln Center. This is a performing arts complex that is home to the New York Philharmonic, New York City Ballet, New York City Opera and Metropolitan Opera. In the 1950s, John D. Rockefeller III helped fund and revitalize the Lincoln Center.

You could also stop by the Folk Art Museum. This small museum, located at 66th Street and Columbus Ave, features work by self-taught artists. It is free to visit, so check their website to learn more about the current exhibits.

Another option is to check out the TKTS Booth. Most tourists are familiar with the location in Times Square. But, you can also check out their Lincoln Center location inside the David Rubenstein Atrium at 62nd and Columbus Ave. This booth sells discounted Broadway and Off-Broadway tickets. The Lincoln Center booth opens at noon daily, but people often line up at least an hour early. I’ve managed to score a few deals at this booth, so if you are looking for cheap same-day Broadway tickets, you may want to stop by.

If you are looking for some food or drinks, there are a few great options in the area:

P.J. Clarke’s- Legendary saloon that opened in 1884 and serves a dang good burger
The Smith– Classic American eatery with a killer brunch
Joe Coffee– Family-ownded roastery with locations scattered throughout the city

We’ve reached the end of our tour. I hope you enjoyed exploring the Upper West Side. You can spend some more time in the area or hop on the subway and head to your next adventure. Juilliard is right next to the 66th Street station on the 1 Line. Or, continue down to 59th Street (Columbus Circle) where you can catch the 1, 2, A, B, C or D trains.