Upper East Side
- Physical DifficultyThis is the average user-submitted rating on the physical difficulty of this route. In general, green is beginner, blue is intermediate, black is advanced/most difficult and double-black is expert-only. It is recommended that users build up to black and double-black routes.
- Technical DifficultyThis is the average user-submitted rating on the technical difficulty of this route. In general, green is beginner, blue is intermediate, black is advanced/most difficult and double-black is expert-only. It is recommended that users build up to black and double-black routes.
This NYC walk takes you through one of NYC’s most exclusive neighborhoods, the Upper East Side. The Upper East Side is home to the city’s top museums, many of which are conveniently located on Museum Mile, as well as more shopping than one could do in a year from luxury upscale shops on Madison Avenue to brand name budget chains and secondhand shops specializing in designer digs. You’ll find a vast variety of eating here from the world’s most expensive dessert to a quick burger to go. We’ll also take you through some lovely respites from the hectic city life such as Gracie Mansion and the FDR Four Freedoms Park, topped off with a tram ride over the East River and stunning skyline views.
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Route Description for Upper East Side
Start this route at the Central Park North subway station (lines 2 & 3). With Central Park ahead of you take a left onto Central Park North (you should be hugging the park on your right-hand side). We won’t explore this iconic city park on this route, but if you would like to, click here. Stay on this street for roughly 200 m, until you come to the corner of the park. Here there will be a fork. Stay to the right and then take a right onto 5th Avenue.
Continue on 5th Avenue for another 200 m as we begin to enter the Upper East Side. Once you pass 105th Street (it will intersect with 5th Avenue) you’re officially on Museum Mile. This stretch is home to some of NYC’s finest collections of art, design, history, and culture from all over the world. Between 105th and 106th Street, El Museo del Barrio will be on your left-hand side. Exhibits here are focused on Latino, predominantly Puerto Rican, art and culture.
One block further is the Museum of the City of New York. This historic museum was founded in 1923 and inside you’ll find more than 750,000 items from photos to prints, paintings, costumes and more, all aimed to give visitors a better understanding of the deep-rooted history of NYC. Some of the most popular exhibits include a man’s suit worn to George Washington’s Inaugural Ball, a large propaganda poster collection dating back to World War I, and a Stettheimer Dollhouse.
Continue about a 1.0 km down 5th Avenue. There aren’t many big sights in this section, so just enjoy the peaceful walk with beautiful Central Park to your right and some of NYC’s most exclusive real estate on your left. Between 93rd and 92nd Street is The Jewish Museum. Housed in the stunning historic Warburg mansion, this museum explores four thousand years of Jewish culture through more than 26,000 objects, fine arts, media, and more. As well, you can find works by Andy Warhol and Amedeo Modigliani.
Two blocks further, between 91st and 90th Street is the Cooper Hewitt, Smithsonian Design Museum. Dedicated to showcasing the history and culture of contemporary design and creativity through exhibitions such as “Please Be Seated” that showcased contemporary chairs. They also have a pleasant garden and café to enjoy a coffee on a warm sunny day!
Continue 100 m more for one of the most famous museums on this stretch, the Solomon R. Guggenheim Museum. Housed in the instantly recognizable building designed by architect Frank Lloyd Wright, the museum features a wide collection of Impressionist, Post-Impressionist, early modern, and contemporary art.
Stay on 5th Avenue for roughly another 150 m until you intersect with East 86th Street. Take a left here. On your right hand side will be the Neue Galerie, which houses collections from German and Austrian artists from the early 20th century such as Gustav Klimt, Kokoschka, and Egon Schiele.
We’ll stay on 86th Street for almost 2.0 km, on route to the picturesque Gracie Mansion. In addition to some of the city’s most expensive real estate, you’ll also pass a number of restaurants, cafes and shops. Right after you pass Lexington Avenue, for example, you’ll find Shake Shack; sprouting from a hot dog cart in Madison Square Park in 2004, this location has a lovely outdoor area away from the busy crowds on 86th Street. This budget-friendly fast food joint is growing at a rapid rate, known for serving 100% angus beef burgers without hormones or antibiotics.
If you’re looking for some delicious homemade baked goods continue about 200 m more to the corner of 2nd Avenue and 86th Street. You’ll find Two Little Red Hens serving absolutely mouthwatering, albeit pricey, cakes and treats. Stay on 86th Street for another 600 m or so, until you reach the Carl Schurz Park.
The park offers a lovely respite from the busy city streets and is also home to New York’s official mayoral residence since 1942. Built in 1799, Gracie Mansion is open for visitors with a prior reservation. In addition to the home, the surrounding park grounds are magnificent on a nice day, providing unbeatable views of the water, and the boisterous Hell Gate, the intersection of the East River, Harlem River and Long Island Sound.
Relax here for a bit, and then head out of the park, taking a left onto East End Avenue. When you hit East 82nd Street take a right. Follow this lovely residential street into the heart of the Upper East Side. This street is a bit quieter than 86th Street, but provides a nice transition after a relaxing stroll around Carl Schurz Park. You’ll stay on this route for about 2.0 km, heading back towards Central Park, until you intersect 5th Avenue. Again, there aren’t too many big sites to see, rather just the great ambiance.
Once you hit 5th Avenue, the Metropolitan Museum of Art will be directly ahead of you. This world-famous museum houses a permanent collection of more than 2 million works, spanning more than 5,000 years from cultures throughout the world. We definitely recommend taking some time to at least get a short impression of the museum.
When you exit the Met take a right onto 5th Avenue, your first left onto East 81st Street and then your second right onto Park Avenue. Stroll down Park for a 1.0 km, soaking in the atmosphere of one of NYC’s most exclusive addresses. When you run into East 72nd Street take a right and then your first left onto Madison Avenue.
You’re now entering one of the most prestigious shopping sections in all of New York City. The stretch from East 72nd to East 66th Street on Madison is home to a number of upscale fashion boutiques such as Prada, Chanel, Gucci, Cartier, Chloe and more. Perhaps pop in a shop here or maybe just save your (few thousand) pennies with a little window-shopping.
Stay on Madison for about 2.0 km, until you run into East 60th Street. Take a left here. This route has a number of lovely sidewalk cafes for a dose of caffeine, you’ve earned it after this long walk! Stay on 60th Street for almost a 1.0 km. After about 800 m Serendipity 3 will be on your left-hand side. This place is an icon of the Upper East Side, welcoming patrons such as Marilyn Monroe, Andy Warhol, and Jackie O. It was made even more famous when the restaurant introduced the Golden Opulence Sundae, the world’s most expensive dessert at a hefty price tag of $1,000.
Continue on 60th about 50 m further until the Roosevelt Island Tramway is on your right side. Hop on the tram here, for the cost of a subway ride you get to experience stunning views of the city skyline, both Manhattan and Brooklyn. Get off onto Roosevelt Island. Historically, this area was closed off to the public, but has since become a small residential community that’s really nice to explore.
The entire island is about 3.0 km long, so if you’re feeling energetic, head down Main Street towards the north. This is the more developed section of the island, stretching more than 2.0 km until it reaches a point in the center of the East River.
If you’re tired after this already long walk, just head south on West Loop Road, towards the Franklin D. Roosevelt Four Freedoms Park. Here you’ll find not only spectacular views of the Manhattan skyline but impressive works by world-renowned artists such as architect Louis Kahn and sculptor Jo Davidson.
Spend some time here enjoying the beautiful scenery. Head back the way you came and hop back on the tramway. Once you’re back in Manhattan you can easily connect to a number of points throughout the city at the 59th Street Lexington Avenue subway station.
Insider Hints for Upper East Side
- This walk is long – start early, pack water and a light jacket.
- Check out which museums offer free admission all the time or on specific days and times (for example, the Museum of the City of New York is always “pay what you want”, the Neue Galerie is free on the first Friday of each month from 6 to 8PM, The Jewish Museum on Saturdays, the Solomon R. Guggenheim Museum on Saturdays from 5:45 to 7:45PM, and El Museo Del Barrio on the third Saturday of each month.)
- The FDR Four Freedoms Park is open daily 9AM to 7PM, but closed on Tuesdays. We recommend trying to get here in the early evening as the sun begins to set on the city.
Getting to the Upper East Side Trailhead
Start this route at the Central Park North subway station (lines 2 & 3).
Upper East Side Elevation Graph
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Upper East Side Reviews
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