CitySketch New York City by Melissa Wood: Nearly 100 Creative Drawing Prompts for Sketching the Big Apple

HOW TO USE THIS BOOK Big cities are full of promise. From the amazing art and architecture to the diverse food and culture, each city has its own unique collection of treasures to unearth. CitySketch is the perfect way to sketch the delights of your favorite urban retreat. Each page contains a fascinating anecdote as well as a creative prompt about a unique and lovable part of the city. On the opposite side of the page, a sketch is started for you. Then it’s up to you to unleash your imagination to complete the sketch and add your own signature style to it. You can use CitySketch to practice sketching and doodling, to enhance your creativity, or simply to capture your favorite city on paper. So get out your pencil and start dreaming!

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ARCHITECTURE

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Flatiron Building (1902) It may seem unlikely that an iconic architectural marvel should be nicknamed for a small household appliance, but that was the fate of the triangular-shaped Flatiron Building, located at Fifth Avenue and 23rd Street. Cleverly designed to fit within an elongated, iron-shaped plot of land by the great Chicago architect Daniel Burnham, the building was a wonder of Renaissance, beaux-arts, and modern ingenuity.

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Sketch a group of rocking revelers dashing past the base of the Flatiron on their way to a concert at Madison Square Garden.

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Flatiron Building (1902) It may seem unlikely that an iconic architectural marvel should be nicknamed for a small household appliance, but that was the fate of the triangular-shaped Flatiron Building, located at Fifth Avenue and 23rd Street. Cleverly designed to fit within an elongated, iron-shaped plot of land by the great Chicago architect Daniel Burnham, the building was a wonder of Renaissance, beaux-arts, and modern ingenuity.

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Sketch a group of rocking revelers dashing past the base of the Flatiron on their way to a concert at Madison Square Garden.

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The Empire State Building (1930) Hop aboard the elevator to the top of the Empire State Building, and you’ll be in good company. Cary Grant, Deborah Kerr, Meg Ryan, and Tom Hanks are just a handful of the actors who’ve lured us up to the top to take in the view, thanks to countless movie scenes set on the building’s observation deck. Built in 1930 during the Great Depression, this skyscraper, once the world’s tallest, became a beacon to the world that boasted of New York’s prominence.

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Sketch Manhattan from the observation deck of the Empire State Building, looking south toward the Statue of Liberty.

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The Empire State Building (1930) Hop aboard the elevator to the top of the Empire State Building, and you’ll be in good company. Cary Grant, Deborah Kerr, Meg Ryan, and Tom Hanks are just a handful of the actors who’ve lured us up to the top to take in the view, thanks to countless movie scenes set on the building’s observation deck. Built in 1930 during the Great Depression, this skyscraper, once the world’s tallest, became a beacon to the world that boasted of New York’s prominence.

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Sketch Manhattan from the observation deck of the Empire State Building, looking south toward the Statue of Liberty.

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The Metropolitan Museum of Art From classic American paintings and Roman sculptures to intricate Islamic pieces, the Met holds over two million works of art.

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Draw the human head with the folded head cloth of the Sphinx of Hatshepsut (c. 1473–1458 B.C.) as it extends into the body of a lion. This seven-ton granite sculpture portrays the powerful female pharaoh Hatshepsut and is one of a number of sphinxes at the Met.

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The Metropolitan Museum of Art From classic American paintings and Roman sculptures to intricate Islamic pieces, the Met holds over two million works of art.

C

Draw the human head with the folded head cloth of the Sphinx of Hatshepsut (c. 1473–1458 B.C.) as it extends into the body of a lion. This seven-ton granite sculpture portrays the powerful female pharaoh Hatshepsut and is one of a number of sphinxes at the Met.

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New York City Ballet Famed choreographer George Balanchine was one of the ballet’s founding members back in 1948. Today, as many as 60 performances a year are held at Lincoln Center, where they are enjoyed by aficionados from all over the world. Made up of 90 dancers, the company usually sells out every performance, particularly when a classic like Swan Lake is being performed.

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Sketch the white swan Odette, the Queen of the Swans, dancing with her prince. Like a Degas painting, also draw all her swans in the background forming two parallel lines and wearing beautiful tutus and headpieces. In the corner of the page, draw a pair or two of well-worn ballet slippers.

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New York City Ballet Famed choreographer George Balanchine was one of the ballet’s founding members back in 1948. Today, as many as 60 performances a year are held at Lincoln Center, where they are enjoyed by aficionados from all over the world. Made up of 90 dancers, the company usually sells out every performance, particularly when a classic like Swan Lake is being performed.

C

Sketch the white swan Odette, the Queen of the Swans, dancing with her prince. Like a Degas painting, also draw all her swans in the background forming two parallel lines and wearing beautiful tutus and headpieces. In the corner of the page, draw a pair or two of well-worn ballet slippers.

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Broadway Broadway is the oldest north-south thoroughfare in New York City. Running all the way from the southern tip of the island to the Bronx, most of the action falls between 42nd and 47th streets, where big, high-end theatrical and musical productions run the show. If you can make it here, you can make it anywhere!

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Add to the busy street scene at 42nd and Broadway. Include the vertical Broadway sign framed in bright lights. Add marquees featuring all the shows that are running, billboards, and your own name in large print as the lead in your favorite musical!

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Broadway Broadway is the oldest north-south thoroughfare in New York City. Running all the way from the southern tip of the island to the Bronx, most of the action falls between 42nd and 47th streets, where big, high-end theatrical and musical productions run the show. If you can make it here, you can make it anywhere!

C

Add to the busy street scene at 42nd and Broadway. Include the vertical Broadway sign framed in bright lights. Add marquees featuring all the shows that are running, billboards, and your own name in large print as the lead in your favorite musical!

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Major League Baseball For New Yorkers, baseball isn’t really a sport or cultural event: it’s a religion. With two major league teams in town, the Mets and the Yankees, every family has an allegiance to one or the other. While it’s acceptable to groan about your team’s performance, it would be sacrilegious to ever change sides. Ever.

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Imagine an aerial view of Yankee Stadium. Show the pristine diamond, the bleachers, the Yankees logo behind home plate as well as the billboards and ads above the seats. Or sketch the open airstadium including some of the high-rises and office buildings of the Bronx in the background.

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Major League Baseball For New Yorkers, baseball isn’t really a sport or cultural event: it’s a religion. With two major league teams in town, the Mets and the Yankees, every family has an allegiance to one or the other. While it’s acceptable to groan about your team’s performance, it would be sacrilegious to ever change sides. Ever.

C

Imagine an aerial view of Yankee Stadium. Show the pristine diamond, the bleachers, the Yankees logo behind home plate as well as the billboards and ads above the seats. Or sketch the open airstadium including some of the high-rises and office buildings of the Bronx in the background.

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New York Fashion Week Statuesque models, frosty editors, A-list celebrities, fashion bloggers, and photographers congregate for the semiannual fashion extravaganza known as New York Fashion Week. With hyper-exclusive designer shows, legendary parties, and plenty of air kisses, it’s a whirlwind of a week to celebrate the sartorial happenings of tomorrow.

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Clear your diaries because you’ve managed a hot ticket to one of Fashion Week’s most exclusive parties, and it’s your opportunity to brush shoulders with anyone who is anyone. Beautiful people mingling and free-flowing champagne set the scene; now it’s up to you to fill in the gaps and set the tone.

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New York Fashion Week Statuesque models, frosty editors, A-list celebrities, fashion bloggers, and photographers congregate for the semiannual fashion extravaganza known as New York Fashion Week. With hyper-exclusive designer shows, legendary parties, and plenty of air kisses, it’s a whirlwind of a week to celebrate the sartorial happenings of tomorrow.

C

Clear your diaries because you’ve managed a hot ticket to one of Fashion Week’s most exclusive parties, and it’s your opportunity to brush shoulders with anyone who is anyone. Beautiful people mingling and free-flowing champagne set the scene; now it’s up to you to fill in the gaps and set the tone.

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Pizza

Dim Sum in Chinatown

Staunch purists flock to Totonno’s, adventurous foodies hit Paulie Gee’s, and locavores love Arturo’s . . . When it comes to pizza, New Yorkers have an embarrassment of riches. The perfect pizza pie hits all the right notes of saltiness, tang, and chew.

Dim sum is a group affair: The more people at the table, the more to sample. The menus offer an array of exotic flavors and textures: plump shrimp and scallop dumplings, savory pan-fried noodles, salty deep-fried squid, glazed eggplant stuffed with minced shrimp, shiny custardy egg tarts, mounds of garlicsautéed pea shoots, and sweet black sesame rice balls.

C

The perfect thin-crusted pie comes fresh out of a coal-burning oven, and it’s up to you to create the right balance of toppings. What tickles your fancy: a pared-down Margherita, a white clam pie, or maybe something a bit more daring?

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C

The bamboo steamers and plates are on the table; now you just need to create an arrangement of bite-sized morsels. Be sure to include a dish of noodles or gai lan with oyster sauce.

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Pizza

Dim Sum in Chinatown

Staunch purists flock to Totonno’s, adventurous foodies hit Paulie Gee’s, and locavores love Arturo’s . . . When it comes to pizza, New Yorkers have an embarrassment of riches. The perfect pizza pie hits all the right notes of saltiness, tang, and chew.

Dim sum is a group affair: The more people at the table, the more to sample. The menus offer an array of exotic flavors and textures: plump shrimp and scallop dumplings, savory pan-fried noodles, salty deep-fried squid, glazed eggplant stuffed with minced shrimp, shiny custardy egg tarts, mounds of garlicsautéed pea shoots, and sweet black sesame rice balls.

C

The perfect thin-crusted pie comes fresh out of a coal-burning oven, and it’s up to you to create the right balance of toppings. What tickles your fancy: a pared-down Margherita, a white clam pie, or maybe something a bit more daring?

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C

The bamboo steamers and plates are on the table; now you just need to create an arrangement of bite-sized morsels. Be sure to include a dish of noodles or gai lan with oyster sauce.

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The Cocktail

Tacos

Whether you favor an old-fashioned at a cozy haunt or a sleek martini at an ultra-modern hotel, cocktails in the world’s happy hour capital are otherworldly. Top-notch mixologists combine premium spirits with original infusions and unusual ingredients to create some of the finest concoctions for the urban sybarite. Just be sure to leave your inhibitions at the door.

Tacos are enjoying a renaissance: Taquerías have opened up throughout the five boroughs, taco trucks are cropping up after dark, and foodies are flocking to some of city’s finest. Who could blame them? Slow-cooked beef or pork stewed with aromatics and seasonings, nestled on corn tortillas, and topped with fresh cilantro, onion, and guacamole, and cheese . . .

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In a dim-lit downtown speakeasy evocative of the Roaring ’20s, the head bartender serves a row of his finest tipples. Complete the sketch with the classic drinks and craft beer for an authentic taste of the past.

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You’ve been served! With a freshly prepared taco on hand, add your favorite fixings: diced tomato, sliced radishes, chopped onions? Possibly some cilantro? Generous servings of salsa verde?

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The High Line A mile-long public greenway on an elevated former railway line, the High Line opened in 2009 along the lower West Side of Manhattan. Running from the Meatpacking District to West 34th Street, the High Line was inspired by Promenade Plantée, a similar elevated walkway in Paris that includes cafés and bars along the lovingly landscaped path.

C

Fill out this aerial view of the High Line’s wooden walkway. Add the green grass, plants, and flowers nestled among the skyscrapers on either side.

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The High Line A mile-long public greenway on an elevated former railway line, the High Line opened in 2009 along the lower West Side of Manhattan. Running from the Meatpacking District to West 34th Street, the High Line was inspired by Promenade Plantée, a similar elevated walkway in Paris that includes cafés and bars along the lovingly landscaped path.

C

Fill out this aerial view of the High Line’s wooden walkway. Add the green grass, plants, and flowers nestled among the skyscrapers on either side.

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Coney Island With its three miles of sandy beaches, boardwalks, and amusements, it’s easy to see why New Yorkers find Coney Island an ideal retreat from the hot and humid summer in the city.

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Draw the crowds on the boardwalk eating hot dogs and waiting for the famous Parachute Drop. Add the Ferris wheel, food stands, and high-rise buildings in the background.

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Coney Island With its three miles of sandy beaches, boardwalks, and amusements, it’s easy to see why New Yorkers find Coney Island an ideal retreat from the hot and humid summer in the city.

C

Draw the crowds on the boardwalk eating hot dogs and waiting for the famous Parachute Drop. Add the Ferris wheel, food stands, and high-rise buildings in the background.

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The Brooklyn Bridge The massive suspension bridge across the East River that connects Brooklyn and Manhattan is a marvel of engineering beauty, and most people don’t realize there is even a path for pedestrians and cyclists to use for crossing.

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Finish sketching a view across the bridge from either the Manhattan or Brooklyn end of the pedestrian walkway. Include one of the Gothic-style stone arches along with the spiderweb-like steel cables in the foreground.

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The Brooklyn Bridge The massive suspension bridge across the East River that connects Brooklyn and Manhattan is a marvel of engineering beauty, and most people don’t realize there is even a path for pedestrians and cyclists to use for crossing.

C

Finish sketching a view across the bridge from either the Manhattan or Brooklyn end of the pedestrian walkway. Include one of the Gothic-style stone arches along with the spiderweb-like steel cables in the foreground.

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Brooklyn Hipsters In the 1950s and ’60s, New York had its hepcats and hippies. Today, a hipster in Brooklyn is as easy to spot as a yellow taxicab in Manhattan. Cross the Williamsburg Bridge from the Lower East Side into Brooklyn, and you are officially in the hipster capital of the country—possibly even the world. It’s all about the ’Burg, bro.

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Hipsters travel in small packs, and their natural habitat, like their 1960s counterparts, is in an urban village-like setting. Be sure to sketch several twentysomethings holding a local Brooklyn brew in one hand and a hand-rolled cigarette in the other. 1970s slogan T-shirts, ironic trucker caps or fedoras, thick plastic eyeglasses, as well as beards on the guys and cropped hair on the girls complete the look.

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Brooklyn Hipsters In the 1950s and ’60s, New York had its hepcats and hippies. Today, a hipster in Brooklyn is as easy to spot as a yellow taxicab in Manhattan. Cross the Williamsburg Bridge from the Lower East Side into Brooklyn, and you are officially in the hipster capital of the country—possibly even the world. It’s all about the ’Burg, bro.

C

Hipsters travel in small packs, and their natural habitat, like their 1960s counterparts, is in an urban village-like setting. Be sure to sketch several twentysomethings holding a local Brooklyn brew in one hand and a hand-rolled cigarette in the other. 1970s slogan T-shirts, ironic trucker caps or fedoras, thick plastic eyeglasses, as well as beards on the guys and cropped hair on the girls complete the look.

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ABOUT THE AUTHORS MELISSA WOOD is both an illustrator and writer. Her permanent case of wanderlust, coupled with her addiction to history and lifelong love of travel is how the Citysketch series was born. She lives and works in the country, a stone’s throw from the energy of Chicago. She has three witty children, two poorly behaved dogs, and one fluffy cat.

MICHELLE LO studied at the Fashion Institute of Technology and The New School University. After working as an editor, she obtained a chef-training degree and has since worked on numerous cookery books, by leading chefs such as René Redzepi and Ferran Adrià. Michelle is currently a freelance writer and editor and devotes her life to the pursuit of food and style with her photographer husband and young daughter. MONICA MEEHAN is a freelance writer and author of The Viennese Kitchen: Tante Hertha’s Book of Family Recipes. She also works in publishing and divides her time between New York and London. Monica is an avid traveler, cook, and people-watcher. JOANNE SHURVELL is an award-winning travel and arts writer. She is also the owner of PayneShurvell, a contemporary art gallery in London.

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