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As someone with multiple higher education degrees, I can confidently say that the New York City Sightseeing Guide Exam was the most difficult test I’ve ever taken. But if you want to give public ticketed tours within the five boroughs—even if, in my case, you’re merely leading historically-inspired pub crawls around Brooklyn—you have to pass the exact same monstrous Department of Consumer Affairs exam as every other tour guide in the city covering a broad swath of NYC history, geography, mass transit, ecology, and other minutiae. Everyone’s in the same boat, from the barkers aboard double-decker buses to spandex-clad cyclists guiding hoards of tourists through Central Park, and it’s an incredibly dense and detailed boat at that.
To prepare, I forced myself to only consume media that had something to do with New York City. Every book I read, podcast I listened to, and movie or TV show I watched closely orbited my hometown for the six weeks leading up to my test date. I ended up passing, but while my internal treasure trove of obscure New York factoids rarely came up on my craft beer-fueled pub crawls, I did begin to look at the city in a new light. When people visited from out of town, I made a point of veering away from the standard Times Square, High Line, and Central Park rigamarole in favor of equally impressive but lesser-known destinations that stand out from the crowd.
The next time you find yourself wandering the streets of Manhattan, leave the beaten track behind and check out these 10 off-the-beaten-path NYC destinations.
Filmmakers Alex Kalman, Josh Safdie, and Benny Safdie are behind this elevator shaft turned modern natural history museum and adjacent gift shop, tucked away down a nondescript Tribeca alley. The 36-square-foot space’s shelves display an ever-surprising collection of commercial oddities and historical artifacts and visitors can call an 800 number to access an in-depth audio guide detailing the significance of each curious item. Described as “object journalism,” the exhibits often have political or cultural undertones and recent highlights include the shoe thrown at George W. Bush at the Minister’s Palace in Baghdad, a pair of dice fashioned by an inmate at a US prison, a bottle of knockoff “Hoed & Shouders” shampoo from Venezuela, and a takeout box from Iran’s faux-McDonalds, McMashallah.
Mmuseumm is open to the public (three at a time) on Fridays, Saturdays, and Sundays from 11 a.m. to 6 p.m. and asks for a $4 suggested donation. But if it’s closed, don’t worry—you can view the entire collection via peepholes in the security grate. 4 Cortlandt Alley
Just outside famously quirky developer Melvyn Kaufman’s Financial District high rise sits this dark clapboard penny candy store with an eye-catching yellow and red striped awning, sticking out like a sore thumb among the area’s many cell phone stores and office buildings. And while it might look like a throwback from yesteryear, it’s actually a modern convenience store built to resemble a turn-of-the-century soda fountain with an antique cash register, a vintage stained glass Coca Cola ceiling lamp, and a broad u-shaped counter dotted with glass candy jars. But that’s not 77 Water Street’s only surprise—Kaufman also installed a World War I replica fighter jet on the building’s roof, complete with an Astroturf runway, landing lights, and a windsock. 77 Water Street
The next time you make the trip up to Yankee stadium, skip the subway and opt for this scenic footbridge stretching from Washington Heights across the Harlem River to the Bronx. The oldest standing bridge in New York, it began life in 1848 as a part of the Croton Aqueduct system, and opened up its walkway for public crossings in 1864. In the following decades, however, the 140-foot-tall and 1450-foot-long expanse fell into disrepair and was eventually closed in the 1970s. In 2012, local groups began petitioning the city to bring the landmark bridge back up to code and the walkway officially reopened in 2015. Today, Manhattan offers no better place to take in breathtaking panoramic views on a breezy summer afternoon. West 172nd Street & Amsterdam Avenue
Blink and you might miss this eccentric West Village landmark. Embedded in the sidewalk in front of the iconic Village Cigars, the 500-square-inch tile triangle commemorates real estate holdout David Hess, a West Village building owner who fought tooth and nail against eminent domain demolition orders from 1910 to 1914, at which point the city had usurped all but a small section of the building’s foundation. When the city finally asked Hess to hand over the last of his property, he adamantly refused, instead, decorating the piece of concrete with mosaic tiles reading “Property of the Hess Estate Which Has Never Been Dedicated For Public Purposes.” In 1938, Village Cigars purchased the triangle for $1000, vowing to maintain it as a tribute to Hess’ defiant perseverance. 110 7th Avenue
30 fiberglass fish spin, swarm, and glide through the air on individual motors at this unique 2015 Battery Conservancy project designed by famed Broadway artist George Tsypin. The illuminated sea creatures represent 12 different real fish species, from angelfish to clownfish, and each are equipped with internal speakers broadcasting a soundtrack inspired by ocean sounds as well as a seat for their human riders. The inventive carousel is an homage to nearby landmark building Castle Clinton, the site of the original New York Aquarium, which welcomed millions of museum-goers as one of the country’s first public aquariums from 1896 until its closure in 1941. Battery Park
Many bars claim to be New York’s oldest, but evidence suggests this Spring Street dive, in continuous operation since 1817, might actually hold the title. The modest Federal-style brick building was constructed in the late 18th century on what was then the bustling banks of the Hudson River. It housed James Brown, an African-American Revolutionary War vet who served heroically as George Washington’s aide, along with Brown’s ground floor tobacco business. Records show that a tavern existed in some form on the property as early as the 1830s, but historians suspect visiting sailors and local businessmen were frequenting the place for drinks even before then. In 1890 it was sold to an Irish brewer named Thomas Cloke, who installed a brewery in the bar’s back room and kept longshoremen in good spirits upfront before selling his business in 1919 in anticipation of Prohibition’s wrath. The bar survived Prohibition thanks to a series of owners who converted the upstairs apartment into a boarding house and brothel while illicitly selling booze downstairs. Afterward, the tavern lost its name and gained a seedy reputation as the go-to spot for hard-drinking seamen. Then, in the 1970s, a group of young artists who published a music magazine called The Ear out of the bar’s top floor cleaned up the landmark tavern and reopened it to the public, painting over the hanging neon BAR sign’s B so it read EAR. These days you can find many of the original details inside the bar, from an old-school phone booth to antique signs and hand-carved furnishings, along with a stellar burger, plenty of cold beer, and perhaps even a ghost or two. 326 Spring Street
At over 131 feet tall with a trunk diameter of 67 inches, passersby can’t help but notice the stately English Elm situated on the park’s northwest corner. But few of them know that the shade they’re enjoying is actually provided by Manhattan’s oldest living tree. The mighty tree was dubbed “the Hangman’s Elm” or “the Hanging Tree” sometime in the 19th century due to its rumored history as a site for executing traitors during the American Revolution. Official sources have determined the tree to be at least 300 years old, though other records suggest it’s 30 to 40 years older than that. Washington Square Park
Roam the lush grounds of this Upper West Side destination and you might catch a glimpse of three very beautiful New Yorkers: Harry, Jim, and Phil, a trio of peacocks that have called the Amsterdam Avenue sanctuary home since the early 2000s (they’re such headturners, one even has a Twitter account). After watching the birds strut their stuff or duck into their custom-built hutch for a nap, hop on a vertical tour of the magnificent Gothic Revival building, which broke ground in 1892 and stands as the world’s largest Anglican cathedral. The guided tour takes visitors up 124 feet of spiral staircases past stained glass windows and important period art to the open-air roof for a stunningly scenic finish. 1047 Amsterdam Avenue
When New York’s oldest Dim Sum restaurant opened its doors in 1920, Doyers Street was a very different place than the sleepy restaurant-lined nook it is today. The narrow Chinatown bend was rife with gambling, human smuggling, kidnapping, secret underground tunnels, and warring street gangs, earning it the nickname the Bloody Angle. These days you won’t find any hatchetmen lurking in the shadows but you will find this quaint family-run eatery perched on the crooked street’s southwest corner. The vintage cafeteria-style institution acts as a welcome blast-from-the-past, serving the same delicious pork dumplings, steamed buns, and other Chinese delights that first put it on the City’s culinary map out of its iconic wood-paneled storefront. 3 Doyers Street
The martinis are undoubtedly some of the city’s best, but that’s not the only reason New Yorkers love this Upper East Side hideaway inside The Carlyle Hotel, an American Express Fine Hotels & Resorts property. The real draw is the pale yellow walls, famously blanketed in Madeline creator Ludwig Bemelmans’ playful hand-painted illustrations. Visitors to the Art Deco lobby bar sip cocktails delivered by tuxedoed servers against a backdrop of live piano and Bemelmans’ whimsical interpretation of Central Park, depicting animals large and small happily exploring the terrain alongside picnicking families. Legend has it that Bemelmans wasn’t paid for his work but instead was allowed to live at the luxurious hotel for free with his family while he worked on his mural. To this day, these walls remain the world’s only example of Bemelmans’ art open for public viewing. 35 East 76th Street