Drinkers in the Big Apple have often prided themselves on being a quick and clever lot. The spirits of NYC, after all, have fueled some of the world’s best wits—including Dorothy Parker, George S. Kaufman, and Robert Benchley, who once quipped: “Why don’t you slip out of those wet clothes and into a dry martini” (although he may not have been the first to say it). If you count yourself among the smart imbibers of the Big Apple, you may want to keep your mind sharp by taking in a history lesson along with a beer or martini. 

1. THE WISHBONES OF WORLD WAR I

As one of New York’s oldest watering holes, McSorley’s Old Ale House at 15 East 7th Street (motto: “We have been here before you were born”) is packed with history, including claims that Abraham Lincoln, Ulysses S. Grant, Teddy Roosevelt, Woody Guthrie, Hunter S. Thompson, and E.E. Cummings all hoisted a few here. From the sawdust-covered floors to the tin ceiling, the walls are covered with memorabilia dating back to 1854, when it first opened its doors. You’ll find a wanted poster for John Wilkes Booth and a pair of handcuffs said to belong to Houdini. One of the more touching displays is a gas lamp covered in dusty turkey wishbones. As the story goes, soldiers shipping off in World War I left the wishbones there, intending to make a wish upon their return. They now serve as solemn reminder of those who did not return and wishes unfulfilled.

2. A BLOODY REMINDER OF LINCOLN’S ASSASSINATION 

Opened in 1885, Keens Steakhouse at 72 West 36th Street is known for its steaks and mutton. It also houses what is said to be the world's largest collection of long-stemmed churchwarden pipes (90,000!). Originally, men would come here to enjoy a meal and a smoke, but in 1905, the actress Lillie Langtry challenged the males-only policy and became the first woman customer. Along the way, many celebrities came to Keens to dine and smoke, keeping their personal pipes stored here. They included Mark Twain, Teddy Roosevelt, Babe Ruth, Will Rogers, Liza Minnelli, and Albert Einstein. While the downstairs is filled with the pipes, old photos, and menus from decades ago when a filet mignon dinner cost $2.25, the upstairs offers an amazing piece of history—a theater program that President Abraham Lincoln was holding in his hand the night he was shot at Ford’s Theater on April 15, 1865. According to a newspaper article that hangs next to the program, a young employee at the theater snatched the program from under Lincoln’s chair. That young man gifted the program to a theater owner, who eventually gave it to the owner of Keens. Many suspect that the stains on the program are from Lincoln’s blood. Keens also has a rare handwritten copy of the Gettysburg address hanging in its Lincoln room.

3. JUGS ALONG THE HUDSON

Built sometime in the late 1700s, the Ear Inn originally started as a two-and-a-half-story wooden beach house, constructed by James Brown, an African-American Revolutionary War veteran who was an aide to George Washington. (According to legend, James Brown was the black man pictured in this famous painting of Washington crossing the Delaware.) James Brown became a successful tobacco farmer and sold tobacco out of the first floor of the building, which at the time was just five feet from the Hudson River. Although the shoreline has been filled in over the years so the Hudson is now about a block and half west, a plaque in front of the Ear Inn marks where the original rocky shoreline met the isle of Manhattan. Because of its proximity to the river, the owners still pump water from the basement when the tide is in.

The building had several incarnations over the years, but has been a pub since 1835. Rip Hayman rented a room in the building for $100 in 1973 when he was a student at Columbia University. When the place went up for sale in 1977, he and a few friends bought it and began publishing a music magazine upstairs called The Ear. In an interview with The Villager, Hayman said, “The city landmarks commission didn’t allow new signage, so a coat of black paint covering the curved neon tubes of the “B” in the pub’s BAR sign was sufficient for EAR.” Visit the Ear Inn today, and you’ll see a collection of hand-blown whisky and wine jugs and bottles that were discovered in the basement. They date back to the 1830s. 

4. BITS OF GEORGE WASHINGTON

Before it was a food-and-drink establishment, the Fraunces Tavern at 54 Pearl Street was the mansion of wealthy merchant Stephen Delancey, who made his home here in 1719. At this location about four decades later, Samuel Fraunces opened The Sign of Queen Charlotte, where New York colonials could raise a pint. The establishment gradually morphed into the Fraunces Tavern, which became a hub where people met for entertainment and to exchange information. After the British surrender in the American Revolution, British troops left New York City on November 25, 1783. To celebrate this “Evacuation Day,” Washington and his men whooped it up at Fraunces Tavern with a grand feast of food and drink. Reportedly, 13 toasts were made. Just over a week later, Washington partied again at the tavern as he bid goodbye to his officers and New York City. The spirit of Washington lives on here, possibly helped by the fact that the bar’s museum keeps a lock of his hair, a piece of his casket, and a piece of one of his teeth. 

5. A MAXFIELD PARRISH MURAL WITH A SECRET JOKE

The wood-paneled King Cole Room in the stately St. Regis Hotel at 2 East 55th Street at Fifth Avenue reeks of elegance and expense. (Rooms at the hotel go for more than $750 a night and cocktails run about $25 each.) Still, a splurge can be worth it here to sit and gaze at the Maxfield Parrish mural of Old King Cole and his minions that serves as the backdrop for the bar. Parrish was a popular American illustrator and painter in the first half of the 20th century, known for his luminous colors and neoclassical style. As the story goes, the real estate mogul John Jacob Astor IV commissioned Parrish to make the work in 1906 for his bar in the Knickerbocker Hotel at 42nd and Broadway. Brought up a Quaker, Parrish was at first reluctant to make a painting for a bar, but a fee of $5000 (equivalent to more than $100,000 in today's dollars) convinced him.

Astor wanted to be portrayed as the king in the mural, and Parrish agreed. But Parrish and Astor reportedly did not have an easy relationship, so Parrish snuck a joke into the mural. If you look closely at the attendants, you'll see smiles and suppressed laughter. The rumor is that Parrish depicted a scene where King "Astor," with his sheepish grin, has just passed gas. When the Knickerbocker became an office building in the 1930s, the mural was moved to the St. Regis, which Astor had originally built. The bar's other big claim to fame: The Bloody Mary had its American debut here in 1934, and there are six variations on the menu. 

6. LAST OF THE LONGSHOREMAN'S BARS

Opened in 1945, Montero's Bar and Grill at 73 Atlantic Avenue in Brooklyn captures a time when New York's freight ports were bustling. The bar once catered to the longshoremen who loaded and unloaded the ships along the nearby East River. The small dive maintains a charming nautical theme with displays of handmade model ships, such as a giant 1873 Spanish warship. A number of them were donated by the seamen who frequented the place. Lifesavers, flags, a miniature steam engine, vintage photos, and newspaper clippings also adorn the walls and serve as a tribute to the sailors who once drank there. The bar was always known as a friendly port of call—original owner Pilar Montero closely followed when ships were arriving so she could have extra staff and beer at the ready. Twiggy did a photo shoot at the bar in the 1960s, and scenes for Last Exit to Brooklyn were filmed here in the late 1980s.

7. A WRITER'S WATERING HOLE

The short story writer O. Henry made Pete’s Tavern (129 East 18th Street) famous. The awning outside even says so. According to longstanding lore, O. Henry (William Sydney Porter) wrote “Gift of the Magi," one of his most famous tales, at a booth here back in the early 1900s, when the establishment was called Healy's. (The bar also most likely helped lead to his death from cirrhosis of the liver at age 47.) Portraits of the literary great still decorate the walls. The bar also served as an inspirational spot for Ludwig Bemelmans, who reportedly wrote the first draft of his children's classic Madeleine here in the 1930s. He supposedly penned the first draft on the back of a menu.

8. GIVE YOUR REGARDS AT THIS BROADWAY BAR

If you want to get a sense of history in the theater district of Manhattan, make a beeline to Sardi's at 234 West 44th Street. Slip into a dry martini and gaze at the caricatures of hundreds of celebrities who adorn the walls. Of the more than 1300 drawings on display, 700 were created by the Russian American cartoonist Alex Gard. Sardi's, which opened in 1927, is also the birthplace of the Tony Awards. Theater producer and director Brock Pemberton came up with the idea for the theater awards while having lunch here in 1946. And at the very first Tonys, proprietor Vincent Sardi received a special award.

9. IN THE FOOTSTEPS OF STARS AND GANGSTERS

A former Prohibition speakeasy, the William Barnacle Tavern (80 St. Mark's Place) specializes in absinthe. This quiet bar comes attached to a lot of history. It's part of Theatre 80 St. Marks, which started as a nightclub where talents such as Thelonious Monk, John Coltrane, and Frank Sinatra performed (Billy Crystal also worked as an usher). In the 1970s and '80s, the theater changed into a movie revival house. On the wall in the bar, there is a photo of Katharine Hepburn, taken by Spencer Tracy as they got his yacht ready for the season. Hepburn gave it to Theatre 80 owner Howard Otway.

Outside the bar, many great old movie stars left their footprints in cement in the sidewalk, including Myrna Loy, Gloria Swanson, Ruby Keeler, Joan Crawford, and Dom DeLuise. Those imbibing at the Barnacle can still step outside and compare their feet to those of the stars. The bar also brings to mind another kind of cement shoes: It once was Scheib's Place, a notorious speakeasy with ties to New York gangsters. Made of very rare and nearly extinct Cuban mahogany, the bar itself is original to the tap room of the speakeasy, where Al Capone drank with the City Council members. Lorcan Otway  (the current owner of the William Barnacle and Theatre 80) opened the Museum of the American Gangster on the floor above. The museum explores the history of organized crime and the speakeasy. 

10. SOAK IN THE OLD

For sheer ambience of a bygone time, it's hard to beat The Old Town Bar at 45 East 18th Street. Originally a German bar called Viemeisters when it opened in 1892, the Old Town features a 55-foot long 19th-century bar, high tin ceilings, original mirrors, gas lamps (now electrified), and antique cash registers. The men's room is renowned for its gigantic urinals built by Hinsdale in 1910. In 2010, the bar hosted a 100-year anniversary champagne party to celebrate its majestic latrines. This establishment also holds a record for having the oldest New York dumbwaiter, which still delivers food from the upstairs kitchen down to the bar.