Walking Tour of Greenwich Village

By Terry Sisk

My 45-minute self-guided walking tour starts from the corner of West Eighth and Macdougal Streets and continues south down the full six block length of Macdougal Street, the heart of Greenwich Village, with a few deviations to take in Washington Square and two private alleys.

Make your way to W. 8th St. & Macdougal 
by subway from either:
8th  St./Broadway station (lines N, R, Q, W)
W. 4th St./Washington Sq. station (lines A, C, E, F, V)
Christopher St/Sheridan Sq. station (lines 1, 2, 3, 9)

Click map to enlarge

Both a street and an alley were named after Alexander McDougall (1731-1786), a Major General of the American Revolutionary War. Born in Scotland, he became an American  merchant seaman, an importer, founding President of the Bank of New York, delegate to the Continental Congress and a New York State senator. He also spelled his last name with “Mc” instead of “Mac” and with two “L’s,” so it is a mystery why the streets that honor him use a spelling variant. Although he prospered, McDougall was never accepted into New York’s high society; he spoke with a crude Scottish accent, was loud and unpolished and wore gaudy clothes. It didn’t help that he liked to remind the locals that upon his family’s arrival in New York, he first worked as a milk delivery boy for a dairy. Not to mention that he was jailed in 1770 for writing an anti-British pamphlet.

Macdougal Street

This historic street (one-way going south) skirts the western perimeter of Washington Square Park and runs north to south for six blocks from Eighth to Prince Street. Considered the heart of Greenwich Village, the street is so dense with historic significance that a walk along its sidewalks almost overwhelms the senses. Nearly every location on this walking tour is on Macdougal, or just a few steps off it. The following sites deserve our notice. Listed north to south, all are on the west side of the street (on the right going south) unless noted:

■ 32 West Eighth Street, at the SE corner of Macdougal, is the former location of 8th Street Books, the bookseller where Bob Dylan and Allen Ginsberg first met in 1964.

■ 179 Macdougal was formerly the Bon Soir cabaret, where Barbra Streisand and Woody Allen performed as unknowns.
   

■ 171 Macdougal. The controversial, severe brick façade of the 10th Church of Christ Scientist lasted only 40 years before it was stripped away in 2007, revealing the original street front of an 1890s factory building (at right). In 1966 modernist architect Victor Christ-Janer had provided the church with a stark orange brick resurfacing design (photo below), which left the original facing intact. This was one of the most striking ecclesiastical building façades in the history of New York – now lost to historic preservation. The church decided to sell the unused upper floors in 2006, which have been converted to condominium residences. The church used part of the funds to redesign its ground floor chapel and offices into more distinctive spaces.

■ Macdougal Alley. Just across the street is the iron gate marking the entrance to an 1830s-era  private mews that was home to the stables and gardens servicing patrician houses in the area. Heiress Gertrude Vanderbilt Whitney lived at number 19, among her artist friends, supporting them by buying their creations; her personal collection was the nucleus of the Whitney Museum of American Art, originally located here at numbers 15 ½ and 17 ½, later incorporating number 19, and since relocated farther uptown.

Artist Jackson Pollock lived at number 9 from 1949 through 1950. Standing before number 15 is one of the few remaining original NYC gaslights. In fact, this was the last NYC street to remain lit by gaslight; they were not replaced by electric ones until the late 1930s. This is another block of residences nowadays occupied mostly by New York University professors, although a few are private – one sold two years ago for $5.5 million, boasting private street parking, two working fireplaces and double height ceilings. This alley was turned into a cul-de-sac in the 1950s when a large apartment building was constructed at the east end of the lane, blocking its access to Fifth Avenue. Until that time Washington Mews and Macdougal Alley formed a straight line from University Place west across Fifth Avenue to Macdougal Street.

■ 101-103 Waverly Place is the address for the main entry to the Washington Square Hotel, but the last awning on Macdougal before turning right onto Waverly announces the North Square Restaurant, where Norah Jones got her start as a waitress who was allowed to sing during Sunday brunches.

Shortly after it opened in 1902 as the residential Hotel Earle (named after its first owner), a second identical building was constructed, the two connected to form one larger hotel. Ernest Hemingway stayed at this hotel for several weeks, just before departing for Europe for WW I in 1914. In 1917 Earle L’Amoureux purchased the adjacent brick building, bringing his hotel all the way to the corner of Macdougal. Dylan Thomas stayed here in 1950 after being evicted from the Beekman for rowdy behavior; Bob Dylan stayed here in 1961 when he arrived from Minneapolis at the tender age of 20. Other guests have included Joan Baez, Bo Diddley, Bill Cosby, Barbra Streisand, Patricia Highsmith and the B-52s. The hotel is today a pleasant, affordable tourist hotel at a great location, with snug rooms and a handsome Art Deco bar. Retrace your steps back to Macdougal.

■ 27-28 Washington Square North, at the NE corner of Macdougal, is the former residence of Matthew Broderick and Uta Hagen. Called the Richmond Hill Apartments, the building is named after the 1770s era Greenwich Village estate of Major Abraham Mortier, later occupied by General George Washington as a headquarters and subsequently owned by Aaron Burr, third Vice President and killer of Alexander Hamilton.

Note: Cross over Macdougal, noticing that as you walk to the east the street is named Washington Square North for two blocks. West and east of Washington Square Park the street is named Waverly Place, after Sir Walter Scott’s historical novel Waverley (note spelling difference), to honor him on the year after his death in 1832.

■ Washington Square North: This series of 19th-century row houses was built as an income generating project for Sailor's Snug Harbor, the nation’s first home for retired merchant seamen. Established in 1801 by the will of Captain Robert Randall, the charity housed 900 “aged, decrepit and worn-out” seamen on a 130 acre waterfront complex on Staten Island. By the late 19th century Sailors' Snug Harbor was among the wealthiest charities in New York, with its Washington Square and Eighth Avenue residences yielding rich rents at a surplus of $100,000 a year. These Greenwich Village properties were built on land that had been Randall’s farm. The construction of this row of houses in 1831 was also the city’s first delineation of distinct residential and commercial districts; the strict absence of trade and industry was stipulated in the land lease. The Row was originally home to some of New York City's foremost merchants, bankers, community leaders and cultural figures. Among the original lessees were New York University council members (numbers 5 and 7); number 3 was where John Dos Passos wrote Manhattan Transfer, and where artists Edward Hopper and Rockwell Kent painted; number 18 (demolished in 1952 for No. 2 Fifth Ave. apartments) was the home of Henry James’s grandmother, and the time he spent there as a boy was reflected in his 1880 novel, Washington Square. Later Row residents included architect Richard Morris Hunt and founding president of the Metropolitan Museum of Art John Taylor Johnston. Number 1, since demolished, was once the home of Edith Wharton. Stylistic unity, high quality construction, extra wide and deep lots, interior luxury features and facades set back twelve feet from the street’s property line made this block of houses among the most lavish of its time. Washington Square North is today one of the finest rows of Greek Revival houses in the country.

■ Washington Square Park, on the right side of the street, runs between Macdougal and University Place. It is the southern terminus of storied Fifth Avenue, which forms the delineation of East and West street addresses in Manhattan. Originally a marsh surrounding Minetta Brook, which ran from 23rd Street all the way to the Hudson River, the park’s acreage was once used as a graveyard for slaves and yellow fever victims, a dueling ground and a place of execution during the city’s early days. After a brief stint as a military parade ground, the tract was made a park in 1850.

The Memorial Arch was originally a temporary wooden monument built in 1899 for the centennial of George Washington’s inauguration. It proved so popular that funds were raised to replicate it in stone. The sculpture of Washington on the west pier is by Alexander Stirling Calder, the father of artist Alexander Calder (1898-1976), noted for his 20th-century mobiles.

■ Cross over Fifth Avenue and turn left, continuing north on Fifth for a half block; turn right into Washington Mews (photo below), a private gated lane that runs through to University Place. Like Macdougal Alley, it was the location of former stables and gardens of the area’s grander houses. John Dos Passos, author of USA, once lived at number 20a, and sculptor Paul Manship, creator of the gilded Prometheus statue overlooking the ice-skating rink at Rockefeller Center, resided at number 44. Donald Desky designed the interiors of Radio City Music Hall while working at number 46. Edward Hopper died here in 1966. Gertrude Vanderbilt Whitney, aunt of Gloria Vanderbilt and great-aunt of Anderson Cooper, lived at number 60 for the last two years of her life; at the time Washington Mews was near the former home of the Whitney Museum.

The original 1881 iron gate at University Place was replaced by an elaborate Mediterranean style brick and stucco gateway with lanterns in 1916, when the automobile displaced horses and carriages; unfortunately the gateway has since been rebuilt in plain red brick. About this time Sailor’s Snug Harbor, private owners of the mews, converted 12 of the two-story brick stables to artist studios, facing the brick with stucco and decorative tiles. The stables lined the north side of the mews; the structures on the south side were built later, during the 1930s. In 1950 New York University leased the residences along Washington Mews as faculty housing and offices. The mews even today retains its distinctive Belgian block pavement, now worn down sufficiently to resemble cobblestones. Still private property, NYU built a six-foot-high gate at the Fifth Avenue entry in the late 1980s, locked at night to protect residents, although pedestrians during daylight hours are not strictly discouraged.

■ 1 University Place. Walk the full length of the mews and turn right onto University Place. On the northeast corner of Washington Square Park, where Waverly Place and University Place intersect, catercorner from the park, stands No. 1 University Pl., a former home of playwright Clifford Odets. Cross over to the left side of University Place and continue walking south, so that the park is situated across the street on your right. All of the buildings on your left now belong to New York University.

■ New York University. Washington Square is home to one of five campus centers of New York University, the city’s largest private school of higher learning. NYU was established in 1831 by a group of prominent New Yorkers, led by Albert Gallatin, who was Secretary of the Treasury under Thomas Jefferson. Unlike other institutions at the time, it was nonsectarian and meant to produce a different sort of elite citizen, not born to privilege, but set apart for leadership by talent and effort. To that end it provided a more practical education, what the 19th century called "Useful Knowledge." The heart of NYU is its Washington Square campus, where more than 15,000 students enjoy the unique atmosphere of Greenwich Village.

■ 23-29 Washington Place. Make the first left onto Washington Place. At the end of the block on your left, at the near corner of Greene Street stands a 1901 vintage 10-story NYU science building, formerly the scene of the gruesome Triangle Shirtwaist Factory fire of March 25, 1911, in which 146 garment workers laboring on the top three floors perished behind locked exit doors. After the exterior fire escapes collapsed, many of those trapped inside were burned alive or jumped to their deaths onto the sidewalks below. The tragedy led to wide-ranging legislation requiring improved factory safety standards and helped spur the growth of the International Ladies' Garment Workers' Union. Three plaques on the SE corner of the refurbished building commemorate the men and women who perished.


Retrace your steps to the NE corner of Washington Square Park and stroll along the park's northern perimeter to make your way back to Macdougal Street.

■ 29 Washington Square West

At the SW corner of Waverly Place & Macdougal, this is where Eleanor Roosevelt took an apartment in 1942; it became her main residence from President Franklin D. Roosevelt's death in 1945 until 1949, during which time she played a large role in the workings of the United Nations.

■ The southwest corner of Washington Square Park (which flanks the east side of Macdougal Street) is the site of many historic chess games; the movie Searching for Bobby Fischer was filmed here.

■ 38 Washington Sq. South (SE corner of Macdougal and Fourth Street) is where Eugene O'Neill lived in a boarding house in 1916, when he was having an affair with Louise Bryant (Mrs. John Reed). The earlier building was replaced by the NYU School of Law’s Vanderbilt Hall in 1951.

■ 137 Macdougal Street (upstairs) was the home base of the Liberal Club during 1913-1919. Members included Sherwood Anderson, Theodore Dreiser, Max Eastman, Emma Goldman, Sinclair Lewis, Jack London, Margaret Sanger, Upton Sinclair, and Lincoln Steffens. The Heterodoxy Club, a radical feminist organization that counted 11 of the adjacent Provincetown Players as members, also met here in a street level restaurant run by Evanston-born anarchist Paula Holladay. In the 19th century this was the staid address of Nathaniel Currier, one of the partners of the artist team Currier and Ives.

■ 133 Macdougal is home to the Provincetown Playhouse, where the plays of Eugene O’Neill were first staged. In 1918 four buildings were converted from a bottling plant and stables into a theater for the Provincetown Players, whose members included O’Neill, Edna St. Vincent Millay and Djuna Barnes. Paul Robeson and Tallulah Bankhead performed here, e. e. cummings had his plays staged here, and Bette Davis made her New York stage debut on these premises. The building barely escaped the wrecking ball in 2008 when NYU announced plans to raze it. Instead, they spent $4.5 million over two years to restore it, adding 30 apartments for NYU law students.

■ 146 Macdougal, across the street, replaces a building that once housed a Caribbean restaurant where James Baldwin worked as a waiter. Regular patrons included Paul Robeson, Marlon Brando, Eartha Kitt, and Henry Miller.

■ 144 MacDougal, also on the East side of the street, is a NYU law school building that replaced a former print shop used by Anais Nin, who borrowed $175 to self-published her first three books here.

■ 129 Macdougal is an 1820s Federal style building that was home to Eve's Hangout (1925-26), a tearoom and speakeasy run by Eve Addams, the pseudonym of a Jewish Polish émigré known as “Queen of the Third Sex”; her sign stated “Men Admitted But Not Welcome”. Police raided the business, and Addams was convicted of obscenity and subsequently deported for writing a story collection called Lesbian Love.

Numbers 125, 127 (Tea Spot) and 129 Macdougal (La Lanterna di Vittorio) were three lots once owned by a downtown hat merchant, on land that was originally part of the Elbert Herring farm. Number 129, which also houses The Bar Next Door, a basement jazz room, features pineapple newel posts on the entry ironwork, one of the few such remaining pairs in Greenwich Village. Iron pineapples on railings were a symbol of hospitality; traditionally a returning seaman would set one on his stoop to show that he was home and receiving visitors. 129 Macdougal Street was designated a landmark by the New York City Landmarks Preservation Commission in 2004.

*After crossing Third Street, the next block of Macdougal going south to Bleeker Street was once known as the Auction Block, because of the intense gay male cruising that took place here. To your right, halfway down the block on Third Street is the famed Blue Note jazz venue. Retrace your steps and continue walking west by crossing over Macdougal and Sullivan Street. Go one half block farther.

■ 84 West Third Street (between Sullivan and Thompson) Fire Patrol House No. 2 (photo above), built in 1906, was recently purchased for $4.3 million and then restored by CNN anchor Anderson Cooper for use as his residence. Among original features Cooper retained was the old firemen’s gym, which he outfitted with old-fashioned bar bells and weights. Removal of coats of exterior paint revealed the original brick, terra cotta and limestone details. Retrace your steps back to Macdougal Street.

■ 119 MacDougal, site of Caffè Reggio, an old world style coffeehouse since 1927, has been featured in many movies, notably Godfather II, and various celebrities, such as Al Pacino, have been spotted/photographed here. The claim to fame is that this was the first café in the U.S. to serve cappuccino; when founded by former barber Dominic Parisi, the only thing offered was coffee – no other beverages or food. Parisi, who never removed his hat, did not allow any other employee or patron to touch his wildly expensive, and incredibly noisy, cappuccino machine, which took his entire life savings of $1,000 to import; a large sculpted metal angel adorns the top of the appliance.

In 1959, presidential hopeful John F. Kennedy made a famous speech outside the coffee shop. When the Cavallaccis became the second (and current) owners in 1955, the angel-topped cappuccino machine conveyed, but by the 1970s it was decommissioned and placed in the street display window. Today it remains on the premises, perched atop a console along one wall. Caffè Reggio still retains its rusticated stucco walls, dark paintings, furniture, stained glass transom, lumpy pressed tin ceiling and assorted bric-a-brac (photo above) from previous decades – a neighborhood institution.

■ 130-132 Macdougal, on the East side of the street (durectly opposite Caffè Reggio), was where Louisa May Alcott wrote Little Women, while residing here in her uncle's large brick house (at right), built in 1852.










■ 117 Macdougal is now home to The Comedy Cellar, which has featured nearly every renowned American comedian, notably Robin Williams, Chris Rock, David Chappelle, all the Wayans brothers, Wanda Sykes, Howie Mandel, Jerry Seinfeld and Jon Stewart. Much of Jerry Seinfeld's 2002 documentary Comedian was filmed here. The upstairs Olive Tree Café shares the same menu, kitchen, and staff. In a previous incarnation this was home to Swing Rendevous, a 1940s-50s era lesbian bar.

■ 115 Macdougal (at the corner of Minetta Lane) is home to Cafe Wha?, a Greenwich Village mainstay that hosted Bob Dylan’s first NYC gig. Jimi Hendrix achieved early fame here, and Bruce Springsteen, The Velvet Underground, Kool and the Gang, Peter, Paul & Mary, Woody Allen, Lenny Bruce, Joan Rivers, Bill Cosby and Richard Pryor have all performed on its stage. Until 1988 it was owned by Manny Roth, uncle of David Lee Roth.

■ 116 Macdougal (East side of the street) was the former 1950s Gaslight Cafe, where Gregory Corso, Bob Dylan, Lawrence Ferlinghetti, Allen Ginsberg, LeRoi Jones, Jack Kerouac, Ray Bremser, and many others read poetry. Bob Dylan lived there for a time. Before that it was Louis' Luncheon, a hangout for writers, Ziegfield Follies chorus girls, and assorted gays and lesbians.

■ 114 Macdougal (East side of the street) is home to Esperanto Café, a former hangout of Village characters like author Joe Gould and photographer Weegee. Bob Dylan had a fight here with Andy Warhol over Edie Sedgwick; Dylan also had his only meeting with Jimi Hendrix here, when both were so stoned that not much conversation took place.

■ 113 Macdougal is the site of Minetta Tavern, a neighborhood staple since 1937. It was an Italian  trattoria/bar whose regulars customers included e. e. cummings, Joe Gould, Ernest Hemingway, Eugene O'Neill, Dylan Thomas and Ezra Pound. Named after the Minetta Brook, which ran southwest from 23rd Street to the Hudson River, Minetta Tavern was renovated in 2008 in an upscale style described as “Parisian Steakhouse meets classic NYC tavern” (photo below). A little known bit of trivia is that Reader's Digest was founded in the basement apartment of DeWitt Wallace and Lila Acheson in 1923.

■ 107 Macdougal was the former home of Rienzi’s coffee house, a James Dean hangout. There was a long-standing saying, "If a couple meets at Rienzi's they break up at Figaro's and vice versa."

■ 93 Macdougal (corner of Bleeker) was the site of the San Remo, the famous bohemian hangout of William Burroughs, Allen Ginsberg, Gregory Corso, Miles Davis, Jackson Pollock, W. H. Auden, Dylan Thomas, James Baldwin, William Styron, James Agee and Frank O'Hara. Gore Vidal once picked up Jack Kerouac here. It lost popularity because the bartenders tended to beat up the customers far too often. The setting of the beat novel Go, it also appeared as The Masque in Kerouac's The Subterraneans.

■ 184-186 Bleeker Street, at the SE corner of Macdougal, was the location of Le Figaro Café, which lasted from 1957 to 2008 (only the second floor awnings remain). It never served good food, but it was a favored spot of Jack Kerouac, Lenny Bruce and Bob Dylan. In the 1993 film Carlito’s Way, Al Pacino reminisced with Penelope Ann Miller at Le Figaro Café .

■ 92-94 Macdougal, on the east side of the street, was owned by Bob Dylan from 1966 to 1968.

■ 77 Macdougal is home to the exclusive members-only New York Rifle Club, the U.S. branch of the 19th-century  Italian shooting society known as Tiro a Segno, or "Hit the Target." Members have included Fiorella Laguardia, Enrico Caruso and Giuseppi Garibaldi. Three flags hang out front – one American, another Italian, and a third labeled Tiro a Segno, which has been at this location since 1924. Prospective members must be nominated by a current member, and there is a quota on non-Italians. Rifle shooting is done only during dinner hours in the basement gallery, which boasts three wood paneled ranges with a choice of targets. Lunch and dinner are served upstairs Tue.-Sat., and there is a dress code for men. I'm not kidding.

■ 51 Macdougal, at the SW corner of West Houston Street, is home to Something Special (above), a  coffee shop that offers mailbox and notary public services, makes keys, and sells offbeat gift items. Once we crossed Houston Street (pronounced HOW-ston), we are technically in Soho, and no longer in Greenwich Village. This shop has a small-town general store ambiance (including Lenny, the proprietor), and large glass cases that once held cakes now display jewelry, mugs, vases, boxes of crayons, clocks and a few tiny pitchers from a child’s tea set. Shelves in the center boast tag-sale fare. Many items sell for less than a dollar, relics of an earlier time when neighborhood families stopped in to buy gifts for showers or parties. Local customers have included Patti Smith, the Beastie Boys, Matthew Broderick and Sarah Jessica Parker (who insists on helping out behind the counter when she stops by). Macdougal Street ends just a few yards south of here. The adjacent building to the north, demolished for the widening of Houston Street, once housed a bar that was part of Joseph Kennedy’s rum-running business.

Retrace your steps and cross back over Houston. Cross over Macdougal to the right and continue walking along the north side of Houston for one block, turning left onto Sullivan Street. In the first block on your right is a strikingly modern condominium building, shown at right.

■ 181 Sullivan Street (between Houston & Bleeker Streets). A residential rowhouse was built on this lot around 1840. It later served as a speakeasy during the 1920s, and during this era Irving Berlin met his future wife, Ellin MacKay, here. It was called Jimmy Kelly’s, and Berlin had once worked there as a singing waiter. MacKay’s father, one of the wealthiest men on Wall Street, was opposed to his daughter’s relationship with a working class Jew, but they married nonetheless. After the 1929 stock market crash, however, Berlin was able to give his father-in-law $1 million to rescue him from financial hardship.

The rowhouse was converted into a 153-seat Off-Broadway theatre in 1960. The Sullivan Street Playhouse was home to the intimate musical The Fantasticks for 42 years, until explosive real estate values brought about its demise. The Fantasticks, which opened in May, 1960 (before Neil Armstrong walked on the Moon), holds the record for the longest run of any musical – 17,162 performances; it has since moved uptown to the Jerry Orbach Theatre at 50th and Broadway (Orbach played El Gallo in the original cast). The Sullivan Street rowhouse was demolished in 2006 and replaced by the modern building before you, which houses five residential condos.

Continue walking another half block north, then turn left onto Bleeker Street. Cross over Macdougal and continue one more block to Sixth Ave. (Ave. of the Americas for tourists). Turn right, and cross W. 4th St.; at the next corner you can pick up the subway to go uptown.