Greenwich Village and SoHo: Second Lives, from Courthouse to Cast Iron

4.60·10 Stops·90 minutes·2.9 km

Walk from Jefferson Market's clock tower past the Stonewall Inn, Washington Square Arch and the old folk clubs of MacDougal and Bleecker into SoHo's cast-iron streets, ending at the glass-fronted Little Singer Building.

Start · Jefferson Market Library: The Courthouse with a Fire Tower

Directions

Stops

1
Jefferson Market Library: The Courthouse with a Fire Tower
A Victorian courthouse whose tower was built as a fire lookout. Neighbours saved it, starting with its four stopped clocks, and it has been a library since 1967.
2
Stonewall Inn: Stables, a Raid and a Monument
Two 1840s stables became the Stonewall Inn, where a 1969 police raid sparked days of protest. The little park opposite is now a national monument.
3
Washington Mews: Stables Behind the Row
A cobbled lane of old stables now lived in as houses. They served the grand 1830s brick houses of the Row, whose fronts hide a 1939 building.
4
Washington Square Arch: A Party Prop in Marble
A temporary plaster arch rebuilt in marble by popular demand. The lawn around it began as a burial ground for the poor.
5
MacDougal Street: Stables, Garages and Folk Clubs
A 1907 stable became the club where young Bob Dylan played. Opposite stands a matched row of old tenements, the Gaslight among them.
6
Bleecker Street: A Hotel Where Every Room Had a Window
Ernest Flagg's 1897 hotel for working men gave every room a window. Down the block a club fills a town house with its front steps removed.
7
Prince Street: Into Cast-Iron SoHo
Artists turned SoHo's empty warehouses into lofts in the 1960s. Margot Gayle's campaign helped win the district its protection in 1973.
8
Greene Street: The King of Greene
An 1873 warehouse dressed as a Paris palace in painted iron. Its permit called for seven storeys, but the records list five.
9
Haughwout Building: A Venetian Palace in Iron
This 1857 iron store had New York's first passenger elevator for shoppers. A planned expressway nearly took the whole street.
10
Little Singer Building: Flagg's Front of Glass
Ernest Flagg's twelve-storey front of glass and iron tracery from 1904. Nearly fifty years after the Haughwout, the iron stops pretending to be stone.

Details

Best Time to Visit

A weekday morning or early afternoon is calmest, and Tuesday to Sunday lets you step into the Stonewall visitor center, open 10 a.m. to 4 p.m. and closed Mondays (checked 30 September 2026). Washington Mews is open by day only. SoHo's sidewalks are at their most crowded on weekend afternoons, and MacDougal and Bleecker come alive after dark.

Pro Tips

•Jefferson Market Library is a working New York Public Library branch and free to enter; check opening hours on nypl.org before you go (not confirmed for this walk, 30 September 2026).
•The Stonewall National Monument Visitor Center at 51 Christopher Street is free, Tuesday to Sunday, 10 a.m. to 4 p.m., closed Mondays (National Park Service, checked 30 September 2026).
•Detour to the Queen of Greene Street: from the King, carry on down Greene Street past Broome and Grand. The Queen is at 28 to 30 Greene, between Grand and Canal, on the same side as the King, six storeys with a mansard roof. Then come back up to Broome Street to rejoin the walk at Broadway.
•In Washington Square Park, James Jackson's 1799 headstone is on show in a window of the Park House, near the Sullivan Street side of the park.
•The walk ends a short way from the Prince Street subway station on Broadway.

Safety & Precautions

•As of the Washington Square Park Conservancy's update of 14 August 2026, the Washington Square fountain was fully turned off for plumbing repairs; expect a dry basin.
•Washington Mews is a private New York University street, open by day only. The stop works from the public sidewalk on the west side of Fifth Avenue, opposite the gate; do not go in after hours.
•Houston Street is wide and busy. Cross it only at a marked crossing and with the signal.
•In 2026 building permits were active at 561 Broadway (the Little Singer Building) and at 25 Washington Square North, so expect possible scaffolding or sidewalk sheds.
•The Stonewall Inn is a working bar and the visitor center sits beside it; take photos from the sidewalk and keep the doorway clear.
•SoHo sidewalks get very crowded, especially at weekends; step aside to listen rather than stopping in the flow.

Read our safety guide

Travel advisory: Exercise Normal Precautions (Level 1).

U.S. Department of State

Gallery

Jefferson Market Library: The Courthouse with a Fire Tower

Stonewall Inn: Stables, a Raid and a Monument

Washington Square Arch: A Party Prop in Marble

MacDougal Street: Stables, Garages and Folk Clubs

Bleecker Street: A Hotel Where Every Room Had a Window

Haughwout Building: A Venetian Palace in Iron

Little Singer Building: Flagg's Front of Glass

Read the walk

The full story of Greenwich Village and SoHo: Second Lives, from Courthouse to Cast Iron, in words. Prefer to listen? Play it narrated, from home or on location.

Introduction

New York, in the United States, keeps some of its most crooked streets on the lower west side of Manhattan. In Greenwich Village the lanes refused the city grid two hundred years ago and still run at odd angles. Just south of them, SoHo is a district of iron-fronted warehouses that was once widely written off as a slum.

Almost every building on this walk was made for one job and now does another. A courthouse became a library. Horse stables became a bar, and a lane of houses. A hotel for poor working men became apartments, and warehouses built for goods became artists' studios, then shops. The outside usually still shows the first job, if you know how to read it. Most often, the windows give it away.

Over ten stops and a little under three kilometres, the walk runs from Jefferson Market Library past the Stonewall Inn, through Washington Square, along the old coffeehouse blocks of MacDougal and Bleecker Streets, and into the cast-iron streets of SoHo, ending on Broadway. It takes about an hour and a half at an easy pace.

Two people keep turning up. Margot Gayle was a Village neighbour who started by fighting for a stopped clock and went on to help save SoHo. Ernest Flagg was an architect who cared about light, and he designed two of the buildings on this walk, one of them its last stop.

1. Jefferson Market Library: The Courthouse with a Fire Tower
Welcome to Greenwich Village, and to Jefferson Market Library, the red brick building across the avenue, with the tall clock tower at its far corner, on Sixth Avenue and West Tenth Street.
Start at the top of that tower. It looks like a church spire, but the city's landmarks report says the top was designed as an enclosed fire lookout, with an enormous alarm bell, and a four-faced clock above the bell. The block below is a triangle, and the tower rises at its sharp end, in the report's words, like the prow of a fantastic ship.
Now the walls. Red brick banded with pale stone, steep gables, stained glass, and on the Sixth Avenue front the seal of the city. The report says the building positively glows with colour. It went up between eighteen seventy-four and eighteen seventy-seven as a courthouse, and in the eighteen eighties a poll of architects placed it fifth among the most beautiful buildings in the country.
Then the courts moved out. The city used the building for other things, a police academy among them, and the four clocks stopped. In the late nineteen fifties a neighbour, Margot Gayle, set out to get them going again. A small fight over a clock grew into a fight for the whole building, and around nineteen sixty the clocks were running again. In nineteen sixty-seven, after steady pressure from Village groups, the old courthouse opened as a branch of the New York Public Library. It still is one, and free to walk into.
It was made for judging and for watching, it now lends books, and its tower still looks exactly like a lookout. Remember Margot Gayle. She comes back at the end of the walk, in SoHo.
Cross Sixth Avenue at the lights and follow the route into the crooked side streets. Next, a small railed park and a famous bar.
2. Stonewall Inn: Stables, a Raid and a Monument
Walk on along the railings of the small park, Christopher Park, and stop a few steps short of its gate. Across the street is the Stonewall Inn, and next door to it, at number fifty-one, the visitor center of Stonewall National Monument. It is free to visit, and the details are on this stop's card.
Read the front of the bar. A ground floor of red brick, with round-arched doorways and small windows set high above a tall base. The building began as two horse stables of the eighteen forties. A bakery came later, then in nineteen thirty the two were joined behind one front, and from nineteen thirty-four it was a restaurant called the Stonewall Inn. In March nineteen sixty-seven it reopened as a gay club. The owners painted the windows black and put plywood behind them, and the city's landmarks report says small windows, high sills and dark glass were typical of gay bars of the time.
At about one twenty in the morning on Saturday the twenty-eighth of June, nineteen sixty-nine, police raided the bar. The crowd outside fought back, and protests went on, with quiet nights between, for five days. Who started it is not known, and historians have taken apart many of the stories told since. One thing is clear: the streets helped. In the early eighteen hundreds residents had refused to straighten these lanes into the city grid, and the crowd used them to slip round a corner and regroup behind the police lines.
Inside the railings, the white figures, two men standing and two women on a bench, are a sculpture called Gay Liberation. It was commissioned in nineteen seventy-nine and installed only in nineteen ninety-two. In twenty sixteen this little park became Stonewall National Monument.
Follow the route back across Sixth Avenue at the lights, toward Washington Square. Next, a lane of old stables.
3. Washington Mews: Stables Behind the Row
Walk on up Fifth Avenue and stop on this sidewalk, opposite the iron gate of Washington Mews, the cobbled lane across the avenue. The lane is a private street used by New York University and open by day, so this stop works from here.
Look along the lane at the low houses, most of them two storeys. The landmarks report says the name Mews tells you most of them were stables, and on one side of the lane that is still easy to read. Look for wide arched openings, some of them filled in, where carriages went in. On number eleven the report counts two bricked-up stable doorways. On number sixteen, a brick stable of eighteen eighty, a curved-top window sits where the hay-loft doors used to be. Stables first, homes now, and the bricks still say so.
Whose horses lived here? Those of the big houses across Fifth Avenue, facing the square. They are called the Row, and you will see their fronts on the way back to the park. They went up around eighteen thirty-three on land owned by Sailors' Snug Harbor, a charity for retired sailors, and the landlord controlled them down to the front door. Leases of eighteen thirty-one demanded houses at least three storeys high, in brick or stone, set back twelve feet from the street, and finished in a style the trustees approved. The result was red brick, white marble steps and one long iron railing, and the report calls it the prototype, in this country, of the monumental Greek Revival row house.
In nineteen thirty-nine the owners kept the fronts of numbers seven to thirteen and built a low apartment house behind them, with its entrance on Fifth Avenue, the avenue in front of you. The faces are from the eighteen thirties. Behind them, almost nothing is.
Follow the route back to the square and past the arch. Next, the park itself.
4. Washington Square Arch: A Party Prop in Marble
Walk on past the arch into Washington Square Park, and stop between the arch and the round fountain basin. Then turn back to face the arch. White marble, more than twenty metres tall, a version of a Roman triumphal arch. In the opening, the underside of the vault is a grid of…
Full narration for this stop unlocks with the tour.
5. MacDougal Street: Stables, Garages and Folk Clubs
Walk on down MacDougal Street, and stop opposite the corner of Minetta Lane. Across the street, find the low, wide front squeezed between taller buildings, with stairs going down to a basement club. That is the club called Cafe Wha, at number one fifteen, and its shape gives…
Full narration for this stop unlocks with the tour.
6. Bleecker Street: A Hotel Where Every Room Had a Window
Walk on along Bleecker Street to the corner of Thompson Street, and stop there. Across the street stands a big pale block, ten storeys of light brick and limestone. This is Mills House Number One. Its architect was Ernest Flagg, and this is the first of his two buildings on the…
Full narration for this stop unlocks with the tour.
7. Prince Street: Into Cast-Iron SoHo
Walk on to the corner of Prince Street and West Broadway, and stop there. You have crossed into SoHo. Houston Street, the wide road you just crossed, was widened between nineteen fifty-seven and nineteen sixty-three, and it works like a moat. SoHo simply means South of Houston.…
Full narration for this stop unlocks with the tour.
8. Greene Street: The King of Greene
Walk on down Greene Street, and stop on the sidewalk opposite numbers seventy-two to seventy-six, the long, deeply modelled front across the street. People call it the King of Greene Street. It looks like a palace in Paris. It is a warehouse, finished in eighteen seventy-three,…
Full narration for this stop unlocks with the tour.
9. Haughwout Building: A Venetian Palace in Iron
Walk on along Broome Street to the corner of Broadway, and stop there. Diagonally across the junction, on the far corner, stands a five-storey palace of iron, painted a pale cream. It is the Haughwout Building, from eighteen fifty-seven. Count the windows. The same arched…
Full narration for this stop unlocks with the tour.
10. Little Singer Building: Flagg's Front of Glass
Walk on up this side of Broadway, and stop opposite number five sixty-one, across the avenue: a narrow twelve-storey front made mostly of glass and laced with iron. This is the Little Singer Building, built in nineteen oh three and nineteen oh four for the Singer sewing machine…
Full narration for this stop unlocks with the tour.

Listen to this walk

Greenwich Village and SoHo: Second Lives, from Courthouse to Cast Iron

Stops