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The property, which is landmarked, used to be Germania Bank. The longtime owner-resident, who bought the building in the late 1960s and sold it in 2015 for a reported $55 million, apparently kept it cruddy-looking on purpose—the story goes that he balked at city orders to have the graffiti cleaned up because the city wouldn’t let him do the same back in the Bowery’s grittier days. Next door is the Judith Charles Gallery, a showcase for emerging artists.

       Walk farther, and on the right side past Rivington Street is The Bowery Mission. Dating to the late 1800s, this was one of the earliest mission houses for poor, homeless men. It still serves that population, and the building has some pretty features (stained-glass windows with the mission name spelled out in Old English script, mock-Tudor half-timbering). Walk a bit more to see the New Museum to the right. Bursting with cool modernity, it displays a few pieces in its windows. Look up—from this vantage point, it looks like several boxes stacked atop each other. Across the street is Bari Restaurant Equipment, established 1950. The marquee and facade resemble the grille of a vintage car.

       Continue along the Bowery past three galleries in quick succession—Sperone Westwater at #257, Soho Contemporary Art at #259, and Garis & Hahn at #263—and then come to University Settlement at the Houston Street Center. This community-services center, which operates in cooperation with the Chinatown YMCA, has a colorful mural splashed upon a wall in its yard; titled The City as a Living Body, it was created by high school students in collaboration with Groundswell, a public-art program. At Houston Street, another mural is painted at the northwest corner; for several years, this intersection has displayed changing murals painted by hip artists. (If you’re not from these parts, now is probably a good time to mention that Houston is pronounced HOUSE-ton, not like the city in Texas.)

       Turn left, walk along Houston to Mott Street, and turn left again. Like other side streets in the vicinity, Mott has many boutiques and some fairly high-end retail establishments. But this block also has two notable historical sites: The Basilica of St. Patrick’s Old Cathedral and the 14th Ward Industrial School. The school, at #256, was built in the 1880s, funded by an Astor family member for use by the Children’s Aid Society; look for the CAS in flowery script above the engraved school name. Now the building is residential. Across the street is the cathedral, which became “old” when the Fifth Avenue building was erected in Midtown. The sanctuary was dedicated in 1815, and other sections of the building were done after, although they suffered a major fire in the 1860s. The headstones in the cemetery have quite a bit of wear. Inside, the sanctuary is a bit dark, with gracious stained-glass windows and dramatic vaulting.

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      One of the marvels of Soho’s Cast Iron District

       Make a right on Prince Street. Across from the church, at #32, stands a redbrick Federal-style building from 1826. A plaque here explains that the building was originally the site of the Roman Catholic Orphan Asylum—the first mission of the Sisters of Charity, founded by St. Elizabeth Ann Seton—and later St. Patrick’s Old Cathedral School, the city’s first Catholic school. The exterior was featured in two films by St. Patrick’s alum Martin Scorsese: Mean Streets and Gangs of New York. The school closed in 2010, and the building is currently being redeveloped as condominiums.

       Go back to Mott Street and continue right (south and west). An interesting noncommercial feature of this block is the Elizabeth Street Garden, which extends back from Mott to Elizabeth Street. Among the 1,200 plantings are flowers, including lavender, daisies, and daffodils; various trees and shrubs; and vegetables and herbs. The garden also hosts such events as Tai Chi and yoga classes, poetry readings, and movie nights. (Check the website in Points of Interest for hours and an events calendar.)

       Cross Spring Street. Lombardi’s Pizza, at this corner since 1905, is generally acknowledged as the first pizzeria in the United States, a fact its web address drives home. Another old-time food haunt is the Parisi Bakery, at #198. This is one of its two neighborhood shops, in business since 1903. At Kenmare Street, look across to see two modern buildings, one of them looking like it has a transistor radio plastered on it; these are the Nolitan Hotel, a play on Nolita, or “north of Little Italy.” This portmanteau for the area (see Tribeca and Soho) was coined in the mid-1990s.

       Continue to Broome Street and make a left. The 1898 firehouse on your right at #363, Engine 55, might be one of the most likable station houses around, with its eagle bas-relief, flowing banner with the company’s name, beautiful oval windows, and metalwork. Next door is Holy Trinity Ukrainian Church, even though ghosting left behind on the facade reads CHURCH OF SAN SALVATORE (that congregation left). Walk in the other direction, across Mott Street, to 375 Broome, which has several gargoyle-y faces with rather dramatic facial hair carved into window decorations, plus one near the roof that’s downright spooky.

       Make a left at Mulberry Street and stroll beneath the WELCOME TO LITTLE ITALY sign that hangs across the road. Check out the many Italian eateries as you walk to Grand Street. Cross Grand to see the Italian American Museum, on your right. Then cross Mulberry and walk on Grand. To your right, Ferrara makes really fine cannoli. On the other side of the street, check out a few of the area’s best (and longest-lived) Italian-food shops: DiPalo, Piemonte Ravioli, and Alleva. As a cheese fan, I was smitten by a mozzarella ball I spotted in Alleva; I took it home and it was quite tasty.

       Head back across Mulberry and make a right at Centre Market Place, a block that comes out of Baxter Street and was named for the nearby Centre Market, now long gone. On the right are townhouses in various colors. Note that street numbers run consecutively here, from 1 to 8, not even on one side and odd on the other.

       When the block ends at Broome, make a left and take a good look at the big fancy building that’s also to your left. This block-long entity is 240 Centre St., which was New York City police headquarters from 1909 to 1973. In 1988, it was converted to luxury condos. (The NYPD is now based near City Hall; see Walk 5.) The dome is the loveliest part, with its clocks, columns, and cupola. This is definitely a building to admire both up close and in full. Walk around it via Broome Street and then a quick jog left on Centre Street.

       Make a right onto Grand Street again.

       At Broadway, make another right. You’re now in Soho (“south of Houston”), known for its many cast iron–front buildings. (Try this cool trick: Take out a small magnet, walk up to one of these buildings, and affix. Voilà!) Many of these structures were erected in the 1880s and 1890s, some before, some into the early 1900s. By the 1950s, this district was nicknamed “Hell’s Hundred Acres” because of its many sweatshops and factories (and the accidental fires that frequently started in them). Some historic buildings succumbed to the wrecking ball, but preservationists fought hard to save many others, and in the 1960s and 1970s artists of various stripes discovered they could set up lofts in the old industrial spaces quite cheaply. Now, of course, Soho is very expensive; in fact, it nearly rivals Madison Avenue on the Upper East Side for posh designer shops. Below I make note of my favorite buildings along this stretch of Broadway, but there are many others worth a look and a photo.

       First, at #462, see the International Culinary Center on your right, along with its Michelin-honored student restaurant, L’Ecole. The building in which they’re housed dates from 1879 and takes its architectural cues from the French Renaissance. Narrow #472, an apartment building, has lovely lacelike ironwork. Impressive #478–482 (a clothing boutique) has intricate work between its pilasters and windows. The building at #486 is made of red brick but has attractive darker banding on the top floors.

       Continue along Broadway, crossing Broome Street, and gaze at #488, a feast of pillars and arches. The building at #504 is likewise an arch festival (with a Bloomingdale’s!), while #508 and #510 have elegant moldings at their rooflines, both topped with rounded pediments. After you pass Spring Street, #532 has opulent Beaux Arts touches. Narrow #540 has vaguely Celtic flourishes around the windows; also note the “1867” at the roof. Next door, at #540–542, there are three caryatids to catch your eye, each slightly different, near the roof. Across the street, massive #555 reads CHARLES BROADWAY ROUSS. Charles Baltzell Rouss operated

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