Tenements, Tales, and Tastes of New York’s Lower East Side with Urban Adventures NYC


New York City is The City That Never Sleeps and with so much to offer, wading through all the things to do in NYC to find the right fit for your visit can be overwhelming. Where do you begin - food, history, landmark architecture, Broadway? Our favorite would be the New York food tours, since the biggest draw for us as foodies is of course, the food! We all know food is at the heart of every culture, and if you’re looking for the best ethnic food NYC has to offer — the kind that’s been here for generations — visit the parts of town with the richest history - Brooklyn, Harlem, Hell’s Kitchen, the Lower East Side. The foods here have history and culture in every bite, which makes NYC one of the best destinations in the country for foodies.

On our recent visit to Manhattan we took a tour with Urban Adventures NYC on their “Tenements, Tales, and Tastes” of the city’s Lower East Side. Although we visit NYC at least once a year, we had never explored this part of the city outside of Chinatown and Little Italy. This tour highlighted the landmark buildings and history of how things developed in this unique part of Manhattan. As second-generation Italian-Americans, we were especially interested since our grandparents immigrated from Italy through nearby Ellis Island at the turn of the 20th century. And bonus — there’d be food! This tour includes visiting a few places along the way that still serve the authentic and delicious foods brought here by the original immigrants. We couldn’t wait to get started.

Tenements & Tales

Stroopwafels from The Good Batch, a Brooklyn bakery

If you’re unfamiliar with what a tenement is, these buildings were notorious narrow five to seven story apartment buildings and a hallmark of the New York City’s Lower East Side neighborhood. They were cramped, dirty, dimly lit if lit at all, and indoor plumbing and ventilation were virtually nonexistent. By 1900, approximately 2.3 million people or nearly two-thirds of the city’s population were living in tenement housing. Unscrupulous tenement owners discovered that what started out as two rooms per floor, and already incredibly overcrowded, could be divided into 4 rooms or more. They would crowd even more people into each floor to raise the rent and increase their profits. If you’re interested in knowing more, we highly recommend a visit to the Tenement Museum, one of the most fascinating glimpses of this part of New York and American history.

Our tour was in January, on a cold and rainy day, so the smile and enthusiasm of our guide, Mary Hannah, was most welcome. Our starting point was at the fountain in City Hall Park in lower Manhattan. She presented each of us (there were 4 in our group) with a little fuel to get the walk started, Stroopwafels from The Good Batch, a Brooklyn-based bakery. This sweet Dutch confection is a hand-pressed waffle-like cookie filled with a nutmeg flavored caramel.  Delicious. Mary Hannah did not waste any time at getting the tour started. Because we were in City Hall Park the first building on the tour was, well, City Hall.

New York City Hall, NYC

As we walked, Mary Hannah talked about the early architecture and settlement of the Lower East Side. While we didn’t go inside them, we learned about or saw each of the following places:

City Hall

Dating to 1812, this is one of oldest city halls in the country. It’s  an imposing building with its great rotunda and corinthian columns. In 1966 City Hall was designated as an individual landmark by the Landmarks Preservation Commission. Its beautiful central rotunda was named an interior landmark in 1976.

African Burial Ground National Monument

African Burial Ground National Monument

African Burial Ground National Monument

In the early 1990s while excavating for a new federal office building, construction workers discovered the remains of 419 Africans. Research showed that in the 17th and 18th centuries this unmarked cemetery was a burial ground for hundreds of Africans. It has been estimated that 15,000 Africans were buried in this 6.6 acre plot of land. In 1991 the African Burial Ground project was started to create a memorial on this sacred burial ground. The site was designated a National Historic Landmark in 1993 and a National Monument in 2006. We were unable to go inside and only saw the monument from the outside due to construction and repairs. In 1993, the African Burial Ground and the Commons, which includes City Hall and the surrounding park, was designated a Historic District by the City of New York.

David N. Dinkins Municipal Building

Surrogate's Courthouse, Hall of Records, New York City

Surrogate's Courthouse, Hall of Records, New York City

Opened in 1914, this really large (for a municipal building) rises 25 stories in the main section with a golden gilded statue, Civic Fame, on top. It has a long open plaza along with Corinthian columns and is designated as a New York City Landmark. It’s existed under several names over the years but most recently as the David N. Dinkins Municipal Building. We didn’t go inside. That’s not part of the tour. But it is a big and busy place.

Surrogate’s Courthouse

Another magnificent NYC building built in the Beaux Arts style and opened in 1907. High above the entrance are statues of people who are part of the history of New York, such as the colorful Peter Stuyvesant. Also known as the Hall of Records, Surrogate Courthouse is a designated New York City Landmark.

Tweed Courthouse

This one we found particularly fascinating especially if you’ve seen the movie “Gangs of New York”. Finished in 1881 this is the old New York County Courthouse and the legacy of the infamous Tammany Hall boss, William M. Tweed. Seems he used the construction project to embezzle large sums of money from the construction budget for himself and his cronies. Tweed’s scheme was eventually found out, and ironically, he was tried, convicted, and sentenced in an unfinished courtroom in the building. In 1984 the courthouse was designated as a New York City Landmark and is listed on the New York State and National Register of Historic Places.

Foley Square

A lovely small park in the heart of New York City's civic center that is named for Founding Father, Thomas Paine. The park was once part of a swamp that was, ironically, surrounded by three British prisons for revolutionaries. The area has a violent and troubled history. For part of the 19th century, it was part of one of the most notorious slums in the country, Five Points. Crime and corruption savaged this community of mostly poor Irish immigrants. You have to see “Gangs of New York”. Here also is the New York City Supreme Court Building where episodes of the television series “Law and Order” were filmed using the outside steps.

Collect Pond

Collect Pond Park, New York City

Collect Pond Park, New York City

At one time this was a large spring-fed pond. During the 17th and 18th centuries, it was a parklike setting for picnics and ice-skating and was still clean enough to provide the area’s drinking water. As things would have it, by the early 19th century the surrounding overcrowded conditions had turned the pond into an open sewer. In their short term wisdom the local authorities decided to fill the pond turned sewer with dirt from a nearby hill. By 1811 the filling of Collect Pond was complete, and a neighborhood known as Paradise Square was built on top of where the pond had been. No good deed goes unpunished. To build on top of fill that was placed over an active spring proved to be folly, and in the 1820s Paradise Square began to sink. But that wasn’t all, the neighborhood began to stink, literally, and the most affluent residents had no choice but to leave. By the time the 1830s rolled around, Paradise Square had become the infamous “Five Points”.

Five Points 

An ugly but interesting part of the 19th century history of NYC, this is now the location of Chinatown.  Five Points took its name from the intersection of four streets - Anthony, Cross, Little Water and Orange. Where they merged formed an irregular intersection with five corners, hence the name Five Points. Overcrowded slums, squalid living conditions, fear spread by gangs of Irish immigrants, and rife with crime and disease, Five Points gained a reputation around the world for its unimaginable conditions. Today that area has been built over with professional and court buildings and the streets no longer exist as they once did to form the Five Points. We actually found this bit of history fascinating and will have to read more about it. Photos courtesy Wikipedia Commons.

“27 Club” Mural

On a wall at at the corner of Rivington and Forsyth Streets is an incredible mural by Brazilian artist Eduardo Kobra. The mural is composed of five faces of musicians who sadly died at the age of 27. Janis Joplin, Kurt Cobain, Jim Morrison, Jimi Hendrix, and Amy Winehouse are now memorialized as what has become known as the “27 Club”.

The "27 Club" mural, street art in New York City

Rivington Street Synagogue

Rivington Street Synagogue, New York City

A part of the Jewish history of the Lower East Side, this old tenement building at 58-60 Rivington dates to 1904 and was originally designed in the Moorish revival style. It had fallen into severe disrepair and had become a flop house for homeless people and drug addicts. In 1979 artist Hale Gurland purchased the building to preserve its place in the history of the Jewish Lower East Side, turning it into studios and residences for local artists. He completely redid the interior, but chose to leave the building’s beautiful facade as close as possible to the original.


In between learning the history of the Lower East side, there were noshes of the amazing food that’s been made here for generations, and before that in the respective old countries. These were our favorite parts of the tour!

The Fried Dumpling 

STOP 1: We couldn’t read the Chinese menu, but a lady at the rear of this small stand-up dumpling joint was busy making dumplings completely by hand. I love places like these — so authentic and some of the best Instagrammable food spots in NYC, especially when they’re making dumplings! Mary Hannah placed the order and in a few minutes we were enjoying pork and chive dumplings steamed and as pot stickers. They also sell bags of frozen dumplings to take along. Wish we would have had a place to keep them because I would have bought more! 106 Mosco Street, NYC


STOP 2: In a small corner of what’s left of Little Italy is the Alleva Dairy, the oldest cheese shop in America making their own authentic ricotta and mozzarella. If you love Italian cheeses you have to make this a stop during your visit, it was insanely good. But they have more than cheese. They feature many Italian delicacies like  prosciutto, salamis and provolone. In the mood for lunch? Try the freshly made arancini, eggplant parmesan, or one of our favorites, their Italian sub. It’s all excellent. 188 Grand Street, NYC

Ferraras Bakery

Ferrara's Bakery, NYC

STOP 3: Although Ferrara’s wasn’t officially a stop on the tour, Mary Hannah chose it for a ‘pit stop’. It’s conveniently across the street from Alleva. We’d been walking in the cold and rain so it was time for a hot coffee, a pastry, and yes the restroom. Ferrara’s has been in operation since 1892 and is a perennial favorite of ours.

We just can’t pass up the Italian pastries like cannolis and sfogliatella, and yummy soft pignoli cookies. They ship anywhere, just sayin! 195 Grand St, NYC

Yonah Schimmel Knish Bakery

STOP 4: Not sure what a knish is? You are in for a real treat. Simply put, a knish is a traditional Eastern European snack food brought here by Jewish immigrants. In its simplest form a knish consists of a filling of potato and onion or sometimes buckwheat (kasha) wrapped with a thin layer of dough that is baked. There are other additions and fillings on the menu like spinach, broccoli, cheese, and mushrooms and they are always baked. The Yonah Schimmel Knish Bakery has been in operation since the 1890s and remains one of the few distinctly Jewish restaurants on the Lower East Side. 137 East Houston Street, NYC

Loreley Restaurant & Biergarten 

LAST TASTING STOP 5: Our last stop of the day, sitting down inside where it was warm but the beer was cold. Loreley has a fairly extensive menu based on German cuisine and is modeled after the ‘Brauhaus”in Cologne, Germany. Loreley boasts the largest heated outdoor beer garden on the Lower East Side and the German beer selection is very good. When you visit here be sure to order a warm freshly baked soft pretzel or maybe two. They come with a German mustard dipping sauce and go great with any beer on the menu. Highly recommended for an afternoon break. 7 Rivington Street, NYC

What We Loved

  • Our guide Mary Hannah was very knowledgeable, and even with the rain kept us at a comfortable pace for the 3 hour tour.

  • Food stops were well-chosen and added to the fun of the experience.

What We Didn’t

  • Wish we could have gone inside at least a few of the landmark buildings, for example to see the beautiful architecture of the Hall of Records in the Surrogate’s Courthouse.

  • Taste samples were modest: each person on the tour had 2 fried dumplings, a small mozzarella ball and small taste of prosciutto, half a knish, a 5 oz beer, and a piece of soft German pretzel. For 3 hours, we felt it could be enhanced.


The Tenements, Tales, and Tastes tour is a delightful combination of Lower East side walking tour and Lower East side food tour. It’s not the best food tour NYC has to offer — it’s not really a food tour — which is important to know going in. It’s more of a ‘History Tour with Tastings’. If you’ve followed us on other food tours we’ve taken you know we’ve been on a few that offer a lot of food throughout the tour, like the Italian Days tour food coma for example. If that’s what you’re expecting, you should look at other dedicated food tours NYC has, and there are many good ones.  There’s also no stop at the Tenement Museum, which of course would take hours just exploring that on your own.


But if you’ve never been to the Lower East Side and want to learn more about its fascinating history, then we highly recommend the ‘Tenements, Tales, and Tastes’ tour with Urban Adventures.  You’ll learn how this area has changed over time with each new influx of immigrants of different nationalities.  A tour should be more than just walking around. It should be fun, interesting, and entertaining, right? This tour is all that. And stopping at some of the original Lower East Side eateries to sample ethnic foods was a real treat. The next time you’re in the city, if you have the time, take this tour.  

If You Go

  • Length of tour: 3 hours

  • Cost: $79 per person, which includes a local English-speaking guide and several tastes of different ethnic dishes