What we're about


This is a group for people either new to New York City, or have called the city home for awhile and are interested in discovering new neighborhoods and learning more about the city's fascinating history, architecture and culture. Most of our activities are professionally-guided walks of 3 - 5 miles within a NYC neighborhood that has distinct and unique qualities. They usually last from 2 to 4 hours. We sometimes have an optional social hour afterwards for a meal and/or a beverage at a local restaurant (except during COVID-19 for safety reasons). Barring any COVID-19 restrictions, during the summer months we usually combine a walk with a free outdoor concert, often in the evenings. During the winter we'll have shorter outdoor walks coupled with a museum visit ( if permitted under COVID-19 guidelines for indoor activities).

I also organize theme tours to add some spice and variety to honor holidays or famous New Yorkers. Our events are usually free with a voluntary donation of a dollar or two. When we have museum visits there may be an admission charge.

I started this group because I am a native New Yorker and have a successful dual career as a professional tour guide and real estate agent and I am affiliated with the prestigious Corcoran Group, which was started by pioneering entrepreneur Barbara Corcoran. I had a 25-year career as a social worker, including work in the South Bronx and throughout Brooklyn, and served on the teaching faculty of Columbia University, Fordham University, New School University, Hunter College and NYC Technical College.

I have a B.A, in English and a Master's Degree in Social Work, and have also been an exhibited visual artist with a focus on experimental and landscape photography. I love to introduce people to new neighborhoods and explore their past, present and future and also welcome the opportunity to learn from others. With the fast-pace of life here it is easy to overlook the hidden treasures and iconic buildings that we pass by every day. While I have a repertoire of touring a good 70 neighborhoods, I especially love Harlem (where I spent my formative years) due its many different areas, amazing history and beautiful architecture. Other favorites include the West Village, Lower Manhattan (where the City's history began), Flatiron/Gramercy, Upper West Side, Brooklyn Heights, Fort Greene/Clinton Hill, Long Island City, the East Village and Washington Heights.


Your participation in the activities of Exploring NYC History and Neighborhoods acknowledges that you are solely responsible for your own assessment of your abilities and your physical fitness and health to participate in that activity.

As I have resumed in-person tours, proof of full vaccination is required to participate. You should also be physically fit and be able to walk several miles at a moderate pace. Given the added importance of social distancing during the COVID-19 pandemic, it is also important that participants are capable of being keenly observant of their surroundings.

There are always inherent risks that can cause or lead to injury, property damage, illness *including the coronavirus*, emotional trauma, disability or death to participants or others when participating in an activity. Some, but not all of these risks include: hazardous and unpredictable ground, water or weather conditions, traffic conditions, misjudgments made by the leader or a participant, the potential that a participant or others may act carelessly or recklessly, etc. etc.

Hank Orenstein and Exploring NYC History and Neighborhoods cannot assure a participant’s safety or eliminate any of these risks. The participant is voluntarily participating in our activities with knowledge of these risks, and therefore the participant must accept full responsibility for the inherent and other risks (both known and unknown) of these activities, and for any injury, damage, death or other loss suffered by the participant.

By joining any event conducted by Hank Orenstein/Exploring NYC History and Neighborhoods, the participant agrees to release and indemnify Exploring NYC History and Neighborhoods and/or Hank Orenstein with regard to any and all claims, liabilities, suits, or expenses (including reasonable costs and attorney’s fees) for any injury, property damage, illness including the coronavirus, emotional trauma, disability or death to participants or others in any way connected with the participation in an activity.

Upcoming events (4+)

The "You Don't Have to Be Jewish" Lower East East Side Tour

Needs a location

RSVPs begin on 3 weeks prior to the tour on Saturday, September 17th at 10am. There is a limit of 30 people with up to 10 spaces set aside for new members and first and second timers. If you are in one of these categories and you land on the waiting list feel free to email me to request a spot.

TOUR IS FREE WITH OPTIONAL DONATION. Co-leading this tour with me is group member Richard Soden, who is also a licensed NYC guide and a long-time resident of the Lower East Side.

To bring: Proof of Full Vaccination; a mask.

Arrive early to use the restroom inside the Essex Market. It is also fun to check out the various food purveyors and to get coffee and a bite to eat.

This is the season of the Jewish high holidays and I am appropriately offering this tour in the wake of Rosh Hashanah and Yom Kippur and Sukkot which begins on Sunday evening October 9th. At one time the Lower East Side was the 2nd largest Jewish community in the world and we'll cover that rich history.

When my paternal grandfather's family arrived in New York from Eastern Europe in 1905 they settled in the Lower East Side among the countless numbers of other immigrants who came to New York in search of economic opportunity, political and religious freedom. They worked as street peddlers selling clothing off of pushcarts.

The Lower East Side historically was the center of immigrant life for hundreds of thousands of people starting with people from Germany in the 1840's and then Italians, Jews and people from all over Eastern Europe, Greece and Russia. While the neighborhood has certainly changed and has attracted young people from all over the world in recent years, the area has maintained its diversity and remnants of its past which can be experienced by walking past the many tenements, religious buildings and even some businesses that have been in operation for generations.

The Lower East Side is where New York's garment industry began in the 1800s and where the public health movement in the United States was born, arising from the devastating living conditions among the poorest immigrant families.

Stops during the tour include synagogues that are still in use, those that have been converted to other functions such as art galleries, churches, and event spaces as well as bathhouses, restaurants, movie theaters, and many more as we discuss the transformation of the neighborhood.

We'll be sure to pass the extraordinary Lower East Side Tenement Museum and store, where you can pick up information about the tours and educational programs offered there. We'll also experience vibrancy of the "new" Lower East Side -- and its expanding visual art scene, restaurants night life and new housing.

The tour ends where we began at the Essex Market.

Cheers from your organizer and guide!


Indigenous People's Day Tour of Lower Manhattan!

Needs a location

Note start time has been moved to the afternoon at 2:00pm due to work obligations in the morning. Also gives time for people to have lunch beforehand. Optional afterparty at a local establishment.

Space set aside for new members and first timers. ***If this would be your first time attending one of tours and you land on the waiting list feel free to email me to request a spot. *** The tour and museum are free with a voluntary contribution at the end for your leader.

To bring: Proof of full vaccination, a mask (wearing during the tour is optional). You may want to bring a snack as we will have a break during the tour.

MEETING PLACE: Outside the National Museum of the American Indian (pictured above). I suggest arriving at least 45 minutes beforehand by 1:15pm to get a taste of the museum and use the restroom. The building is part of the Smithsonian museum and has requires and efficient security check that includes metal detectors. It also a historic landmark and one of NYC's most magnificent public buildings inside and outside. Be sure to visit online before you go:

This tour is especially great for people new to New York City as we cover a lot of our early history.

The Lenape Indians inhabited the area we call NYC centuries before the Europeans colonized the area began to colonize the area in the early 17th century. The spirit of Indigenous People's Day to acknowledge the resilience, ingenuity, creativity, culture and strivings of indigenous people's despite centuries of racism, discrimination, forced removals and essentialy genocide.

American Indians have a sophisticated understanding of ecology and taking care of the land along with their great respect for the forces of nature and the bounty of the earth. The Iroquois tribes of upstate New York also influenced the early women's rights movement of the mid-1800's due to the leadership roles of Indian women. In the 20th century Mohawk Indians from New York helped to build our skyscrapers and bridges.

The tour will focus on sites associated with Native American presence in Lower Manhattan. Given the rich and complex history of what we call the Financial District, I will also weave in the key historic touchpoints of colonial New York including the chain of events that led to the American Revolution, NYC's role as America's first Capital, and the role of Wall Street. I will also talk about current efforts by Lenape Indians to reclaim their local heritage and history.

The tour will end convenient to Canal Street, Tribeca, Chinatown and Little Italy and abundant public transportation options.

Note: NYC still honors the 2nd Monday of October as Italian Heritage Day/Columbus Day and there has been some controversy about this. The NYC Department of Education and other entities have attempted a compromise by also acknowledging the many contributions of Italian-Americans as opposed to Columbus who forced indigenous people into slavery and brought disease and devastation. I will devote some time on the tour to Italian American Heritage as it relates to NYC.

On Sunday, October 9th and Monday October 10th at Randall's Island Park there will be a celebration of Native American Culture through song,dance, works of art, food and more!

Your organizer and guide,


The Amazing 3 Squares Tour: Union Square, Gramercy Park & Madison Square.

RSVPs open Friday, October 7th at 6pm.

I cancelled the original tour on Saturday, October 1st due to rain forecast and rescheduled it for Saturday, November 5th and added a 2nd option for Friday, October 14th at 3:00pm. Those who were registered for October 1st have been automatically scheduled for Saturday, November 5th, including the waiting list.

For this new date, priority is given to those who were on the waiting list or the going list for October 1st or who wish to switch their RSVP for Oct. 15th. The people who see on the going list are those who have made that request. You can do so until RSVPs open to our entire membership next Friday.

The tour is free with voluntary donations appreciated. Note that there is a limit of 30 people people with up to 10 spaces set aside for new members and first timers. New members or first timers: If you land on the waiting list feel free to email me to request a spot.

To bring: Proof of full vaccination, snacks if you like (we'll have a break).

Total walking distance: approximately 3 miles.

Tour Overview:

This is one of my favorite tours for New York history, architecture and stories! We'll start out at Union Square with a visit to the four freedoms monuments (Lincoln, Gandhi, Washington and Lafayette). Union Square was at one time the city's most popular entertainment district and was used for parades, marches and political rallies (and still is on occasion).

At Gramercy Park, one of NYC's first planned neighborhoods in the 1830s, we'll learn about the actor Edwin Booth, who founded The Players Club (and brother of the LIncon's assassin John Wilkes Booth), and the see the former mansion of NY State Governor Samuel J. Tilden. Tilden has figured prominently in history not only as because he helped establish the NY Public Library but as a candidate for President in whose election defeat in 1876 is perhaps the most controversial in American History (along with Bush v. Gore in 2000).

En route to Madison Square, we'll see some of the spectacular architecture of the Ladies Mile Historic District. We'll finish with a lively stroll around Madison Square Park to learn about the iconic buildings there, including the Flatiron Building, Metropolitan Life Tower, and the New York Life building which occupies the site of the original building known as Madison Square Garden. The park itself has an interesting history that includes the story of a famous architect who was murdered inside one of his creations.

Tour ends at 23rd Street and 5th Avenue.

Your organizer,


Exploring Brooklyn's Sunset Park Neighborhood and Industry City

Needs a location

RSVP's begin Saturday, September 24th, at 5:00pm, 3 weeks before the event. Maximum 30 people including up to 10 spots for new members first and 2nd timers who land on the waiting list. If you are in any of these categories email me to request a spot.

The tour is free with an optional donation to your guide. Estimated walking distance is 5 miles. There is some up and down hill.

This tour covers history, culture, architecture, current lifestyle and neighborhood features including the innovative and historic Brooklyn Army Terminal and Industry City (both located within Sunset Park). Industry City has become a hub for food enthusiasts and also hosts cultural events. It features the Japan Village marketplace, a food hall, several breweries and distilleries (Sake, Ginger liqueur, cocktails), visual art and indoor and outdoor venues.

Meeting location: Is at the ferry dock for the Brooklyn Army Terminal
Restrooms: There are public restrooms near our meeting place.
To bring: Proof of full vaccination, lunch and/or snacks, water to drink, a hat for the sun.

Tour Overview

Formerly known as the “US Army Military Ocean Terminal” or the “Brooklyn Army Base,” the Brooklyn Army Terminal (BAT, pictured above) was built from 1918 to 1919 and served as the largest military supply base in the US through WWII. Today BAT is an affordable hub for modern industrial businesses, entrepreneurs, and working families in NYC and is a fully functioning industrial complex that houses over 100 businesses and 4,000+ manufacturing jobs. BAT also features a recently renovated Food Manufacturing Hub for small food manufacturing firms and space for fashion companies and garment manufacturers.

Designed by architect Cass Gilbert (The Woolworth Building, Alexander Hamilton Custom's House), the buildings themselves are a wonder to behold.

Sunset Park is a refreshing change of pace from the hustle and bustle of Manhattan and the more well-known Brooklyn neighborhoods. It also has a staggering variety almost like its own unique small city. Once home to the Canarsie Indians and then the Dutch in the 1600’s, the area was been settled by Italian, Irish, Polish and Scandinavians in the 1800’s and early 20th century. Nowadays the area has vibrant Latin American and Chinese communities. Industry City is a place of innovation where artisanal food and unique retail meets entrepreneurship.

Along our journey we’ll also see some distinctive and historic urban housing, quaint rowhouses and townhouses, expansive views from atop Sunset Park and a visit to Brooklyn’s 3rd largest Chinatown and a bit of Little Mexico. We'll try to make some time for sampling local fast food such as dumplings and street tacos.

We’ll end our adventure at Industry City where you can explore on your own, grab a bite to eat and use the restroom. Convenient to both the D and N subways at 36th Street & 4th Avenue.

Cheers from Hank[masked]

Past events (515)

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