The Little Pillbox Hat Tour – Jacqueline Kennedy Onassis and the Preservation of Our Architectural Treasures: From quietly influencing the powerful people she was surrounded with, to outright personal action, JKO fought to advance an enlightened cultural agenda inspired by her storied upbringing. Join me to learn about the very important role that our most unforgettable First Lady played in defining good taste, high culture, and the importance of preserving the livability and distinctive architectural character of American cities. We will visit buildings associated with her charmed and often not-so-charmed existence, and consider her very important advocacy work in shaping and preserving New York. Allow an hour and a half for this VIRTUAL ONLINE tour, 3 hours for this tour live, on generally level sidewalks)

Long Island Tours

Down the High Line - (Former Path to Hell!):  What a meat market! Join me for a Prowl through Manhattan's gorgeous new park, where drug addicts, prostitutes and gay/transgender life flourished in the years before its magical renaissance in the early 2000s. We'll have a colorful discussion about the industrial, architectural and social history of this pulsing artery traversing sought-after neighborhoods that restored or replaced former rail yards, food markets, slaughterhouses, and dark recesses that accommodated the seamier side of life. Join our parade of peeping Toms as we peer through glass facades at area occupants who willingly reveal their lives to this public promenade. We will learn how the High Line's history still shapes its future, while becoming familiar with Hudson Yards, Chelsea, the Meatpacking District, and prominent old and new buildings nearby. Allow 2 hours for this tour on generally level sidewalks.  

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Licensed NYC Tour Guide #2054130-DC

Puritans, Immigrants and Slaves - Central Park and the Vision of a Cohesive Society:  A new way of seeing an old classic. The Erie Canal and industrial expansion propelled NYC to the economic forefront in 1800s America. People flooded in to seek opportunity. Yet, inadequate housing and sanitation bred epidemics and squalor. Old World monarchs and aristocrats and Southern plantation owners derided the Yankee and his unholy metropolis. Join us to discover how the stewards of New York development addressed these problems, while hoping to elevate American culture and unite the city's disparate classes, religions and ethnicities through the gift of a Central Park. 2 hours, generally level walks 

The Merchant Prince of the 19 Century: A.T. Stewart and the Building of Garden City Long Island:  Join me to Prowl the lovely historic streets of Garden City, a stately enclave in central Nassau County, envisioned and created by the wealthy founder of NYs first major department store. We'll learn about Alexander Turney Stewart, an Anglo-Irish immigrant who built America's leading 19c retail emporium, while simultaneously hastening the arrival of mail-order shopping and managing both venues through their explosive growth. This tour meets at the Garden City LIRR station, and includes sights such as the Garden City Hotel, the Cathedral of the Incarnation, the former St. Paul's School, gracious homes, and courtly avenues. Lunch following can be easily arranged nearby at a number of fine restaurants in town. Allow 2 hours on gently sloped and level sidewalks. 

Worship Around the Park:  "all the leaves are brown, and the sky is grey...I stopped into a church, I passed along the way..." ("California Dreamin", the Mama's and the Papa's) What better time to view architecturally noteworthy houses of worship than the colder weather. Join me to visit religious sanctuaries of architectural interest on Central Park West, focusing on religious movements that originated or proliferated in the United States. Including the West Side YMCA, the Society for Ethical Culture, the Fourth Universalist Society, and the Second Church of Christ, Scientist. Allow 2 hours on generally level sidewalks. (good for inclement as well as good weather, as much of the tour is indoors)

The Grande Hotels of (Manhattan's) Grand Army Plaza:  Terminating the remains of the opulent 5th Avenue luxury retail zone sit the still-reigning hospitality jewels of yesteryear. The surviving triumvirate of The Plaza, The Pierre and the Sherry Netherland Hotels are notable Grande Dames of hospitality . These luxurious destinations have catered to discriminating travelers and local residents wishing to wake at the doorstep of rarified purveyors of finery, connoisseur quality restaurants, and the timeless romantic elegance of Central Park. Lets explore tales behind the creation of these landmark abodes, and their relationship with the evolving character of Millionaires Row and the changing city beyond. Allow 2 hours on generally level sidewalks. (good for inclement as well as good weather, as much of the tour is indoors)

Historic Harlem, from the 1600s thru the 1920's and Beyond:  Join me for a very Picturesque Prowl through historic Harlem, once a bucolic estate setting for gracious mansions, later a hub for European immigrants, and then the destination of southern Blacks fleeing Jim Crow and migrating to the North in pursuit of jobs and rights. We will visit settings associated with all of these phases of Harlem's history, while concentrating on the emergence of the Harlem Renaissance, that wonderful period of Harlem history when the creativity of Black writers, musicians and performers became a sought after and much admired influence on American and world culture. We will walk past Sylvan Terrace, the Morris-Jumel mansion, the Triple Nickel, Trinity Church Cemetery, Hamilton Grange, Hamilton Heights, the historic City College campus, Strivers Row, and the Abyssinian Baptist Church, and see sites where well known Harlem residents lived. We will end this enlightening and pleasurable Prowl at a special pavilion to view historic WPA era murals depicting the lives of Harlem's Black residents. Allow 3 hours for this tour (can be shortened) on urban sidewalks, either level or downhill. 

(NEW BROOKLYN TOUR!) New York City - A Native American Skyline:  American Indians traded Manhattan to Europeans for trinkets, but later exchanged their monumental talents for a handsome living that took them off the reservation and to dizzying heights. Join me for this enlightening walk in the charming and rapidly changing Boerum Hill section of Brooklyn, where we will Prowl about this lovely brownstone community and discover the history of the Kahnewake Mohawks, who once had a thriving community here. They fearlessly built the towering steel structures for NY’s most notable skyscrapers and bridges of the 20th century, but their lives were forever changed when High Steel went Up In Smoke... Allow 2 hours on generally level sidewalks. 

Sea Cliff Grove - From Religious Retreat to Artsy Long Island Island Hamlet: Join me for this walk through historic Sea Cliff, where we will admire stunning vistas over Long Island Sound, charming Victorian era buildings, and shady verdant parks. We will enjoy details of village history, including Sea Cliff's role in 19th century resort travel and how the Grove was part of a national pattern of Bible study and religious education which gave America a legacy of picturesque seaside villages. Allow 2 hours on level and sloping sidewalks.

Not-Starving Artists: How The 1800s New York Art Scene Spawned the Co-op:  While socialism emerged in the 1800's European utopian dialogue, NY artists sought to make their mark on the international art scene. Our walk will illustrate how this utopianism was adapted domestically, through the genesis of co-op living arrangements, originally by and for artists. Their goal was to enhance innovation and collaboration through proximity to an extended creative community. Join Prowler to see the West 67th St. Artists Colony; a string of well designed and appointed co-op residences that to this day are peopled with creative individuals. Then off to West 57th St. to see the institutions that were originated by these dynamic individuals - Carnegie Hall, the Art Students League, and other beautiful classic studio buildings along the way. Allow 2 hours for this tour on level sidewalks. 

Decked Out in the City (Deco-Era Buildings and NY Glamour): Step off the sidewalk and back in time to the glamorous twenties. Explore the backdrop of that romantic and high living era by joining me to view magnificent period lobbies in buildings including 30 Rockefeller Plaza, the Fred F. French Building,  the Chanin Building, and the iconic Chrysler and Empire State buildings. These opulent landmarks are local place markers in the chronology of architectural form. Learn about the frenzied one-upsmanship that bred the 1920's race to build the tallest building in the world, and the colorful characters that competed in it, forever transforming the skyline of New York and creating a vivid new language of architectural style. Allow an hour and a half for this VIRTUAL ONLINE tour, or 2 hours for this live tour on generally level sidewalks. (tour can be modified in foul weather to be mostly indoors)

Art Wars! The Founding of the Met, MOMA, and the Whitney, (and What Each Will Argue Is Art):  After the Civil War, stewards of our young nation sought to develop artists with talent to rival that of Old Europe. Their goal was to elevate the level of refinement of the average American, and prove that we could be preoccupied with more than the almighty Buck! On this pleasant Museum Mile trek, we will discover how the keepers of our first cultural collections defined art and decided what would or would not hang within their walls, in the process competing with each other and the highbrow institutions of overseas. This is an outdoor tour focusing on museum architecture as a reflection of their founders and the collections inside. Tour includes viewing and discussion of the exterior of the National Academy of Design and Whitney Museum uptown, as well as the landmarked Metropolitan and Guggenheim Museum facades. Allow an hour and a half for this VIRTUAL ONLINE tour, or 2 hours for this live stroll on generally level sidewalks.

Altman’s! Bergdorf! Saks! - A History of Elite Shopping on Fifth Avenue: Join me for this colorful tour of 5th Avenue retail palaces, endearing themselves to the Ladies of Fashion while displacing them from what was initially New York’s most exclusive and expensive residential real estate. We will enjoy the architectural details of these and other sumptuous Fifth Avenue buildings while learning about the quirkiness, genius, and motivation that fueled the ambitions of their creators and propelled New York to become fashion capital of the world.  Allow 3 hours for this tour, in and outdoors on generally level sidewalks.

Inspired Insanity! – Nikola Tesla in New York:  Prowl the local haunts of the mad genius who brought us the Induction Motor, Current Wars, power distribution, a deluge of patents, and a fantastic deserted monument meant to generate wireless power, graphic images, sounds, data and maybe even a focused DeathRay into the aether! Backed and then deserted by the Robber Barons of the last century, Tesla’s musings, inventions and rantings predicted and gave form to our modern technological era. Join me to walk in the local New York footsteps of this eccentric and colorful resident, who left a charged impression on Our Fair City.  Allow an hour and a half for this VIRTUAL ONLINE tour, 3 hours for the live tour on generally level sidewalks. 

Castles In the Air - Glamorous Hudson Yards and its Historical Underpinnings:  Join me to Prowl through North America's largest private mixed use real estate development - Hudson Yards. This massive new commercial-residential realty project is just beginning to transform the far west side of Manhattan. We will trace its evolution from industrial and then dilapidated property, into a glamorous, transformative pedestrian culmination for the recently developed High Line and for the evolving 34th Street corridor. All this, while leaving intact its foundations in the railroads and tunnels that brought and continue to bring the masses into New York.
Highlights include a walk through the upscale new retail area anchored by Neiman Marcus, and through the public plaza area, including The Shed performance and exhibition venue, and a short section of the High Line. The tour will culminate with a visit inside the magnificent public sculpture currently known as The Vessel. This is a 2 hour tour on mostly level terrain, with the exception of the Vessel which is accessed by stair or elevator, and the indoor shopping area, accessed by escalator.

​​"So, What Brings You Here?" - Immigration in New York, From Its Beginnings until Now:  Join ProwlerNYC for a pleasant ride on the Staten Island Ferry, to view Lady Liberty, Ellis Island, and our impressive metropolis from the water, while learning about government policy toward immigrants since the founding of New Amsterdam. This interesting discussion will surprise you with little known facts about how the Federal government has relied upon science and social policy to control and reform immigration and the American population. This is a non-partisan discussion of immigration policy and how it has evolved in response to changes in prevailing values of our nation. We will meet at Castle Clinton in lower Manhattan, proceed to the ferry, ride it to and from Staten Island non stop while viewing vistas of interest on both sides of the ship, and return to the ferry port in lower Manhattan. Allow 2 hours on generally  level sidewalks, includes stairs or ramps. 

East Meets West - 15 Central Park West and the New Uptown Aristocracy:  The Upper East and West sides have been staring each other down since before the last century. In the 1800s, the East River and the Hudson River were active ports lined with the often unsavory industries that catered to sailors and merchants. As a result, the truly wealthy avoided the waterfront and built mansions in Greenwich Village, eventually migrating uptown along Fifth Avenue. On the other side of the park at Central Park West, the first apartment buildings and co-ops emerged; a middle class answer and perhaps challenge to the lifestyles of those across the way. Join us for a walk and discussion on how the two major avenues flanking the park competed, clashed, and copied each other, from then until now. Allow 2 hours on generally level sidewalks. 

A Phoenix Rises from Ashes: the New York Central Railroad and the Making of Midtown: In 1902, the dominance of the Vanderbilt-controlled NY Central Railroad was threatened by a ban on their steam powered locomotives in Manhattan, as well as by the rival Pennsylvania Railroad tunneling under the Hudson River and arriving on Manhattan's west side. Join ProwlerNYC to learn how the NY Central responded to these challenges,  creating a precedent in development that continues to revolutionize New York City real estate to this day. Content covers the growth of midtown and the development of the skyscraper, with stylistic examples from its earliest incarnations, to today's 'Supertall' structures on or near Park Avenue. Tour begins in front of the Pershing Square Cafe,  90 West 42nd St. across from Grand Central Terminal, and ends at architect Rafael Vignoly's 432 Park. Allow 2 hours for this tour on generally level sidewalks. 

A Magnificent Stroll to the Fire Island Lighthouse (or, "The Power Broker" in Less Than A Thousand Pages) :  Join me for a stunning walk at Robert Moses State Park,  while we experience the legacy of the "Master Builder" who shaped Long Island and the New York metropolitan area. The subject of numerous books including a famous lengthy biopic by Robert Caro, Robert Moses transformed both the city and state of New York by creating the Long Island State Park system, New York metro and suburban area parks and parkways, expressways, bridges, tunnels, playgrounds, housing projects, upstate power generating stations, the Lincoln Center complex, and two World's Fairs. A controversial figure, he is both lauded and loathed. What do you think of his legacy? We'll decide while prowling about in some of the most beautiful oceanside woodland terrain that the world has to offer, reaching the historic and picturesque Fire Island Lighthouse and then returning to the State Park kiosk. Beach walking is not part of this tour unless requested by participants. This easy stroll is on level groomed boardwalk paths with spectacular views. (Adventurous walkers can continue walking along the beach to the Fire Island town of Kismet, where there are several lively restaurants and a General Store.) No boat rides necessary, the Park is accessed by bridge. This is a great walk in any season. Allow 2 hours on generally level boardwalk.

Historic Oyster Bay LI: Including the Culper Spy Ring, Teddy Roosevelt, Robert Moses, and Billy Joel!:  Join ProwlerNYC for a beautiful and entertaining Prowl through the charming streets of Oyster Bay Village. We will explore landmarked buildings revealing Revolutionary War history, the tenure of resident Governor and then President Theodore Roosevelt, Depression-era politics and art, and the ever evolving community of live and ghostly Oyster Bay residents of the past, up to the present day. Our stroll will take us past charming colonial era buildings and cottages, Queen Anne and gothic-styled churches, leafy streets and charming secret gardens, and the spectacular Oyster Bay waterfront. Allow 2 hours for this stroll on mostly level sidewalks.

Philistines at the Hedgerow - Prowling Historic Southampton: Join Prowler for a stroll through the spectacular estate section of Southampton. We will view historic homes, landscapes, social clubs and houses of worship, and enjoy the distinctive architectural character of these noteworthy structures and surrounding gardens. Tour departs from lovely Southampton Village. Fab shopping! Allow 2 hours on mostly level sidewalks or lawns.


Tours are on level or gently sloped ground unless otherwise noted. ideal for ages 14 through adulthood. Sturdy shoes, a water bottle, and weather-appropriate clothing are recommended. All tours are handicapped accessible.