RETURN TO TOTTENVILLE 2025

GOOGLE MAP: WALKING TOTTENVILLE 2025

It had been since 2017 since I walked extensively around Tottenville, the southernmost point in New York State (it would be the southernmost town in NYS, were it not a part of Greater New York). The older you get, the faster time flies! Perhaps I go into the following spiel every time I discuss Tottenville, but I visited it very early on, maybe age 6, when my parents were visiting someone there. We did not have a car, so what I think happened was we boarded the ferry at the 69th Street pier in Bay Ridge and traveled to St. George (the ferry was discontinued when the Verrazzano Bridge opened, but revived by NYC Ferry in a limited fashion in 2026) and then took a bus that went all the way south to Tottenville. I noticed the rutted Arthur Kill Road and its incandescent lights even at age 6. That’s really all I recall at this remove. This latest visit was in early October 2025. It was warm for the calendar at 85 degrees.

In 1972, age 15, I boarded a bus at St. George and took the same bus to Tottenville. The south end of the island was still not fully populated and in fact the bus driver asked me just before we got to Tottenville if I was traveling to the last stop: perhaps he was going to turn the bus around if there were no passengers! I noticed that in the area around Main Street, the streets still trailed off into woods south of Amboy Road. I was fascinated, yet frustrated at the same time, that the southern Staten Island streets on my Hagstrom were “paper streets” that yet existed only in the dreams of developers and city planners.

In 1977, age 20, the MTA had a bike-friendly program on weekends (that no one remembers) in which they ran buses in which the seats had been removed for Bay Ridge bicyclists who wanted to ride in Staten Island. I had a grand time roving all over the island, up and down hills. I was young and strong and must have reached Tottenville on occasion. You did, however, have to hustle back to the designated stop at the Staten Island Expressway and Fingerboard Road by 4 PM. Otherwide, you had to cycle to the ferry and return to NYC that way.

I did live and in-person Forgotten NY tours for 20 years from 1999-2019, and tried to do at least one Staten Island tour each year. The FNY Tottenville tour was in 2015. Though it poured rain, we were all younger and didn’t care, and we toured a Coptic church as well as the Billopp Conference House and wrapped up at Egger’s Ice Cream on Amboy (which has since closed). The neighborhood kidz were lively and friendly, though a bit perplexed at all the out of towners. Other tours took us to New Brighton, where we toured two beautiful dwellings and the now-closed Liedy’s Shore Inn; Kreischerville and its graveyards, mansions, ancient cemeteries and Killmeyer’s Inn. Will I return to live touring? My back will have to get better.

Before I talk about Tottenville, a bit about the St. George station, the north end of the Staten Island Railway (formerly Staten Island Rapid Transit). I discussed the line and its stops extensively, relating its history, in 2007. The line on the south side of the island to Tottenville is the last remaining of three different branches; formerly, the railroad also ran to South Beach and Arlington (Mariners Harbor).

SIRT North Beach Branch
SIRT South Beach Branch

After decades as the last repository for 1970s R44 cars, the SIRT has now fully updated to new R211S cars and as such, is the most modern rapid transit rolling stock on any NYC rapid transit line.

Unlike all other SIRT stations, the St. George station is covered by an overhead deck supporting bus runways that connect to the ferry terminal. Not only that, the RR also enters a short tunnel before finally emerging into sunshine halfway to the next stop, Tompkinsville. Station lighting is relatively new LED lamps that originally carried sodium bulbs when installed 15-20 years ago.

You’ve seen the first SIRT stop. Here’s the last, at Tottenville. The tracks abut the Arthur Kill waterway separating Staten Island from New Jersey. In spite of its remoteness Tottenville has been the terminus of the South Shore line of the Staten Island Railway since the 1860s, and three of the island’s major roads, Arthur Kill Road, Amboy Road and Hylan Boulevard, also lead here.

Though officially, New York City is the southernmost town in New York State, Tottenville, on the southern end of Staten Island, was actually the southernmost village when it was a part of Westfield Township when Staten Island was an independent county prior to 1898. The Totten family owned a large amount of property in the area in the 18th Century, and after a series of names like Unionville, Bentley Dock, and others, the village settled on a name befitting its major property holders.

Seen here is the former “Bentley Dock” ferry landing at the north end of Bentley Street. The Tottenville-Perth Amboy Ferry ran for over a century, ending operations finally in 1963; in Staten Island, only the pilings remain at the foot of Bentley Street, but in Perth Amboy the old landing shed has been retained and restored, even though resumption of service is quite unlikely. The stationhouse matches the design of other SIRT stationhouses and likely was erected in the 1930s. A decorative slip building can be seen in Perth Amboy.

A look at the Bentley dock in a 1940 tax photo, from 1940s.nyc. The ferry landing was moved permanently to the north end of Bentley Street in 1896.

A look north from Bentley Street to Arthur Kill Road. It’s one of the lengthiest roads on the island, but doesn’t approach the lengths of Hylan Boulevard or Richmond Avenue. Arthur Kill Road is approximately the same length as Amboy Road and runs from the Richmondtown Restoration to Tottenville. Within the town it was once called East Broadway, Washington Street and Fresh Kills Road for much of its length, but by 1917 or so it had become Arthur Kill Road for its full length. The name is a transliteration of old Dutch “achter kil” meaning “the other waterway,” which is what the Arthur Kill was called in contrast to the Kill Van Kull. The roadway largely parallels the waterway.

No one publicizes it much but Tottenville has a terrific collection of “painted lady” Victorian-era dwellings, some of the best north of Cape May or Mount Tabor, NJ. This is #42 Bentley in brilliant royal purple and gold at Arthur Kill Road, built in 1907 for David and Lena Williams, dealers in granite and marble monuments.

#53 Bentley Street, with its multiple gables, was built for factory foreman Seymore Case in 1910.

I admired #76 Bentley so much, I shot it from two separate angles. It’s one of the oldest examples of Greek Revival dwellings in Tottenville, and among the oldest as it was built around 1850 by oyster catcher Aaron Van Name, a prominent 19th century Tottenville family. The house was sold to ship captain William DeWaters (a logical name for a ship captain). Its present owners upkeep it lovingly. My camera is attracted to houses with small eyelet windows.

Cobblestones are uncommon in NYC (bricked roads here are made of Belgian blocks, not cobblestones) but you do find them occasionally, as in the fence at #76. Neighboring #72 has one, as well. It, too, was constructed about 1850.

#115 Bentley was constructed in 1908 for Arthur (insurance broker, banker) and Mary Yetman. The Yetmans were another prominent family in Tottenville: Civil war veteran Hubbard Yetman became a civil engineer, insurance agent, member of the NY State Assembly and staten Island superintendant of schools; Yetman Avenue bears his name.

I can picture myself on that wraparound clapboard porch at #88 Bentley, drinking iced tea. The Victorian was built for shipbuilder John Brown around 1890. Brown partnered with his father and brothers with the A.C. Brown and Sons Shipyard.

More than any other borough Staten Island’s neighborhood streets are named for prominent locals. In the 1800s, the Hopping family owned grocery stores and saw mills in the newly founded Tottenville. Hopping Avenue runs for just two blocks, but each is lengthy, between Bentley Street and Amboy Road. It’s a short way from the Arthur Kill, but private property sits between the road and the shoreline.

#12 Hopping Avenue has a dormer window and a bay and a short porch on the ground floor. And, more cobblestone fencing. If only modern residential architects would be this imaginative and meticulous. It’s a relative newcomer, built in 1921 for electrician Edward Taylor.

Bear in mind, most of the homes on Hopping Avenue are Landmarks Preservation Commission worthy, and I am only showing the ones that the camera was most attracted to. Here’s #38, with a massive dormer containing two arched windows and a shady porch with eaves supported by four massive square columns.

Patten Street is the only intersection on Hopping between Bentley and Amboy and on the corner we find this beauty at #60 with twin gables (dig that trio of tiny windows on the third floor, I’d like to occupy that room) and a bay window. Built in 1896 for train conductor William O’Connor.

South of Tottenville Shore Park, a natural wilderness area, additional homes sit on Hopping Avenue’s west side and are located near the shoreline with wide front lawns. #65 Hopping Avenue was built in 1903 for salesman Frederick Baxter. The Colonial Revival was a plan by architect Walter Cassin, who designed several homes in the Prospect Park South neighborhood in Brooklyn. Hard to tell from here, and I didn’t want to intrude on private property, but the building features massive Ionic half-columns (pilasters) on the corners. Imagine the water views.

The detailing at the Gothic Revival cottage #92 Hopping Avenue is reminiscent of the work of Alexander Jackson Davis. It was constructed in 1886 for Helen Ward, perhaps of the Ward’s Point family for whom the southernmost point in NY State is named.  

Ward’s Point is named for the Ward family, who for a time owned the historic Billopp-Conference House. After the American Revolution, what became known as the Conference House passed through many successive owners after the loyalist Billopps were forced to vacate. The building was purchased by Samuel Ward for his son Caleb Ward Senior, who divided the property into smaller parcels for his five children and his many grandchildren. A family scion, Caleb T. Ward, developed Stapleton; his mansion still stands on Ward Hill near the St. George Ferry in New Brighton.

Across the street is #91 Hopping, with multiple gables with peaks you could cut your fingers on. There’s a narrow porch with a pediment handy for getting they keys when it’s raining. The house was built in 1900 for D. Agnew Joline (another Tottenville street name) and Leonora Wartz. Joline is described as an “oyster planter” in Barnett Shepherd‘s “Tottenville: The Town the Oyster Built,” which I’m using for much of the descriptions in this page.

If you look carefully on the left, you can see the water views that go all the way to the town of Perth Amboy, NJ. The tall spire is the impressive Roman Catholic church of St. Stephen/St. John Paul II, which, as you might guess, serves a highly Polish congregation. 

Here we see the west end of Amboy Road at Ward’s Point Avenue, where it meets the Arthur Kill.  It’s one of the lengthiest routes in Staten Island, splitting off from Richmond Road in New Dorp and running through Great Kills, Annadale, Pleasant Plains and other neighborhoods to the Arthur Kill waterway in Tottenville. Interestingly, Amboy Road house numbering in New Dorp doesn’t begin at #1; rather, it continues Richmond Road’s numbering in the 2500s, with Richmond Road skipping to #3009 and continuing west from there. Though a busy route, it is mostly a two-lane road with parking, occasionally expanding to four but never becoming a behemoth as, say, Richmond Avenue does. The new house on the right is built on a relatively new street called Aviva Court.

The street name can also be found in Brooklyn and Queens. Irving Shulman’s novel The Amboy Dukes tells the story of East New York street gangs in the 1940s; Ted Nugent’s first band in the 1960s, which had the big hit “Journey to the Center of Your Mind” was named for the novel.

Staten Island is a borough whose street names have changed more than once over the centuries. In southern Staten Island the few routes that ran through the area have changed: Washington to Arden; Bridge to Richmond; Fresh Kills Road to Arthur Kill Road. Yet, Amboy Road has remained consistent since at least 1873, as on this set of maps. Also see another set from 1917.

Amboy Road is named for Perth Amboy, New Jersey, which in previous centuries was accessible by ferry from Tottenville. The city, in turn, has two names of wildly different origins: Amboy from the Lenape Indians, who called the region Ompage, and Perth after Scotsman James Dummond, 4th Earl of Perth; in the colonial era, Scottish immigrants settled in the area (across the Arthur Kill, southern Staten Island was dominated by French Protestants called Huguenots, and immigrant Belgians, called Walloons.

The wealthiest residents of Tottenville live near the waterfront, taking advantage of views of the Arthur Kill and New Jersey. This turreted palace with the large driveway and lawn is #43 Wards Point Avenue at Perth Amboy Place.

I followed Satterlee Street to Conference House Park. Located at its north end is Captain Henry Hogg Biddle’s grand mansion at 70 Satterlee, which was built on the water’s edge between 1840-1845 in a Dutch Colonial style with unusual two-story porticoes. At the time, Biddle operated the ferry between Tottenville and Perth Amboy, NJ (the ferry was in operation until 1963). Note that the front and back of the house are designed the same, with four large Doric columns. In fact the house is symmetrical, with the north and south sides the same and east and wet ends the same. The house is now owned by NYC and is part of Conference House Park. Biddle’s grove, a summer resort on the northern part of Biddle’s Farm, was established in the early 1850s. The house is now the location of the Tottenville Museum.

I had hoped to get inside to take a look around, but as my perennially poor luck would dictate, a private event was being held. Fear not, as Sergey Kadinsky had already vouchsafed passage earlier in 2025.

Tucked to the rear of the Biddle Mansion is another very old dwelling that has been preserved, the Rutan-Becket House. Fearing my back would act up, especially on steep downhills, I did not trouble it, but SILive has some exterior and interior photos and a description, thus:

(SiLive doesn’t permit you to highlight text in order to copy it, but there’s more than one way to skin a cat.)

Historic houses are almost a casual occurrence around Conference House Park. Satterlee Street goes (mostly) sidewalk-free south of Shore Road and the Biddle House driveway. I forgot to get a closeup shot of the Hannah Ward House, #96 Satterlee. Street View fills the void nicely.

The only Ward family home remaining on Ward’s Point today was built circa 1830.  This house belonged to Caleb Ward’s granddaughter, Hannah, the wife of boatman Samuel Wood.  In 1850, Wood sold the waterfront portion of his property to William H. Rutan, and later sold the house to Theodore Leven, a Swedish immigrant.  The Leven family occupied the house for nearly sixty years. [Conference House]

The Rutan family owned several properties in Tottenville during the 1800s. The Italianate #97 Satterlee, now known as “The Heathcote” and set way back from the street with a wide front yard, was built for shipbuilder James Rutan (see Rutan-Becket House above).

I mentioned cobblestone fences above and while there are no surviving cobblestone pavings in NYC, there are some cobblestone gutters, as here at the Ward House. Douglaston also has a few, and I saw some in Bay Ridge long ago.

Billopp-Conference House

A brick mansion built by  Christopher Billopp at about 1680 at the end of Hylan Boulevard, was almost a century old on September 11, 1776 when Benjamin Franklin, John Adams, and Edward Rutledge met with Admiral Lord Howe in an attempt to stave off any future hostilities. Earlier that year, the patriots had been routed in the battle of Long Island by the admiral’s younger brother William Howe. The admiral was a friend of both Colonel Christopher Billopp, a descendant of the builder, and of Franklin. He came in with an offer from George III to forgo reprisals and grant the colonists more rights than other ones in British colonies in other parts of the world had if the colonies would renounce the fight for liberty. 

But Franklin and the others stood firm and insisted upon American independence. The conference was over in three hours, with Howe coming away believing it a disaster, and the patriots knowing that a tough fight lay ahead. What became known as the Conference House passed through many successive owners after the loyalist Billopps were forced to vacate after the revolution. It was even a factory making rat poison for a time, and like so many NYC historic buildings, it fell into abandonment and disrepair. In the 1920s, though, the Conference House Association was formed, and remaining features from the building’s past were restored to what they looked like when Howe met the patriots’ delegation.

Late afternoon in October wasn’t the best time to photograph the place, but the sun-dappled look may appeal to some.

In front of the house, a vast lawn descends to the Arthur Kill, where you can walk the beach to Ward’s Point, a quiet, mostly deserted area beneath high bluffs. A look out across the water will reveal the Great Beds Lighthouse, built in 1878, about 3/4 miles out in Raritan Bay. In 2012, I joined dozens of other lighthouse enthusiasts on a boat tour featuring NY Harbor’s lighthouses—including one or two subsequently destroyed by Hurricane Sandy.

Much of Conference House Park is landmarked by the Landmarks Preservation Commission not only as a colonial-era historic district, but also as the Aakawaxung Munahanung (Island Protected from the Wind) Archaeological Site, as multiple archeological remnants of Native American occupancy in the precolonial era have been discovered here.

When I recently discussed the Almer Russell Pavilion, I promised more views of the shoreline obtainable there, and the beautiful weather didn’t disappoint.

With that, to avoid the dreaded TL/DR complaint, I’ll call a halt here, and describe the rest of my Tottenville jaunt in Part 2.

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5/9/26