Castle Gallery at The College of New RochelleCastle Gallery at The College of New Rochelle

The History of Leland Castle

Simeon Leland, the “business prince” who built New Rochelle’s Castle, began life in 1816 as the eldest son of a Vermont innkeeper. He and his four brothers served their first apprenticeship at their father’s inn, the Green Mountain Coffee House in Landgrove, Vermont, and went on to achieve considerable fame and fortune as hotelkeepers. In 1837, young Simeon moved to the city of New York and soon took over the management of the well-known and fashionable Clinton Hotel, with the help of two brothers, Charles and Warren. During his years at the Clinton, Simeon married a New Yorker, Eleanor Moore.

Simeon Leland

Simeon Leland

In 1851, the Leland brothers — now the firm of Simeon Leland & Company — took a lease on the new six-story Metropolitan Hotel in New York. The brothers commissioned Charles to travel throughout Europe to study the various hotel systems there. The luxury of continental hotels undoubtedly impressed Charles, because, on his return, the Lelands effected important changes in American hotel-keeping. The Metropolitan soon became celebrated for its excellent French cuisine and sumptuous appointments.

During the nineteenth century, the American hotel became a large financial enterprise, in sharp contrast to the small family businesses of earlier times. Wise entrepreneurs capitalized on the need for large, well-staffed and capably managed hotels. The Lelands were partially responsible for initiating and improving this minor revolution in American hotel operation. The sons of the Leland brothers continued the family trade into the early years of this century, and built a nation-wide reputation.

In 1848, Simeon Leland purchased 40 acres of farmland in New Rochelle, as the future site of his weekend and summer home. Actual construction of “Castle View” did not begin until 1855, when Leland’s success as proprietor of the Metropolitan enabled him to afford the enormous cost of building and decorating his mansion.

Leland apparently was also interested in building up New Rochelle’s resort trade, for in 1861 he purchased David’s Island in Echo Bay, intending to build a hotel there. However, the Civil War intervened, and he leased the island to the Union Army for use as a military hospital. After the war the Lelands sold David’s Island to the government; later it became Fort Slocum.

Contemporary articles about Leland picture him not only as a person with a shrewd eye for opportunity, but also as one who genuinely enjoyed entertaining on a lavish scale, Unlike the medieval fortresses from which his home took inspiration, Leland’s Castle never isolated its inhabitants from the world around it. From the time Simeon Leland first occupied his mansion to the present, the lion-studded black walnut doors have been opened to welcome thousands of visitors from all over the world.

The Castle was Leland’s vacation home until 1872, when his lease on the Metropolitan Hotel expired. At that time the hotel’s new owner gave its lease to “Boss” William A. Tweed. Leland then retired permanently to New Rochelle. He died shortly thereafter on August 3, 1872.

When Simeon Leland died, he was deep in debt. His Castle had reportedly cost $35,000 to erect and was at one time valued at over $100,000. Sometime before his death he was forced to mortgage the entire property, and he died before the mortgage could be paid. Leland supposedly had requested that his wife use his $35,000 insurance policy to settle the mortgage, but for some reason she failed to do so, and the mortgage was foreclosed. Although the Castle was then owned by the Manhattan Life Insurance Company, Mrs. Leland continued to live there until March 1880.

At that time the Queens County Hunt Club, composed of members of several Westchester clubs, leased Leland Castle for their various functions. The New York Times announcement of the lease states that Messrs. Oliver Iselin, Delancey Kane — both residents of Davenport Neck, New Rochelle — and F.G. Griswold had rented the building for two years with the plan of turning it into an inn similar to English roadway inns, at which Hunt Club guests could spend the night. Thus, Leland Castle was known as the Castle Inn from 1880 to 1882.

Delancey Kane, a wealthy member of New York society and brother-in-law of Iselin, was a pioneer in the short-lived sport of public coaching in the late 1870s. Members of his New York Coaching Club (primarily members also of New York’s “Four Hundred”) took paying customers and guests to various hotels, clubs, and estates in Westchester, Long Island, and New Jersey. With his famous coach, the “Tally-Ho,” Kane sponsored regular runs from the Brunswick Hotel in New York to the Huguenot Hotel in New Rochelle and later to the “Castle Inn.” Kane and Iselin converted the Castle’s sweeping front lawn to a polo field, and the surrounding woods were soon populated by fox hunters.

The members of the Queens County Hunt club did not renew their lease on the Castle when it expired in March 1882. Several weeks later, on the night of March 30, the old public school building of Trinity School burned to the ground; immediately the school board met and voted to lease the vacant Castle for a temporary school. Thus, for two years, public school classes were held in the Castle.

In 1884, Adrian Iselin, Jr., the son of Oliver Iselin, bought Leland Castle, its 40 acres, and an adjacent farm with the purpose of developing the land into a residential park. During the next five years, the Castle was presumably used as a boarding house. Then, from 1889 to 1892, the building was rented by the New Rochelle Collegiate Institute, a boarding school for young boys.

Leland Castle in the 1890s

Leland Castle in the 1890s

Sometime after the tenancy of the New Rochelle Collegiate Institute, Leland Castle lost the crow-stepped gable over the entrance and the arched wooden porte-cochere. Subsequent changes are difficult to trace because of the absence of photographs or written descriptions during this period. The greenhouse and three wooden verandas were demolished. Possibly it was at this time that the rear section of the Castle grounds, now known as the Cloister Garden, was excavated; the Leslie engravings show a veranda in this area, adjacent to the Dining Room and Drawing Room. The 40 acres of the original estate were diminished to 2 1/2, while Iselin’s new Residence Park, one of America’s early suburban “developments,” occupied the gardens and woods of Leland’s former estate.

Adrian Iselin, Jr., a shrewd businessman, did not try to sell Leland Castle until most of the plots of the Residence Park were sold. Possibly he realized that an individual buyer would not want such a large mansion on so small a piece of property. Rather, an institution such as a school seemed a more likely client. Thus, after serving as a boys’ boarding school, Leland Castle became a girls’ boarding school in 1896, when a Miss Morse of Boston rented the building for her academy.

During that year, Mother Irene Gill, the Ursuline prioress and principal of St. Teresa’s Convent and Normal School on Henry Street in New York, visited New Rochelle and called on the Iselins with the hope of renting or buying the Castle. Anxious for larger quarters and the cleaner air of the suburbs, Mother Irene had been directed to New Rochelle as an ideal place for a young ladies’ seminary. But since the building had already been leased to Miss Morse, Mother Irene was obliged to begin her school in a house which she purchased on Locust Avenue in New Rochelle. On January 13, 1897, a fire broke out in a chimney of the Castle, causing extensive smoke and water damage to the building’s roof, plaster, murals, and woodwork. Uninsured against such disaster, Miss Morse broke her lease and closed the school. When an agent of the Iselins notified Mother Irene that the Castle was available, she agreed to buy it if the Iselins would repair the smoke and fire damage. This was done immediately by the architectural firm of Peter Doern of New Rochelle. During the summer the nuns moved into Leland Castle, and in September 1897, the Ursuline Seminary was opened.

The new Seminary prospered, and two years after its opening, the Ursulines had need of a larger chapel. This was built on the site of the original greenhouse as an extension of the Drawing Room; the windows, tracery, and stone were all made to match the original building. But even this addition was not adequate for long. To answer the need for more classrooms, a larger chapel, and more sleeping quarters for the growing student body and Ursuline community, in 1902 a large wing was built onto the north side of the Castle adjoining the former billiard room and picture gallery. Here too, the extension followed the Gothic style of the original. In this expanded building, Mother Irene’s newest venture, the College of Saint Angela, began to educate its first students.

In the years that the Ursuline Nuns have occupied Leland Castle, few major architectural changes have been made to the original building. On August 14, 1926, the wooden parapet of the rear north tower was destroyed by lightning; subsequently, an elevator was installed in the tower to replace the burned-out staircase. During the middle decades of the twentieth century, the poor condition of the wood construction over the bay windows necessitated their replacement with galvanized iron copies.

Time has dealt less kindly with the park and gardens. Leland’s rustic summer houses rotted away long ago, and most of the outdoor statuary was sold by Iselin when he broke up the estate in the 1880s. Vandals have removed the remaining cast-iron vases which survived the Iselin sale.

Approaching the Castle today, one no longer sees the avenue of elms that once lined West Castle Place. Instead, what meets the eye is a pleasing assemblage of college buildings which take their basic inspiration from the Gothic Castle in their midst, but which also exemplify all the architectural changes of the twentieth century. However, despite the architectural and technological advances exemplified by the newer college buildings, Leland Castle holds its own. This picturesque example of American Gothic embodies artistic and human values its more modern neighbors often fail to achieve. Here we sense an intrinsic dignity, a visible association with the past, and an opportunity for humane living in rooms that offer ample air, light, and space — in short, a dwelling that provides, not only for man’s physical need for shelter but also for his spiritual need for repose amid beauty.

Portions of this piece have been excerpted from an essay on Leland Castle by Sr. Martha Counihan, O.S.U., ‘67.


As a man whose fame rested upon his hotels’ reputations for good living and superb comfort, Simeon Leland, not surprisingly, built for himself a home of comparable qualities. He called upon the architect, W.T. Beers, and the artists, Younglin, Dorego, Delemano, and Harvest to build him an “English castellated Gothic edifice.”

Leland Castle tower

Leland Castle tower

In his choice of the Gothic style for his castle, Simeon Leland made a selection that was neither new nor unusual for the time or location. The search for a viable and evocative past led many Americans to a rediscovery of the English Gothic period through their reading of popular “Gothic” novels, their Christian religion, and their common British heritage.

Gothic castles like Leland’s were to mid-nineteenth century Americans what Greek-columned mansions had been to the previous generation. Both revival styles sprang from a common root, romanticism, which had replaced the rational, ordered ideals of the Age of Enlightenment.

The vicinity of New Rochelle boasts a number of houses in the Gothic style designed or renovated by Alexander Jackson Davis, among them Bolton’s Priory in Pelham, Whitby in Rye, Overcliff (now Wildcliff) in New Rochelle, and Lyndhurst in Tarrytown. William Beers, Leland’s architect, must have been familiar with these designs of the master of American Gothic. His work reflects Davis’ art in its use of asymmetry, of the “picturesque,” of such decorative elements as towers, bay windows, and stained glass. The assurance of the master, however, is largely lacking in Beers, the novice. Nonetheless, “Castle View” won the approbation of many and was no doubt a source of great pride and satisfaction to Simeon Leland.


Space will not permit us to describe or analyze in detail the Castle’s architecture and decoration. We will leave the description of its original beauties to a contemporary of Leland’s, Frank Leslie, whose Illustrated Weekly of October 21, 1865 devoted a full column of rapturous praise to “The Leland Palace.”

The house is of greyish stone, of the granite order, some of which was quarried at Tarrytown and some in the neighborhood of New Rochelle … It contains 60 rooms, the first floor ceilings being 16 feet high, the second floor 14 feet, every room of which is frescoed in the highest style of art…, while the woodwork is of solid black walnut, as are the stairs and all the household belongings. The grand staircase, leading from the main hall, has, directly off from its first landing the billiard-room and picture-gallery; in the latter of which is a choice collection of works of art …

From the windows, which look out upon the Sound, … five lighthouses can be seen, and a most splendid sweep over Long Island Sound and all the adjoining country. From this fact the name of “Castle View” has been appropriately given the Leland mansion. The principal rooms have been designated according to their artistical fittings, as the Gold Room, the Blue Room, the Pink Room, the Tent Room, etc., while each of its gorgeous belongings so vies with the other, that it is next to an impossibility to select one as the most beautiful … Accordingly we find rosewood and high polished walnut vieing with ormolu and gold in every apartment; china and plate, hobnobbing with velvet carpets and tapestry hangings, and beautiful caryatides and statues …

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