Springside: Broadway estate once hosted Irving School for Boys, now iconic Sleepy Hollow High

This mid-1860s mansion, shown in an undated early 20th century photo,was built by chocolate magnate William Lawrence Wallace on his 10-acre Springside estate in what is now the Village of Sleepy Hollow, N.Y. It was home to 13 Wallace children born to three different wives. After 1904 it became one of three main buildings on the Irving School for Boys campus. The Irving School, named for co-founder Washington Irving, was established in 1836 as the Irving Institute. The name was changed in 1891 (Photo courtesy Westchester County Historical Society, special thanks to Patrick Raftery, WCHS Assistant Director and Librarian)

Antebellum Southerner William Lawrence Wallace made his fortune in the North as a Manhattan confectioner, constructing an iconic facade on Main Street of his adopted Tarrytown hometown and raising 13 children in a magnificent mansion on his Springside estate that stood into the mid-1950s.

Springside enjoyed Hudson River vistas, a 10-acre tract on the east side of North Broadway just inside today’s Village of Sleepy Hollow. It would become home to one of the nation’s top private boarding schools, The Irving School for Boys, in 1904 and it's  where Sleepy Hollow High School opened in 1957.

This 1868 north-south oriented map shows the 10-acre Springside estate established by Manhattan confectioner William Lawrence Wallace on what is today the Sleepy Hollow side of its Andre Brook border with Tarrytown. Springside featured a gatehouse near its southern gate on Broadway with a stable for horses and carriages at its southeastern intersection with the Croton aqueduct. The main mansion is just above the L in W.L.Wallace above Springside.The estate continues east beyond the aqueduct. The site would become home to the Irving School for Boys in 1904 and Sleepy Hollow High School in 1957. Springside surrounded two of the three sides of the First Reformed Church and parsonage property (center top) off North Broadway that is the Korean Church of Westchester today. The property on the immediate north side of the First Reformed Church would become the Larchlawn estate of John Myers Furman after 1891 when he bought the Irving Institute on nearby Pocantico Street. Furman would buy Springside in 1904 and make it the campus of the renamed Irving School which it remained until 1955. Furman turned the old Springside gatehouse into the Irving School's infirmary soon after buying the estate and bought the nearby church's parsonage in 1929 for school use as well. (Frederick W. Beers, 1868, David Rumsey Historical Map Collection)

Wallace manufactured and retailed his own chocolate in Manhattan and built his mansion before 1868 at 210 North Broadway diagonally across from Patriots Park on what is today's Tarrytown/Sleepy Hollow border. He was living in the general area no later than 1853.

The Richmond, Va., native might best be remembered today for the $60,000 ($2 million today) he spent to build the Tarrytown Music Hall at 13 Main Street, Tarrytown – a block west of Broadway – which opened in December 1885 and still operates at a high level today. When he first built it, it was called Wallace’s Opera House. It is the oldest operating theater in Westchester County and has been a staple on the Tarrytown scene for the better part of 140 years.

William L. Wallace built the Tarrytown Music Hall which opened in December 1885 at 13 Main Street, Tarrytown for $60,000 (inflation-adjusted $2 million in 2023). It remains open today with some 180 performance days scheduled per year. (Google Maps photo, May 2023)

Wallace’s first confectioner's store was at 29 Cortlandt Street in Manhattan, a couple of blocks east of today’s One World Trade Center, the former Freedom Tower. When Wallace’s chocolate empire was at its peak, the Trade Center site had been home to the Washington Market since 1813. The market generated massive foot traffic and sales for Wallace.

Later, Wallace and Company opened a chocolate manufacturing operation at 1149 Broadway, a four-story building that still stands, in February 1885. The company’s mantra was “Wallace and Company: Manufacturers of fine chocolates, chocolate bon bons and French confectionery by steam process.” The ground floor at 1149 Broadway – between 26th and 27th streets – was Wallace’s retail shop. The factory was in the top floors. Today the ground floor remains a retail shop, as of late 2023 the Fellow Barber NoMad Flatiron salon.

William Lawrence Wallace, c. 1885

Wallace married three times and was widowed twice. He had four children with his first wife, 28-year-old Caroline Jannett Hooff of Washington, D.C. She was his first cousin – his mother’s brother’s daughter – and he eloped with her against his father’s wishes. Wallace’s father disowned him as a result . Caroline died at 37 on May 4, 1860 in Manhattan, nine days after giving birth to the couple's fourth child, son Carolyn Stuart.

Carolyn – yes, a boy – was preceded by sisters Eliza Hooff and Isabella (who would die at age four), and brother William Halsey Wallace. The name Carolyn apparently confused census takers; in the 1860 U.S. Census, the three-month-old infant’s identity is handwritten, incorrectly, as “Calvin, Son.”

Wallace next wed Caroline Goldsborough Gardner, 34, in 1862. Her father Col. John L. Gardner had just retired from an artillery command for the Union Army, capping a 48-year career that had begun during the War of 1812 and ended with seven months service in the Civil War.

This is an aerial 1930s photo of the Irving School for Boys campus on the Sleepy Hollow border with Tarrytown. To the far right, center, is the Margaret Howard Home for Aged Seamstresses, formerly the Edward Walker Harden mansion, Broad Oaks. That building is now the Public Schools of the Tarrytowns Administration Building. Immediately to its left is the Irving School and its campus buildings with an athletic field on the heights at rear. At left, front, of the campus is the First Reformed Church, today’s Korean Church of Westchester with its parsonage, later bought by the Irving School at its rear. Straight across (right) from church is a small white building at the North Broadway entrance to the campus that was the gatehouse and at the time of this photo the school infirmary. The main white building at center left of the campus is the former Springside estate mansion. (Robert Yarnall Richie photo c. 1932-34, DeGolyer Library Digital Collections, Southern Methodist University)

This Caroline died in 1873 after having five children with Wallace including daughters Kate Gardner and Mary Isabel, and three sons, Gardner, who died at seven months old, Benjamin Lawrence and Charles Goldsborough. Mary Isabel was born just a few months before her mother’s death.

Wallace married for a third time, c. 1875. His wife, Emilie Frances Savage, may have been as young as 18 at the time and at any event was several months younger than Wallace’s eldest child, daughter Eliza. Emilie was 27 years younger than Wallace and the couple had four children, sons Robert Newby and Maury Savage and daughters Emilie Laurette and Jessie Hunter.

Wallace's will at his death in November 1890 saw the late businessman name Eliza and Emilie two of three co-executors of his estate -- a male neighbor was the third -- and noted that Eliza had faithfully and diligently helped raise many of her half-siblings. None of Wallace’s daughters married during his lifetime, except Kate, who eloped against her father’s orders and was disowned by Wallace, just as Wallace's own father had once disowned him.

Kate challenged her father’s will, causing an uproar among scandal mongers of the day. Reports at the time said Wallace had forbidden any of his daughters to marry and all obeyed those orders except Kate. Wallace reportedly spurned her future husband’s formal appeals for Kate's hand on at least two occasions, finally prompting the couple to elope.

The grave monument of William L. Wallace at Sleepy Hollow Cemetery, Section 30, 540 North Broadway, Sleepy Hollow, N.Y., reads: “I Know that my Redeemer Liveth … Wm. L Wallace … Born Feb. 22, 1824 Fell Asleep Nov. 8, 1890 … Mark the Perfect Man and Behold the Upright for the End of that Man is Peace” (Screen capture, findagrave.com/memorial/69495388/william-l-wallace)

Kate ran off with Harry Hamilton Wood in 1889, just over a year before her father’s death from pneumonia. Kate, 24, and Harry, 23, wed in Jersey City, New Jersey and made their home in Harry’s hometown of Ossining, not far from Kate’s father’s estate. She eventually reached a $15,000 settlement with her family to end her litigation over the will. Brother Carolyn Stuart was left a nominal $50 in the will because his father said in the will he’d advanced him extensive funds while he was living. The son also sued and reached a $15,000 settlement with the estate. The rest of Wallace’s $1 million estate – the equivalent of $34 million in 2023 – was supposed to be divided equally among surviving family members after the North Broadway estate was sold.

Eliza never did marry. She ended up as a boarder in a house in Mount Vernon, N.Y. The Woodses’ ill-fated union ended in divorce after three children and a little more than a decade. Kate ended up living out her days in a rented apartment in Manhattan and Harry wound up a field hand for an Indiana farmer, dying of a fractured skull suffered in a farm accident in 1929.

In life, Wallace, an Episcopalian, served as Senior Warden at St. Mark’s Memorial Church – known colloquially at its inception as Washington Irving Memorial Church. It became Immaculate Conception Roman Catholic Church in 1957 and today is St. John Paul II Maronite Catholic Church at Immaculate Conception. It remains at 199 North Broadway, Sleepy Hollow, near Wallace’s old estate.

After Wallace’s death in 1890, the chocolate factory moved to Brooklyn where it continued to operate through the first half of the 20th century.

This postcard, c. 1917, shows the Irving School for Boys campus on the old Springside estate of William Wallace with its three main buildings. The Springside mansion (left) came with the purchase of the estate and was used by the school. The building at center is believed to be the first building constructed on the property after the move and consisted of the main body, which was new construction, as well as the left and right wings which were moved from the school’s old campus on Pocantico Street off Beekman Avenue. The final building, which housed the school’s gymnasium, among other things, was the South Building, right, which was built in 1912. (Postcard courtesy Westchester County Historical Society)

Wallace's Springside has been a centerpiece of Sleepy Hollow since he first developed it and remains so today.

The Irving Institute, “An English and Classical Boarding School for Young Gentlemen,” was founded in 1836 by author and diplomat Washington Irving, writer, journalist and editor William Cullen Bryant of the New York Evening Post newspaper (The New York Post today), Scarborough estate owner and U.S. Navy Vice Admiral Alexander Slidell Mackenzie, and Daniel Webster (Congressman, orator, U.S. Secretary of State under three presidents), among others. It began its first term in 1837 in a building on the site of today’s Van Tassell Apartments, 95 Beekman Avenue, Sleepy Hollow, and remained there until after the Civil War when it moved less than two blocks away to the northeast corner of Pocantico Street at its intersection with Howard Street when the institute was purchased by a new headmaster, David S. Rowe.

This engraving c. 1836-46 shows the original Irving Institute building at the northwest corner of Beekman Avenue at Pocantico Street before its move up Pocantico to its southeast intersection with Howard Street after the Civil War. Note the stable at the left rear of the original school building. The site is home to Van Tassell Apartments today. (Image courtesy Westchester County Historical Society. Thanks to Tracy Van Akin for information leading to the correct pre-1846 dating of this image.)

The old Beekman Avenue building remained the site of schools for some six more decades. It was F.J. Jackson Military Academy until about 1900 and from then to 1926 it was St. Teresa’s Parochial School, affiliated with St. Teresa of Avila Catholic Church. The church remains at 130 Beekman Avenue today.

Rowe bequeathed the Irving Institute to son-in-law Frank Armagnac in the early 1880s. Armagnac sold the school to John Myers Furman in 1891. Furman purchased the former 10-acre Wallace estate from Wallace’s heirs in 1904 and moved the newly renamed Irving School for Boys to that location where it would remain until closing its doors in 1955.

The Irving School for Boys’ proprietor
and headmaster Rev. Dr. John Myers Furman
 is shown in a 1925 photo. (Irving School
yearbook Sketch Book 1925)

At the time Furman bought the school it was teetering on the edge of failure. Enrollment, despite being opened to day students from the area, had declined to just three boarding students and 11 day students.

A bright future lay ahead under Furman’s leadership, but a look back at the past gives an idea of what the Irving Institute honoring co-founder and namesake Washington Irving was like at its founding 54 years earlier.

According to a prospectus for the school published in the Aug. 24, 1836 edition of The New York Evening Post newspaper, it was noted for its healthy, country location while still being accessible, “being visited morning and afternoon by steamship from New York.” The railroad would not come to Tarrytown until 1849.”

The campus of the Irving School for Boys is shown in a c. 1914 postcard after the school’s move to the campus – formerly the Springside estate – in 1904 by owner and headmaster, Episcopal Rev. Dr. John Myers Furman. The original William L. Wallace Springside mansion is at left center with mansard roof. Furman added the other two main school buildings right center and right by 1912 after buying the 10-acre estate from Wallace’s heirs. The old gatehouse from Springside, bottom left, was turned into the school's infirmary. Furman changed the college preparatory boarding school’s name from Irving Institute when he bought it in 1891 The school was founded in 1837 and the property and buildings sold to the Public Schools of the Tarrytowns in 1955. Since September 1957 the campus has been the site of Sleepy Hollow High School, 210 North Broadway, Sleepy Hollow, N.Y. At far left, front, is the former First Reformed Church, which is now the Korean Church of Westchester. The Reformed Church's parsonage, not pictured, was at the back of the church and was purchased by Furman in 1929 for school use, likely as a dormitory. (Image courtesy The Historical Society, Inc., Serving Sleepy Hollow & Tarrytown)

The co-headmasters – referred to as Principals at the time – of the new school were brothers William P. Lyon and Charles H. Lyon. William Lyon would assume complete control when his brother left for a school in Greenwich Village in 1842.

The prospectus continues: “A commodious brick edifice has been erected expressly for (the school). The grounds are ample, offering abundant opportunity for sports in the open air, and quite retired from the village (today’s Tarrytown, the village wasn’t incorporated until 1870). The site being elevated, the prospect is extensive and delightful, commanding a view of the river from New York (City) to the (Hudson) Highlands (of Orange and Putnam counties).

Arguably the Irving School of Boys most famous alumni – Major League Baseball Hall of Fame members Eddie “Cocky” Collins (left) and Tom Yawkey (right) – are pictured in this c. 1934 photo at Fenway Park in Boston, with Yawkey’s wife, Elise. Collins (1887-1951), from Millerton in Dutchess County, N.Y., played second base on the World Series champion Philadelphia Athletics in 1910, 1911 and 1913 and Chicago White Sox in 1917. He was on the team but did not appear in the Athletics’ World Series wins in 1929 and 1930. Yawkey (1903-76) was raised in Manhattan by his uncle, Detroit Tigers’ owner Bill Yawkey, and inherited his uncle’s fortune in 1919 while at Irving School. He bought the Boston Red Sox in 1933 after turning 30 and receiving his complete inheritance. Collins, a friend of Yawkey’s because of their Irving alumni ties, laid much of the groundwork for the deal and was named vice president and general manager by Yawkey. He held those posts until 1947. Yawkey owned the Sox until he died. (Photo courtesy Boston Public Library, Leslie Jones Collection c. 1934)

“The teachers and pupils reside in the family of one of the Principals, eat at the same table, sleep under the same roof, and constitute, in all respects, one of the family and the discipline is entirely of the parental kind. …

“… The moral welfare of youth being always a consideration of the first importances, it is an object of solicitude with the Principals (headmasters William P. Lyon and Charles H. Lyon) to bring their pupils under the salutary influence of moral and religious principles, without interfering at all with the tenets of particular denominations. Each pupil must be provided with a Bible and will be required to attend at family prayers morning and evening, and public worship on the Sabbath in one of the churches (of which there are four) in the village, such place as may be agreeable to the wishes of parents or guardian.

Miss Metcalf’s School for Girls occupied this house, shown in an undated Russell & Lawrie Druggists postcard, likely c. 1900, which still stands at 15 College Avenue, Sleepy Hollow, directly behind the former St. Mark's Memorial Episcopal Church, today’s St. John Paul II Maronite Catholic Church at the Immaculate Conception at College and Broadway, across the street from the Irving School. The Irving School purchased the Miss Metcalf house in 1919 for use as a dormitory for its boarding students. On the bottom right of the photo, note what appears to be a sort of sidewalk extension into the street that includes a block for people to step down from a horse or carriage and to its left a hitching post for horses. (Postcard courtesy Westchester County Historical Society)

“The system of education pursued in this institution is designed to prepare the pupil for the active duties of life, or for a course of professional or collegiate studies, and, if desired, for any degree of collegiate advancement.

“The studies (offered) are: Orthography, Reading, English Grammar, Rhetoric, Geography, Astronomy, History, Composition and Elocution; Arithmetic, Algebra, Mensuration, Geometry, Trigonometry, Surveying, Penmanship and Bookkeeping; Chemistry, Natural Philosophy (today’s physics), Botany, Geology, Mineralogy, Natural History; Latin, Greek, Hebrew, French and Spanish languages; Greek and Roman Antiquities; Ancient Geography and Mythology.

“… The year is divided into two sessions – one commencing on the 1st of May, and the other on the 1st of November, each succeeded by a vacation of three weeks …

“… Terms, $100 per session ($3,412 today) … This will include tuition, board, washing mending, fuel, light, etc., and also the use of the library. There will be no extra charges. Pupils … can remain in the family of the Principal during the vacations, if desired – subject to charge for board.”

Sleepy Hollow Middle School and High School, pictured after a $66 million project completed in 2008 that added this three-story building fronting the old campus, now occupy the high ground east of North Broadway that once served as the William L. Wallace estate Springside and later housed the Irving School for Boys campus. The site originally housed just Sleepy Hollow High School. (Photo by Sheila Thompson, London, CC by 2.0, Wikimedia Commons)

The Irving School closed its doors after its commencement exercises on June 5, 1955. Walter Gray Mattern Jr., 28, J.M. Furman's grandson, had been headmaster of the school for six years and announced the closing. He said the school had been chartered as a nonprofit educational corporation by the New York State Board of Regents and would move to the 250-acre Troutbeck estate in the Dutchess County town of Amenia, N.Y. intending to open in the summer of 1956. There is no indication that it ever did.

Mattern himself cut his ties with The Irving School immediately. He became headmaster at Wilbraham Academy in Wilbraham, Mass., for the fall semester of 1955 and remained there until 1971. He died in 1999.

This artist's rendering of Sleepy Hollow High School and its campus is shown shortly after its opening on a postcard c. 1958.

The Irving School campus was sold to the Public Schools of the Tarrytowns for $285,000 funded to a large extent by a $300,000 donation from John D. Rockefeller Jr. of the nearby Kykuit estate. Demolition began soon after the final commencement and the Sleepy Hollow High School opened for the start of the 1957-58 school year.

Clockwise, from top left, are 1938 Irving School for Boys faculty department heads Frank Harvey Harman (math), Merritt Powell Durkee (junior class, head coach), James Melius Barriskill (latin, drama), George Werntz Jr. (English) and Leonard Morrell Hunting (science). (Photo courtesy Tracy Van Akin)

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