Rosehill: Home to Gen. James Benedict, War of 1812 veteran, site of iconic school campus

Rosehill, the estate of Major General James Benedict (1784-1841), was built in 1835 on Broadway three blocks south of Main Street in what would become Tarrytown, N.Y. The property eventually wound up in the hands of Benedict's daughter Ann and her husband, Capt. Edward Brown Cobb. The Cobbs’ son, attorney Augustus Gardiner Cobb, sold the house and several surrounding acres at the southwest intersection of South Broadway and West Franklin Street to the village school board in 1920. The house was moved a block north to Franklin Street where it remained until it was razed, ca. 1950. The village's second Washington Irving High School -- today's Washington Irving Intermediate School at 103 South Broadway -- was built on the original Rosehill site. (Images of America, Tarrytown & Sleepy Hollow, The Historical Society Inc., Serving Tarrytown and Sleepy Hollow, 1997)

Rosehill, known to posterity as the Benedict-Cobb Estate, encompassed some 170 acres with water frontage on the Hudson River at the southwest corner of South Broadway at Franklin Street in Tarrytown, N.Y. 

The estate included 35 acres west of Broadway, and 135 farmed acres east of Broadway, north of Benedict Avenue and south of East Franklin Street, directly across from the family home.

Tarrytown's Benedict Avenue was named after the estate’s 1830 founder, Major General James Benedict (1784-1841), who knew his way around artillery and made his fortune selling felted beaver fur hats -- think Abraham Lincoln’s stovepipe model.

Benedict's 170 acres were originally part of a 262-acre estate carved out of the massive Philipsburg Manor estate by the heirs of Thomas Wildey, whose name is familiar to Tarrytown residents as Wildey Street, just south of Patriots Park off North Broadway near the Sleepy Hollow line. Wildey fought the British in the Revolutionary War and died at the Battle of White Plains on Oct. 28, 1776. Descendants of Wildey include members of families with the locally historic surnames Storm, McKeel and O’Dell.

This 1847 map of the Village of Tarrytown shows the Estate of James Benedict, known as Rosehill, which by then was in the hands of his heirs. Rosehill extended from the Hudson River (part of which is shown at bottom as Tarry-Town Bay) and extending over 35 acres in an area wider than the extant village center from Franklin Street south to near Church Street. It extending east across today's South Broadway (then known as the Albany Post Road) into an additional 135 acres of farmland. Note that the map includes the location of the Hudson River Rail Road line that wouldn't be completed until Sept. 29, 1849, two years hence. The prospective rail line lay over water as of 1847. The fare for an 1849 one-way rail ticket from lower Manhattan to Tarrytown? 35 cents. (Westchester County Archives)

The location of Benedict’s estate on the Hudson River was seemingly preordained. He was a direct descendant through his maternal grandmother of Henry Hudson, the English explorer sailing for the Dutch East India Company for whom the river is named.

Born a year after America’s victory over the British in the Revolutionary War to a founding family of Danbury, Conn., Benedict joined a hat manufacturing firm owned by members of A-list Danbury families Tweedy, White and Hoyt, rapidly rising to partner.

In 1812, he enlisted as a lieutenant in the State of New York Army National Guard, eventually rising to the rank of captain in the 11th Artillery Regiment that defended New York Harbor against incursion by the British Navy in the War of 1812. The heavily defended harbor was never attacked by the British.

Benedict returned to his hatting roots at war’s end, eventually moving to Manhattan to oversee Tweedy & Benedict’s operations there, while manufacturing remained in Connecticut.

James Benedict, ca. 1815, would rise from lieutenant to major
general during his distinguished New York Army National Guard career.

Benedict remained in the New York National Guard at war’s end, rising to the rank of major general in charge of the Guard’s 2nd Division New York artillery in 1826. He resigned his commission in 1829.

If you wonder how the hat trade was lucrative enough to fund a Hudson River Valley estate lifestyle, the 1895 book “The History of Danbury” gives us a clue in terms of the sheer scale of the business. In 1809 there were 56 hat shops in Danbury, averaging from three to five employees each. By 1812, Samuel Tweedy and James Benedict employed 30 workers at their Danbury manufacturing plant.

During the War of 1812, beaver pelts held by Britain’s fur-trading North West Company based in Montreal were no longer available to American hat makers. Pelts seized by the U.S. were auctioned in New York, with Benedict buying them at $1 per pound. He re-sold the pelts at $5 per pound.

Beaver felt hats were de rigueur for well-dressed people at the time and Tweedy & Benedict was among the first to employ a machine that revolutionized the hat-making process. Their factory was soon turning out 24,000 hats per year.

On the political front, Benedict had a deep, longstanding friendship with famed politician DeWitt Clinton and was a staunch supporter of the one-time U.S. senator, three-term New York City mayor and three-term New York governor as well as 1812 U.S. presidential runner-up to incumbent President James Madison.

DeWitt Clinton is pictured in a ca. 1823 oil-on-canvas portrait by Rembrandt Peale. The former U.S. senator, New York City mayor and three-term New York governor was the son of Revolutionary War Continental Army Major General James Clinton and nephew of six-ter New York governor George Clinton, who served as U.S. vice president during the second term of President Thomas Jefferson and first term of President James Madison. DeWitt Clinton's post-gubernatorial career as president the Erie Canal Commission was closely entangled with Major General James Benedict's tenure in the New York State legislature. (Public domain)

Clinton, nephew of George Clinton, who served as U.S. vice president under presidents Thomas Jefferson and James Madison and was a six-term governor of New York, was a driving force behind the construction of the Erie Canal.

This is a drawing of the Old State Capitol in Albany, New York. This building housed the state legislature from 1812 to 1878, including 1824 when Major General James Benedict was elected. (Originally published in "The State Government for 1879," by Charles G. Shanks, Weed, Parsons & Co., Albany N.Y., 1879. Wikimedia Commons, public domain.)

Benedict was elected to the state legislature in 1823 and began serving in Albany in January 1824 when strong opposition to Erie Canal Commission President DeWitt Clinton arose. Clinton’s opponents voted almost unanimously in both the state house and senate to remove him from his commission post. Benedict bucked the popular political mood and spoke on Clinton’s behalf.

Benedict was one of only two lawmakers to vote against Clinton’s removal and the move paid dividends. It turned out that the public supported Clinton and Benedict was rewarded for his loyalty. In the 1825 election, Benedict was the only incumbent returned to the legislature and his mentor, Clinton, who had failed to win his party's nomination for governor in 1822 despite being the incumbent, was returned to Albany for a third term as governor.

Benedict retired from politics after completing his second term in Albany and lived out his life on his Tarrytown estate, dying in 1841 at age 57. His son, Theodore Hudson Benedict, (1821-1885) had just graduated from Yale University where he was a member of the famed Skull and Bones secret society that would produce future U.S. presidents William Howard Taft, George H.W. Bush and George W. Bush.

The Benedict family mausoleum at Sleepy Hollow Cemetery is the large stone building at the rear right of this photo taken between 1910 and 1920. In the foreground just across a small lane from the Benedict mausoleum is the family plot of Washington Irving and his relatives. Irving was a longtime neighbor of the Benedict family's Rosehill estate. His estate was on the Tarrytown side of West Sunnyside Lane on the border with Irvington.The Benedict mausoleum more recently has been largely obscured by ivy covering its facade. (Detroit Publishing Co. Collection, Library of Congress)

Theodore ran for a seat in the New York State Assembly in 1850 as a member of the Whig Party and won, beating the odds in an overwhelmingly Democratic Party district and becoming the Assembly’s youngest member. Two years later he won the Whig nomination in the race for state senate and received a glowing endorsement from the New York Times, but declined to run and left politics as he battled health issues which had dominated his life since his Yale graduation.

Theodore, who never married, lived at the family's Rosehill estate with his widowed mother Deborah Coles Benedict until her death in 1870 and remained there until his own death in 1885. Theodore’s sole occupation was the running of the family estate. He listed his occupation as "farmer" in U.S. Census documents.

Theodore’s older brother, James Milton Benedict, predeceased their mother, dying in 1867. James Milton lived with his wife in Manhattan for many years, working as a partner in a tea and coffee import firm. He had a son in 1849 whom he named Theodore Hudson Benedict in honor of his younger brother.

James Milton Benedict, eldest son of Major General James Benedict, is shown in an oil-on-linen portrait, ca. 1841, by Cephas Giovanni Thompson. (New York Historical Society Museum and Library, gift of Mrs. Reid B. Cochran, 1983)

On his death in June 1885, Theodore left Rosehill to his sole surviving sibling, sister Ann Augusta Benedict Cobb, wife of shipowner Capt. Edward Brown Cobb. Cobb was the nephew of the Benedicts’ late South Broadway neighbor, Capt. Nathan Cobb, widely considered the father of Tarrytown’s public schools. 

The Cobbses also inherited much of the family's farmland to the east of Broadway.

Theodore left the vast majority of the Benedict estate on the river side of Broadway, some 26 acres, not including additional acres of property rights under the waters of the neighboring Hudson River well west past the railroad tracks and north to near the area of today's Tarrytown Metro-North rail station, to Mary Augusta (Weed) Benedict, widow of his brother James Milton Benedict.

The water rights property was later filled in and a large part of it is home today to the Village of Tarrytown-owned property that is leased by the Washington Irving Boat Club and Losee Park. The boat club property, which features the WIBC restaurant, may be redeveloped in the future, but at no time before 2023.

Mary Augusta (Weed) Benedict, wife of James Milton Benedict, is shown in an 1841 oil-on-canvas painting by Cephas Giovanni Thompson. (New York Historical Society Museum & Library, Gift of Mrs. Pierre Jay Wurts and daughter Mrs. E. Cowles Andrus)

Mary Augusta Benedict's son, James A. Benedict, was the executor of her estate and he eventually sold her land to developers.

James Milton, Theodore and Ann Augusta shared a fourth sibling, Mary Matilda Benedict, who died at age 25 in 1849.

Theodore’s estate was valued at $250,000 (about $7.2 million today, adjusted for inflation) at the time of probate on July 2, 1885.

Ann Cobb left parts of her estate to her son, Manhattan attorney Augustus Gardiner (A.G.) Cobb. 

In addition to his legal work, A.G. Cobb was an author and environmentalist and an early proponent of cremation as an alternative to burial, believing burial to be environmentally unhealthy. He would go on to sell nine acres at the southwest corner of South Broadway and  Franklin Street to the Tarrytown school district in the early 1920s. The Rosehill mansion was moved to a lot on nearby Franklin Street. The Union Free School District of the Tarrytowns built a second iteration of Washington Irving High School on the old Rosehill site in 1925.

That building and its associated athletic fields have been repurposed and renamed Washington Irving Intermediate School at 103 South Broadway.

Rosehill is commemorated today by the aptly named Rosehill Avenue which lies about four blocks east of the old mansion site in what was the estate's farmland between Neperan Road and Benedict Avenue, which honors the Benedict clan.

103 South Broadway was the location of the former Rosehill home of Major General James Benedict and the site of Washington Irving Intermediate School today. The school originally opened as the second iteration of Washington Irving High School, in the early 1920s, replacing the original high school of that name at 18 North Broadway, a short walk north on Broadway just past Main Street, which had opened in 1897. The Rosehill mansion was moved from this site to a site on nearby Franklin Street to make way for the school.

** Links to other Gilded Age stories by this author