On State Street at Main Street, on the right when traveling south on State Street.
Bella Vista and the Secor Road Stone Wall
On this site once stood this Italianate-style residence built circa 1862 and owned by Azariah and Mary Baxter Carpenter. They called it "Bella Vista" because of its beautiful and sweeping . . . — — Map (db m193245) HM
On Albany Post Road (U.S. 9) 0.8 miles north of Emwilton Place, on the right when traveling north.
'Careswell,' built in 1835 in the Greek Revival style, was once home to Gen. Aaron Ward (1790-1867), a native of Sing Sing and alumnus of the local Mount Pleasant Academy. He fought in the War of 1812, served in the U.S. House of . . . — — Map (db m193213) HM
On Pleasantville Road at Brookville Avenue, on the right when traveling west on Pleasantville Road.
Officers.
Charles C. Hyatt Capt. 12th U.S.I. •
Franklin J. Davis 1st Lieut. 11th N.Y.C. •
William Mattocks 2nd Lieut. Co F. 17th N.Y.I. •
Charles S. Livingston Masters Mate U.S.N. •
Leonard Cronk Sergt. Co I. 6th N.Y.H. Art. •
Elijah . . . — — Map (db m193269) WM
On Ellis Place at South Highland Avenue (U.S. 9), on the left when traveling east on Ellis Place.
Ellis Place and the Little Shop Tea Room
Ellis Place originated as the Ellis Estate, which in 1851 was sold to local investors who divided the 13-acre property into 66 lots. Ellis Place, lined with gracious Victorian homes, is . . . — — Map (db m193217) HM
On Eastern Avenue at South Highland Avenue (U.S. 9), on the right when traveling east on Eastern Avenue.
George Rohr's Saloon and Boarding House
In the mid-nineteenth century Ossining was bustling industrial, commercial and transportation center; and this large, French Second Empire style building placed in the busiest intersection . . . — — Map (db m193221) HM
On Maple Place at South Highland Avenue (U.S. 9), on the right when traveling east on Maple Place.
Highland Cottage
(Squire House – Mud House)
Highland Cottage was built in 1872 in the High Victorian Gothic style by H.J. Baker, an Ossining resident and industrialist, who employed specially trained workers from . . . — — Map (db m193193) HM
On Main Street south of Central Avenue, on the right when traveling south.
Lower Main Street Ossining
From the mid-1800s to the early 1900s Downtown Ossining was one of the most important merchant and shipping towns on the Hudson River, supplying Westchester County and New York City with produce and . . . — — Map (db m193229) HM
On South Highland Avenue (U.S. 9) just north of Maple Place, on the right when traveling north.
Ossining High School
Ossining High School, built in 1929 was designed by famed architect James Gamble Rogers. The Tower, rising three stories above the main building, represented the highest point in the village when built, and was . . . — — Map (db m193216) HM
On Main Street at Church Street, on the right when traveling west on Main Street.
Welcome to Historic Ossining
The Village of Ossining can trace its beginnings to 1685, when the Sint Sinck Indians sold their land along the east side of the Hudson River to Frederick Philipse, who established a large manor. After . . . — — Map (db m193182) HM
On St. Paul's Place just east of State Street, on the right when traveling east.
The Calvary Baptist Church and Annex
The Calvary Baptist Church and Annex, formerly St. Paul's Episcopal Church were built during Ossining's 19th century industrial boom. As the population grew, the local Episcopalians organized in . . . — — Map (db m193246) HM
On Croton Avenue (New York State Route 133) north of Elizabeth Street, on the left when traveling north.
The Carnegie Library
The Ossining Public Library began in the 1880s as a collection of 700 books located in the School Superintendent's Office at the Park School; it was housed at various locations over the next few years. Looking . . . — — Map (db m193224) HM
On Albany Post Road (U.S. 9) at Main Street, on the right when traveling south on Albany Post Road.
The Crescent
Main Street is known as the Crescent, so named for its half-moon curve as it descends from Route 9. The upper portion of Main Street historically fronted on Pleasant Square at its intersection with the Albany Post . . . — — Map (db m193186) HM
On South Highland Avenue (U.S. 9) at Church Street, on the right when traveling south on South Highland Avenue.
The Cynthard Building
The Union Hotel, built in 1800, once stood on this site. It was for many years the official Village “stage house” for the York and Albany Turnpike Stag Company. Many important persons stopped at the hotel, . . . — — Map (db m193191) HM
Near Broadway just west of Leonard Street, on the left when traveling west. Reported damaged.
The Double Arch
In 1833, with New Yorkers seeking pure water, the City's Water Commissioners decided that the Croton River would provide the best source of drinking water. Construction of the aqueduct arch was done by Andrew Young . . . — — Map (db m193227) HM
On Albany Post Road (U.S. 9) at Church Street, on the right when traveling south on Albany Post Road.
The First Baptist Church
The First Baptist Church was officially organized on November 12, 1790, with 33 members under the leadership of Elijah Hunter. Hunter had served as a spy under the command of John Jay during the . . . — — Map (db m193188) HM
On Croton Avenue (New York State Route 133) near North Highland Avenue (U.S. 9), on the left when traveling north.
The First National Bank and Trust Co.
The First National Bank and Trust Co., which was designed and constructed in the Art Deco and Neo-Classical styles by the Hoggson Brothers firm, opened on May 20, 1930. At the top of the façade . . . — — Map (db m193225) HM
On Maple Place at South Highland Avenue (U.S. 9), on the left when traveling west on Maple Place.
The First Presbyterian Church
The First Presbyterian Church of Ossining, designed in High Victorian Gothic style by architect Isaac Gale Perry, was completed in 1870 at a cost of $95,000. This church is actually the third to bear . . . — — Map (db m193192) HM
On State Street at Academy Place, on the right when traveling south on State Street.
The James Robinson House
With its prominent columns and hipped roof, the James Robinson house is an outstanding example of Greek Revival architecture, popular around the time of the Civil War. It was owned by the same family as the . . . — — Map (db m193250) HM
On State Street just south of St. Paul's Place, on the left when traveling south.
The Mount Pleasant Academy Library
This is the only surviving building of the Mount Pleasant Academy, a major educational institution for over a century. Opened in 1814, the Academy offered a range of subjects to students of both . . . — — Map (db m193248) HM
On Main Street at Church Street, on the right when traveling west on Main Street.
The Old Croton Aqueduct is a brick and stone conduit, built between 1837 and 1842, to carry water from the Croton River into New York City. Since it is a gravity flow system, a gradual decline had to be maintained throughout the Aqueduct's . . . — — Map (db m193184) HM
On Main Street at Church Street, on the right when traveling west on Main Street.
The Old Croton Aqueduct Promenade
The pathway over the Croton Aqueduct arch is known as the Promenade. During the 19th and early 20th centuries, the Promenade was a popular place to stroll. Romantic and picturesque places to . . . — — Map (db m237839) HM
On South Highland Avenue (U.S. 9) at Main Street, on the right when traveling south on South Highland Avenue.
The Ossining Bank for Savings
When the Sing Sing Bank for Savings was founded in 1854 with $3,900 on deposit, it was located across Pleasant Square from its current location. The bank's first president was Benjamin Brandreth, . . . — — Map (db m193187) HM
On Main Street at Central Avenue, on the right when traveling south on Main Street.
The Ossining National Bank
The Ossining National Bank, remodeled in 1906 in the Renaissance Revival style, was inspired by the famous library of St. Mark's in Venice, Italy. Included among these elements are the red, hipped Spanish . . . — — Map (db m193228) HM
On State Street at Broad Avenue, on the right when traveling south on State Street.
The Smith-Robinson House
Hudson River marble, technically a dolomitic limestone, quarried at Sing Sing Prison was used as a popular 19th century building material. This house is one of four remaining Sing Sing marble buildings in the . . . — — Map (db m193252) HM
On Emwilton Place just east of South Highland Avenue (U.S. 9), on the left when traveling east.
The United Methodist Church
By 1875, the Methodist congregation had outgrown their church on Spring Street and decided to build a new edifice. They acquired a site on Highland Avenue and began construction in 1877; however, their . . . — — Map (db m193215) HM
On Croton Avenue (New York State Route 133) just north of South Highland Avenue (U.S. 9), on the right when traveling north.
The Village of Ossining Municipal Building
The Ossining Municipal Building was built in the Beaux-Arts style in 1915 to provide space for the Village's government including the Police Department and the courts. It was designed by . . . — — Map (db m193222) HM
On South Highland Avenue (U.S. 9) at Main Street, on the right when traveling north on South Highland Avenue.
Trinity Episcopal Church is a Gothic Revival limestone building built in 1891 and designed by Robert W. Gibson. It is laid out in the form of a cross along an East-West axis and has several stained-glass windows made by the Louis . . . — — Map (db m193220) HM
On South Highland Avenue (Albany Post Road) (U.S. 9) at Church Street, on the left when traveling north on South Highland Avenue (Albany Post Road).
Union Hotel stood on this corner about 1800 to 1890. Owned by Enoch Crosby Jr., later by Simeon M. Tompkins. Stage stop N.Y.–Albany & Somers. — — Map (db m34686) HM
On Broadway at North Highland Avenue (U.S. 9), on the right when traveling west on Broadway.
Village of Ossining Community Center - Weskoria Hotel
The Joseph G. Caputo Community Center is home to the Ossining Heritage Area exhibit, showcasing the history of the first chartered municipality in Westchester County. The . . . — — Map (db m193226) HM