The Town and Village of Ossining comprise one diverse community built on rolling hills overlooking the Hudson River. The community, originally named Sing Sing after the native American Sint Sinck tribe, was renamed Ossining in 1901 to distinguish the community from the Sing Sing Prison, after a boycott of prison-made goods hurt businesses in the town.
Still the site of Sing Sing Prison, Ossining boasts a crescent of 19th Century architectural gems on Main Street (unfortunately partially destroyed by fire) that has been a business center since right after the Revolutionary War. A stroll through the historic center of town, which includes four magnificent churches, several grand former bank buildings and the remarkable Squire House, is a travel back in time, with glimpses of the Hudson and its beautiful western banks.
Nature lovers should not miss Teatown Lake Reservation, with its miles of hiking trails, Wildflower Island, exhibitions and educational programs. Skating on the lake in winter is a favorite past time.
The Old Croton Aqueduct, the system which once provided all of New York City’s water supply, is now a beautiful and historic linear park that runs through the community, allowing hikers to traverse the entire municipality to catch views of remarkable old houses or the famed "double arch," to pause for a great meal at one of the outstanding restaurants, and to visit the Farmers' Market on summer and fall Saturday mornings.
Only in Ossining can visitors enter the Aqueduct itself, through the Weir Chamber, on one of the occasional guided tours to inspect the brick conduit which carried water to New York City.
Nearby, at the Joseph J. Caputo Community Center, is the Ossining Visitor’s Center and Heritage Area exhibit about the development and early days of the Aqueduct, and another showing the history of Sing Sing Prison, including replicas of prison cells and the electric chair.
Further exploration will provide visitors with discoveries such as Sparta Cemetery, the Jug Tavern, Maryknoll, the Brandreth Pill Factory, some splendid architectural examples of times gone by throughout the Village, and historic milestones. They may even hear memories of John Cheever, Peter Falk's childhood, Howard da Silva, a visit from Alexis de Tocqueville, and U.S. President Chester Arthur's summer home. For more information, see www.townofossining.com, www.villageofossining.org www.ossiningchamber.org
Ossining Heritage Center - Joseph G. Caputo Community Center: A well-displayed audio-visual exhibit on the Old Croton Aqueduct. Another on Sing Sing Prison gives a sense of what it is like to "be sent up the river." Free. Open 10 a.m. - 4 p.m., Monday - Saturday. 95 Broadway. (914) 941-3189(914) 941-3189.
Ossining Historical Society Museum -
The Ossining Historical Society Museum is located in the Richard Austin House, listed on the National Register since 1988. The building serves as a museum of 19th and 20th-century decorative arts, costumes, and Native American artifacts, and features exhibits on two floors. The oil painting “Hudson River North to Croton Point” by Robert Havell, engraver for James Audubon, alone is worth the trip. The Historical Society sponsors guided historical tours and lectures, and curates an archive of materials relating to the history of Ossining and the surrounding Hudson Valley area. Entrance by appointment. 196 Croton Avenue, Ossining, NY. (914) 941-0001 www.ossininghistorical.org
The Jug Tavern (Davids-Garrison House) stands at the entry to the hamlet of Sparta, the earliest settlement in Ossining. The Jug Tavern has been on the National Register of Historic Places since 1976 and is the oldest structure in the Sparta Historical and Architectural Design District. It serves as the headquarters of The Jug Tavern of Sparta, Inc., which was formed in 1986 to preserve the building, educate the public on the historic area, and provide programs such as lectures and guided walking tours. 74 Revolutionary Road at Rockledge Avenue, Ossining, NY. email@example.com www.jugtavern.org
Sparta Cemetery - An easy walk from Jug Tavern, Sparta Cemetery is ideal for browsing with its quaint headstones and opportunities for fantasizing about legends. With only a little familiarity with Ossining history one can recognize the ghosts of newspaper publishers, former slaves, Union soldiers and the legendary "Leatherman." Revolutionary Road and Route 9..
Maryknoll Center - world headquarters for the Catholic Foreign Mission Society of America since the 1920s. Almost a community in itself, with its own zip code, Maryknoll is considered the largest structure with an oriental-motif in the country. One of the building's distinctive towers, with its Chinese pagoda-style roof, has become a familiar image to millions of people throughout the world. Over the years, thousands of the Missionary Society's supporters have visited the Ossining center to see an exhibition of missionaries' memorabilia. Somerstown Road. (914) 941-7590(914) 941-7590.
Sing Sing Correctional Facility - In 1825 construction of the prison was initiated. It was considered an ideal location because local stone, or "Sing Sing marble," could be quarried and used in the building. Also, the site was close to water transportation and accessible to New York City. Plans are being made to open a Sing Sing Historic Prison Museum in a historic building on the prison grounds but outside the walls.
Teatown Lake Reservation - Named when a group of women demanded a share of a grocer's stashed tea during Revolutionary War days, Teatown Reservation is now a large nature preserve, with its own educational center. A carefully nurtured Wildflower Island is open regularly for guided tours through spring, summer and fall. Naturalists give presentations on maple-sugaring, birds of prey, reptiles, bees, honey-making and more. Many hiking trails through hilly terrain, hardwood forests, wetlands and around the lake are open daily from dawn to dusk. Indoor exhibits provide fascinating glimpses of nature collections and an excellent small store is overloaded with great souvenirs, including tea. Many events, including a pancake breakfast to sample the maple syrup, fairs, and family days are scheduled. 1600 Spring Valley Road. (914) 762-2912(914) 762-2912. www.teatown.org
Old Croton Trailway State Historic Park - Ossining is the only place where visitors may actually enter the Aqueduct, through the Weir Chamber, used to spill off waste water during floods. Tours are arranged occasionally. There is access to the Aqueduct off Main Street, at Nelson and Gerlach Parks, and a small parking area just southwest of Dominican Sisters of Hope on North Highland Avenue. When the Aqueduct crosses Beach Road, hikers may detour to the west into the Crawbuckie Nature Preserve, a 12-acre loop down to the railroad tracks. The Aqueduct is owned and managed by the New York State Office of Parks, Recreation and Historic Preservation and offers a scenic walk from northern Westchester County to New York City. The Friends of the Old Croton Aqueduct have published an award-winning map detailing the route of the trail and attractions along the way. It is available for $5.75 in Ossining from the Ossining Heritage Center, or by calling (914) 693-4117(914) 693-4117. For general trailway information, call 914-693-0529914-693-0529, www.aqueduct.org
Briarcliff-Peekskill Trailway - This 12-mile hiking trail runs from Maryknoll in Ossining to the Blue Mountain Reservation in Peekskill. There are several recreational areas along the way, and recent improvements have made it a popular destination. (914) 593-PARK.
Louis Engel Waterfront Park - The 3.5 acre park, just south of the Ossining train station, offers beautiful views of the river, Croton Point and some glimpses of Sing Sing prison. A plaque recalls Alexis de Tocqueville's visit in the 1800s. A number of festivals and concerts are held in the park and nearby during the warmer months. (914) 941-3189(914) 941-3189.
"Crossining" - The pedestrian bridge which parallels the automobile bridge over Route 9 between Ossining and Croton was whimsically named "Crossining" by Ossining's Supervisor during the opening celebration in 1999. It provides wonderful views of the brackish Croton River as it flows through marshlands to the Hudson, with a few interpretive signs posted along the way..