A historical tour of the county is more than just visiting museums. Head off the beaten path—explore lesser-known architectural delights and have some fun, food, and drink in several of the area’s oldest establishments.
Check in at the Castle on the Hudson (400 Benedict Ave, Tarrytown 914-631-1980; castleonthehudson.com) and stay in a suite in the circa 1900 stone castle. The mansion, originally called Carrollcliffe, was built by playwright and author General Howard Carroll, Jr., a businessman and correspondent for the New York Times. Henry Kilburn, architect of many buildings in New York City including the West Park Presbyterian Church, was the designer. Visit Playland* (1 Playland Pkwy, Rye 914-813-7010; ryeplayland.org); the art-deco-themed amusement park is listed on the National Register of Historic Places and retains seven rides that predate 1930, including the Dragon Coaster. Don’t forget to order a Nathan’s Famous hot dog (or two) and fried dough between thrills.
Return to Tarrytown for drinks at the Set Back Inn (33 Main St, Tarrytown 914-631-9740; setbackinn.com), purveyor of cold beverages since 1959 and the backdrop for period-piece films such as The Good Shepherd (2006) and Mona Lisa Smile (2003).
Enjoy an early morning walk along the carriage roads and foundation ruins of William Rockefeller’s summer mansion Rockwood Hall, now part of the Rockefeller State Park Preserve (125 Phelps Way, Pleasantville 914-631-1470; nysparks.com/parks/59). One gander at the panoramic views of the Hudson River and you’ll know why he set up his homestead here. Rockwood, where Rockefeller lived from the late 1880s until his death in 1922, is set on more than 1,000 acres, and, according to the Rockefeller Archive Center, was built using stonemasons from Scotland, master wood carvers from Switzerland, gardeners from England, and horticulturists from Japan. Among the structures on the property: a three-story coach stable, a farm barn, a hennery, 17 greenhouses, and a steel bridge spanning the New York Central Railroad tracks from the estate to a two-story boathouse on the Hudson River. A siding was added to the New York Central tracks, where Rockefeller kept his private railroad car.
In Sleepy Hollow is Philipsburg Manor* (381 N Broadway 914-631-8200, weekdays/914-631-3992, weekends; hudsonvalley.org/historic-sites/philipsburg-manor), a Colonial farming, milling, and trading center once owned by the Anglo-Dutch Philipse family, rented to tenant farmers of diverse European backgrounds, and operated by a community of 23 enslaved Africans. Interpreters in period dress demonstrate daily life in 1750; guests partake in hands-on activities such as ox-grooming demonstrations and gristmill operation.
Head back south to the next village, Tarrytown, for lunch at Greek restaurant Lefteris Gyro (1 N Broadway 914-524-9687; lefterisgyro.com), located in the circa 1894 Tudor-style Washington Building, likely named for George, that dominates the northwest corner of Broadway and Main Street.
Follow lunch with a tour of Washington Irving’s Sunnyside* (3 W Sunnyside Ln, Tarrytown 914-631-8200, weekdays/914-591- 8763, weekends; hudsonvalley.org/historic-sites/washington-irvings-sunnyside), the 19th-century home of Washington Irving, author of The Legend of Sleepy Hollow. (Irving is buried in nearby Sleepy Hollow Cemetery.) A guide talks about Irving’s iconic characters Brom Bones, Ichabod Crane, the Headless Horseman, and Rip Van Winkle and why he is regarded as America’s first internationally famous author.
Visit the Village of Irvington, named after the celebrated author—even though he didn’t technically live in Irvington. Village boundaries were not as clearly delineated in the 1830s and ’40s as they are now. Sunnyside formerly was thought of as being in Dearman (as Irvington was known), until the home and surrounding land were incorporated by Tarrytown in the later 1800s. Take a driving tour of Irvington’s preserved architectural landmarks including the Lord and Burnham office and factory. Lord and Burnham moved from Syracuse to the village in 1876 and added factory buildings into the early 1900s, many of which still stand today. The firm designed conservatories for many estates and parks, including the greenhouses at Lyndhurst and at the New York Botanical Garden. Nearby stands the Cosmopolitan Building, a rare example of Neoclassical Revival-style industrial architecture in Westchester and built by John Brisben Walker in the 1890s for his magazine of the same name (no longer based in Irvington), and the Armour-Stiner (Octagon) House, topped with a Renaissance-style domed roof and cupola and decorated with Gothic, rococo, and Stick-style details. Stop for a walk around Halsey Pond and its restored ruin, a castle-like playhouse built in 1905.
Stay in the village for a waterside dinner at Chutney Masala Indian Bistro (4 West Main St, Irvington 914-591-5500; chutney masalabistro.com), located in one of the numerous Lord and Burnham buildings built between the 1870s and 1910s.
Head south to John F. Kennedy Marina Picnic & Launch in Yonkers. Sit on a bench next to the historic 1906 Yonkers Power Station, also known as the Glenwood Power Station, an early example of a large-scale electric-generating station. The New York Central & Hudson River Railroad Company built it in conjunction with the construction of the new Grand Central Terminal (completed in 1913) in order to power the newly electrified Hudson and Harlem rail lines. Admire the Palisades as fishermen ply their lines in the Hudson River and enjoy the sunset if you can.
Continue south to the National Register-listed 1871 Alexander Smith & Sons carpet mill on Nepperhan Avenue, the largest intact mill site in the Hudson Valley. The vast manufacturing complex closed in 1954 and now houses small businesses and warehouses. In its heyday in the 1920s, daily output was about 26,000 yards of carpet (about 8 million yards produced per year) by 3,500 workers. End your Saturday at Homefield Bowl (938 Saw Mill River Rd, Yonkers 914-969-5592; homefieldbowl.com), which retains an authentic atmosphere as one of the last mid-20th century alleys still operating in the county.
Back in Tarrytown, tour Lyndhurst (635 S Broadway 914-631-4481; lyndhurst.org), designed by renowned architect Alexander Jackson Davis. He was one of the most sought-after and influential pre-Civil War architects in the United States, and his designs included the circa 1835 Greek Revival-style Dutch Reformed Church in Newburgh, New York; the circa 1844 Gothic Revival-style Wadsworth building of the Wadsworth Atheneum in Hartford, Connecticut; and numerous cottages, mansions, university, and public buildings. Stroll the 67-acre estate overlooking the river and have a picnic lunch from the Tarrytown Delicatessen (350 S Broadway 914-631-9622; tarrytowndeli.com), which still has its historic mid-20th century neon sign (a rarity these days; for more on neon signs, see: nyneon.blogspot.com/2012/10/hudson-river-neon-part-1-westchester.html). A 15- to 20-minute drive north is a county architectural (and artistic) marvel: the stained-glass windows of Henri Matisse and Marc Chagall at the Union Church of Pocantico Hills (555 Bedford Rd 914-332-6659; hudsonvalley.org/node/429). The church was dedicated in 1922, a year after its cornerstone was laid. Nelson Rockefeller commissioned Matisse to design the rose window in honor of his mother, Abby Aldrich Rockefeller; the window was dedicated on Mother’s Day, 1956. Chagall designed the Good Samaritan window, dedicated in 1965, and eight nave windows (including six windows depicting Old Testament prophets), which were installed later in the 1960s.
Follow that with a leisurely walk in nearby Pocantico Lake Park and explore the ruins of the New Rochelle Water Company’s Pocantico pump station at this little-known county park.
Head north to Ossining for another driving tour and pass by the infamous Sing Sing Correctional Facility on 354 Hunter Street. Note the original 1825 stone cellblock, which stands as one of the most imposing ruins on the Hudson River.
Also in the village, a short drive north from the prison, is the early 19th-century Brandreth Pill Factory on North Water Street. The largest building at the National Register-listed site, the 1872 mill has a French Second Empire mansard roof and dormer windows. It’s glorious in late-afternoon light.
Return to Tarrytown for dinner at literary-themed Horsefeathers (94 N Broadway 914-631-6606; horsefeathersny.com), with atmosphere inspired by Washington Irving and friends, a painted wall of famous writers—Edgar Allan Poe, Mark Twain, George Orwell, and Ernest Hemingway—and shelves and shelves of books.
Your final destination—if you dare—is a two-hour lantern tour (April through November) of Sleepy Hollow Cemetery (540 N Broadway 914-631-0081; sleepyhollowcemetery.org.), the eternal home of Washington Irving, Walter Chrysler, Andrew Carnegie, and other famous and infamous people.