Tarrytown

Tarrytown, New York, is a village on the eastern bank of the Hudson River, approximately 25 miles north of Midtown Manhattan. It rests within the Tappan Zee, a broad expansion of the river named for the Tappan Indians and the Dutch word for sea. This evocative village, with its rolling hills and river views, offers a blend of historic charm and contemporary life.

Known for its connection to Washington Irving's "The Legend of Sleepy Hollow," Tarrytown and its neighboring village of Sleepy Hollow share a deep cultural and historical tapestry. Beyond the literary fame, Tarrytown offers a lively downtown with distinctive shops, diverse restaurants, and a dynamic arts and entertainment scene.

From Alipconk to Grand Estates

The area that would become Tarrytown was originally inhabited by the Weckquaesgeeks Indians, a friendly tribe related to the Wappinger Confederacy and Mohicans. Their principal settlement, Alipconk, meaning "Place of Elms," was located at the foot of Church Street. They cultivated corn, squash, beans, and tobacco, and fished the Hudson River for shad and oysters.

The first European settlers arrived in the mid-1600s, primarily Dutch farmers, fur trappers, and fishermen. Records indicate the first Dutch residence was built around 1645, though its exact location is unknown. The fertile, loamy soil was ideal for growing cereals, especially wheat, leading the area to be known as "Wheat Town" or "Terve Town," which later evolved into Tarrytown. Another theory suggests the name comes from an early settler, John Tarry. Washington Irving, however, offered a more whimsical explanation, suggesting colonial wives named it because their husbands "tarried" too long at the local tavern on market days.

In 1681, Frederick Philipse, a wealthy businessman, began acquiring land, eventually controlling 90,000 acres and becoming the largest landowner in the Tarrytown area. His Philipsburg Manor, with its main home and gristmill in what is now Sleepy Hollow, served as a central distribution point for grain. Philipse was also responsible for the construction of The Old Dutch Church of Sleepy Hollow in 1685.

During the American Revolutionary War, Tarrytown was part of the Neutral Ground, a vulnerable buffer zone between British and American forces. A pivotal moment occurred on September 23, 1780, when three local militiamen captured British spy Major John Andre, who was carrying papers detailing West Point's fortifications from Benedict Arnold. This capture is considered a major turning point in the Revolution.

The 19th century brought significant development. The New York & Hudson River Railroad, completed in 1849, connected Tarrytown to New York City and Albany, reducing steamboat traffic and fostering industrial growth. Tarrytown officially incorporated as a village in 1870. The industrial revolution also brought an influx of immigrants, particularly Irish, who worked on projects like the railroad and the first Croton Aqueduct, New York City's original water supply system. By the turn of the 20th century, Tarrytown was known for its numerous castle-mansions gracing its skyline, considered by some to be the wealthiest place of its size in the world. The village also played a role in the Underground Railroad, with the Foster Memorial AME Zion Church, founded by an escaped slave in 1860, serving as a shelter.

The opening of the Tappan Zee Bridge in 1955, and its replacement, the Governor Mario M. Cuomo Bridge, in 2017, further stimulated commercial growth and increased traffic in the area. Today, Tarrytown continues to evolve, balancing its deep historical legacy with a dynamic present.

Begin your exploration with a visit to Washington Irving's Sunnyside, the charming home of the author of "The Legend of Sleepy Hollow" and "Rip Van Winkle." Guided tours offer insights into Irving's life and the inspiration behind his works. Nearby, the Old Dutch Church of Sleepy Hollow and the Sleepy Hollow Cemetery evoke the atmospheric setting of Irving's famous tale, with lantern-lit tours available in autumn. You can also see an iron sculpture of the Headless Horseman on North Broadway.

For architectural grandeur, explore Lyndhurst Mansion, a Gothic Revival estate once owned by railroad tycoon Jay Gould. Tours showcase its period furniture, antiques, and art. Another notable estate is Kykuit, the Rockefeller Estate, open for guided tours that highlight its architecture, art, and gardens. Philipsburg Manor offers a glimpse into colonial life as a living history museum with a working gristmill.

For outdoor enthusiasts, the Old Croton Aqueduct Trail provides scenic paths for hiking and biking with views of the Hudson River. Pierson Park at RiverWalk offers riverside strolls, views of the Governor Mario M. Cuomo Bridge, and recreational facilities including a splash pad and playground. Do not miss the Captors' Monument in Patriots' Park, commemorating the capture of Major John Andre during the Revolutionary War. The Tarrytown Music Hall, a National Historic Landmark built in 1885, continues to host a variety of performances.

The best time to experience Tarrytown for warm-weather activities is from mid-June to late September, when temperatures are pleasantly warm and breezy. July is the warmest month, with an average high of 84°F, while January is the coldest, with an average low of 24°F. The clearest skies are typically in September.

October is particularly popular due to Halloween-themed events tied to "The Legend of Sleepy Hollow," including haunted hayrides, cemetery tours, and the Great Jack O'Lantern Blaze.

Tarrytown is easily accessible, located approximately 25 miles north of Midtown Manhattan. You can reach the village via the Metro-North Hudson Line, with the train station an easy walk (uphill) to downtown. If driving from New York City, your route will take you across the Governor Mario M. Cuomo Bridge (formerly the Tappan Zee Bridge). For local transportation, consider renting an e-bike or taking a taxi from the station. The village offers a range of dining options, from farm-fresh fare to international cuisine, as well as distinctive boutiques and shops. The Tarrytown Farmers Market is held every Saturday morning in Patriots Park.