Sleepy Hollow & Tarrytown Day Trip — 38 Minutes from Grand Central
Tarrytown and Sleepy Hollow sit adjacent to each other on the eastern bank of the Hudson in Westchester County, 38 minutes from Grand Central by Metro-North. Washington Irving invented the Headless Horseman legend here in 1820. The Rockefeller family built their country estate Kykuit on the hill above Pocantico Hills. For World Cup visitors looking for the most effortless escape from the city, this is the answer.
Kykuit, the Rockefeller Estate
Kykuit (KY-cut, Dutch for "lookout") was the Rockefeller family home for four generations, completed in 1913 for John D. Rockefeller Sr. Nelson Rockefeller transformed the grounds into one of the finest outdoor sculpture collections in the country — works by Picasso, Calder, Moore, and Brancusi are placed throughout formal gardens overlooking the Hudson and the distant Manhattan skyline. Tours depart from Philipsburg Manor in Sleepy Hollow. Advance reservation at hudsonvalley.org is essential — summer tours sell out weeks ahead.
Philipsburg Manor & Sleepy Hollow Cemetery
Philipsburg Manor on the Pocantico River is a restored 17th-century Dutch colonial manor with a working grist mill. The Old Dutch Church next door, built in 1685, is one of the oldest standing churches in New York State and the cemetery where the Headless Horseman scene was set. Washington Irving is buried in the adjacent Sleepy Hollow Cemetery.
Lyndhurst Mansion
Lyndhurst is a National Trust Historic Site on the southern edge of Tarrytown — a 67-acre Gothic Revival estate overlooking the Hudson, designed by Alexander Jackson Davis in 1838 and enlarged by railroad magnate Jay Gould in 1880. The rose garden peaks in June.
Getting There
Metro-North Hudson Line from Grand Central Terminal to Tarrytown in 38 minutes. Trains run every 20 to 30 minutes on weekdays, hourly on weekends. Round-trip fare approximately $22. No car necessary for the main sites.
🚗 Need a rental car for this trip?
Cars book fast in World Cup summer — compare rates and reserve early.
Where to Stay
| Hotel | Tier | Why Book It |
|---|---|---|
| Castle Hotel & Spa Tarrytown | Luxury | Actual 1897 Norman castle on a hilltop above the Hudson, full spa, panoramic river views — 38 min from Grand Central |
| Tarrytown House Estate | Upscale | Two 19th-century mansions on 26 Hudson River acres, outdoor pool, tennis, walkable to Tarrytown village |
| Windrose on Hudson | Boutique | Estate hotel near Sleepy Hollow, sweeping Hudson Valley views, firelit courtyards |
| Sleepy Hollow Hotel (Dolce by Wyndham) | Mid-Range | Indoor pool, free parking, adjacent to Lyndhurst Mansion, close to all the main sites |
| Courtyard by Marriott Tarrytown | Mid-Range | Heated indoor pool, Starbucks on site, 2.5 miles from Sleepy Hollow, reliable and affordable |
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