Skip to main content

Sleepy Hollow, NY Road Trips

Plan drives from Sleepy Hollow, NY with practical route pages for distance, drive time, fuel cost, road character, and places to stop along the way.

village in New York, United States

Photo: Wikimedia Commons

Trip Routes

4

Longest Drive

37 mi

Brooklyn, NY

Quickest Drive

29m

New Rochelle, NY

Plan Around Sleepy Hollow, NY

Trips from Sleepy Hollow, NY

Sleepy Hollow, NY by the Numbers

Recent demographic snapshot from the US Census Bureau's American Community Survey.

Population

10,592

Median Income

$101,652

Median Home Value

$756,700

Median Age

39.6

Source: US Census Bureau ACS 5-year (public domain). See our methodology for details.

Notable People from Sleepy Hollow, NY

A sampling of people born in Sleepy Hollow, NY.

Eric Paschall

Eric Paschall

1996

American basketball player

Sam Coffey

Sam Coffey

1998

American soccer player

Tony Taylor

Tony Taylor

1990

American basketball player

Keith Hamilton Cobb

1962

American actor

Kate Ebli

1958–2011

American politician (1958-2011)

Jeffrey A. Meyer

Jeffrey A. Meyer

1963–2025

United States District Judge

Landmarks & Historic Sites

Attractions and heritage-registered places located in Sleepy Hollow, NY.

Sleepy Hollow Cemetery

Sleepy Hollow Cemetery

cemetery in Sleepy Hollow, New York

National Register of Historic Places listed place
Philipse Manor

Philipse Manor

railway station in Sleepy Hollow, the United States of America

National Register of Historic Places listed place
Philipsburg Manor House

Philipsburg Manor House

historic house in New York, United States

New York State Register of Historic Places listed place National Historic Landmark

City data from Wikidata (Q1025065), available under CC0. Photos from Wikimedia Commons under their respective licenses. See our methodology for details.

Traveler Guide to Sleepy Hollow, NY

Sleepy Hollow is a village in Westchester County in the state of New York. It was one of the settings for Washington Irving's short story "The Legend of Sleepy Hollow".

Founded as an agricultural center in Dutch New Netherland by Frederick Philipse. Philipse switched allegiance to England when the British evicted the Dutch, but his heirs were less astute in their political affiliations: 3rd generation Philipses continued allegiance to England during the American Revolution and were forced to forfeit their vast land holdings. After the war, the small hamlet around the Philipse's mill was renamed Beekmantown after a prominent patriot family. By 1874 the hamlet had grown into a village and incorporated as North Tarrytown. In 1996 residents of the village voted to change its name from North Tarrytown to Sleepy Hollow to distinguish it from the adjacent village of Tarrytown. Sleepy Hollow shares a zip code and a school system with Tarrytown, but the two villages are separate municipalities. Washington Irving's short story "The Legend of Sleepy Hollow" is set here and in Tarrytown. In the story, "Sleepy Hollow" is the valley of the Pocantico River, now largely occupied by Sleepy Hollow Cemetery and Rockefeller State Park Preserve. Sleepy Hollow Chamber of Commerce provides tourist information and descriptions of seasonal events on its web site and in its storefront window: 1 Neperan Rd, Tarrytown, +1 914 631-1705.

The main attraction is Sleepy Hollow's association with Washington Irving's short story "The Legend of Sleepy Hollow", so visit the old churchyard where the Headless Horseman purportedly rests. If you look hard you might find the headstone of Catriena Ecker Van Tessel whose anglicized name, Katrina Van Tassel, appears in Irving's story. 1 Old Dutch Church and Burying Ground, 430 N Broadway. The church has been in continuous use since around 1690, except for a few years during the American Revolution. Free guided tours of the burying ground from Memorial Day Weekend through the end of October, Sundays at 2PM. Self-guided tour book Tales of the Old Dutch Burying Ground is sold at the Philipsburg Manor museum shop. This is the spot where Ichabod Crane sought sanctuary from the Headless Horseman. If you happen to be here after dark, keep in mind that ".the Headless Horseman. it was said, tethered his horse nightly among the graves in the churchyard." Park inside adjacent Sleepy Hollow Cemetery. 2 Sleepy Hollow Cemetery, 540 N Broadway, ☏ +1 914 631-0081. Gates open M-F 8AM-4:30PM, Sa Su 8:30AM-4:30PM. Pay a visit to Washington Irving, Andrew Carnegie, Walter Chrysler, William Rockefeller, and Elizabeth Arden in their final abodes. The style of architecture ranges from Victorian rural at the cemetery's south end to grand neo-classical mausoleums at the north end. Free maps are available in literature boxes at the cemetery office and at the cemetery's south gate. 3 Philipsburg Manor Upper Mills, 381 N Broadway, ☏ +1 914 631-3992.

Follow Ichabod Crane's route. Fans of Washington Irving's "The Legend of Sleepy Hollow" can follow the route of Ichabod Crane from the center of adjacent Tarrytown north into Sleepy Hollow. But don't expect to find the "Western Woods" or anything else from the 1999 movie Sleepy Hollow. Tim Burton's production is only loosely based on Irving's story and was filmed largely in Hertfordshire, England. The original bridge is long gone, but there's a rustic bridge inside Sleepy Hollow Cemetery. Sleepy Hollow Cemetery walking tours. Day and evening guided tours introduce some of the famous and infamous residents of Sleepy Hollow Cemetery, including Washington Irving, author of "The Legend of Sleepy Hollow," industrialists Andrew Carnegie and William Rockefeller, and others. Old Croton Aqueduct. Go hiking or bicycling on the aqueduct's trailway. The original water supply to New York City is now a walking trail that runs from Croton-on-Hudson in the north to Yonkers in the south. Notably, the trail passes through the Lyndhurst estate in the south end of Tarrytown, and very near Washington Irving's Sunnyside. Over the 180 years since it was built, portions have disappeared from the downtown areas of several river towns, including Sleepy Hollow (part of Sleepy Hollow High School is built on top of the aqueduct, forcing a detour behind the school). Hike, horseback ride, fish, or go birding. At Rockefeller State Park Preserve. Equestrians can park horse trailers at the park's main entrance (in case you wish to make your own horseback ride through Sleepy Hollow).

1 Hollywood North Pizza, 109 Beekman Ave, ☏ +1 914-631-7406, [email protected]. Su–Th 10AM–10PM, F Sa 10AM–11PM. (updated Apr 2021) 2 Ambar Restaurant, 60 Clinton St, ☏ +1 914-631-6393. M–Th 10:30AM–9PM, F Sa 10:30AM–9:30PM, Su 10:30AM–8PM. A hole-in-the wall Dominican-American that offers good food at reasonable prices. 10AM-7PM daily, closed Tuesdays. Formerly the Cuban-American Corona's Lunch. 3 Chuchok Thai, 404 Old Broadway, ☏ +1 914-909-5390, [email protected]. F-Su 4–9PM, Tu W 4–9PM. Excellent authentic Thai food, the best in the area by far. As of Dec 2021, it is open for pick-up only due to pandemic. A small, family operation, it’s so popular you should call in your order well in advance. They also accept orders by email before 3PM. (updated Dec 2021) 4 Blue Hill at Stone Barns, 630 Bedford Rd, ☏ +1 914 366-9600. Su W Th 5-10PM, F Sa 5-11PM. Blue Hill is an upscale restaurant located at the Stone Barns Center for Food and Agriculture, a model farm adjacent to Rockefeller State Park Preserve. Appropriate attire required. Prix fixe three-course dinner $65, prix fixe four-course dinner $75.

1 J. P. Doyle's, 48 Beekman Ave, ☏ +1 914-631-3015. M 5–11PM, Tu–Su 11AM–10PM. Irish pub in Sleepy Hollow’s business district. Dinner daily 5-11PM, lunch F-Su 11:30AM-3PM. (updated Apr 2021) 2 Bridge View Tavern, 226 Beekman Ave, ☏ +1 914-332-0078, [email protected]. M 3–9PM, Tu–Su noon–9PM. 18 varieties of beer on tap.

There are no places to sleep in the town, but nearby Tarrytown has some options.

1 Westchester County Airport (HPN IATA), 240 Airport Rd, White Plains, ☏ +1 914 995-4860 (airlines). The closest airport, about a 20-minute drive. Rental cars are available. 2 Stewart International Airport (SWF IATA), 1180 First St, New Windsor, ☏ +1 845 564-2100. Another alternative to the congestion of the 3 major airports. Allegiant Air, American Eagle, and JetBlue operate flights from Florida and Philadelphia. (updated Mar 2021) Newark Liberty International Airport (EWR IATA), Newark, New Jersey, John F. Kennedy International Airport (JFK IATA), and LaGuardia Airport: The three major international airports in the New York City area offer service to just about anywhere. Westchester-based taxi and livery cars offer regular service to and from the three internationals from most areas of the county. New York City yellow cabs will take to you Westchester in a pinch, but the fares can be exorbitant. Ask if your hotel offers shuttle service. Sleepy Hollow is easily accessible from the northeastern United States and southeastern Canada via interstate highways such as the New England and New Jersey Turnpikes (I-95) and the New York State Thruway system. The I-87 portion of the Thruway connecting Albany and New York City crosses the Hudson River in adjacent Tarrytown on the Tappan Zee bridge as does I-287, which connects with I-95 to the east.

If arriving by train from New York City and planning only a day trip within the central business district, you can get about on foot or by local taxi. NY Waterway tours have their own bus transportation between destinations. If you stay in local hotels or motels, a car becomes something of a necessity. Broadway (aka Route 9) is the main north to south route through the village.

Dial 911 from any telephone for emergency police, medical, and fire services.

Travel tips adapted from Sleepy Hollow on Wikivoyage, licensed CC BY-SA 4.0. Content summarized; visit the source for the full article. See our methodology for how we use it.

How Much Time Do You Have?

Pick your one-way drive time and see where you can go from Sleepy Hollow, NY.

No routes in this time range.

destinations from Sleepy Hollow, NY.

Nearby Hubs

Other cities within driving distance of Sleepy Hollow, NY that also have route pages.

Escape Planner

Where to go from Sleepy Hollow, NY?

Curated day trips, weekend getaways, and overnight routes — grouped by how much time you have and the kind of trip you want.

Drives from Sleepy Hollow, NY in your inbox

Monthly note with new routes, weekend drive ideas, and seasonal picks for NY. No spam, unsubscribe anytime.

Browse more NY road trips or choose a route from Sleepy Hollow, NY above.