7 days in Sleepy Hollow Itinerary

7 days in Sleepy Hollow Itinerary

Created using Inspirock Sleepy Hollow visit planner

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Route & dates

Sleepy Hollow
— 6 nights

Sleepy Hollow

Sleepy Hollow ©
Sleepy Hollow is a village in the town of Mount Pleasant in Westchester County, New York. Popular historic sites such as Marian Shrine and Old Dutch Church and Burying Ground are in your itinerary. You'll explore and learn at Sing Sing Prison Museum and Briarcliff Manor-Scarborough Historical Society. You'll find plenty of places to visit near Sleepy Hollow: Mianus River Gorge Preserve (in Bedford), Cranberry Lake Preserve (in White Plains) and First Presbyterian Church of Yorktown (in Yorktown Heights). There's much more to do: walk around Rockwood Hall State Park, immerse yourself in nature at Hook Mountain State Park, contemplate the long history of Philipsburg Manor, and stroll the grounds of Sleepy Hollow Cemetery.

For traveler tips, more things to do, other places to visit, and other tourist information, use the Sleepy Hollow journey builder.

If you are flying in from Canada, the closest major aiports are La Guardia Airport, John F Kennedy International Airport and Newark Liberty International Airport. In October in Sleepy Hollow, expect temperatures between 21°C during the day and 11°C at night. Cap off your sightseeing on the 29th (Thu) early enough to travel back home.

Things to do in Sleepy Hollow

Parks Historic Sites Nature

Side Trips

Yorktown Heights, Ossining, Valley Cottage, Stony Point, Croton on Hudson
Highlights from your plan
Rockwood Hall State Park ©
Rockwood Hall State Park
Kensico Cemetery ©
Kensico Cemetery
Sing Sing Prison Museum ©
Sing Sing Prison Museum