Sleepy Hollow
Day Plans

Make the most of your day with our curated plans, packed with Sleepy Hollow's hidden gems and unique experiences!

day 1

Explore Sleepy Hollow History

morning

:

Start your day at the Sleepy Hollow Cemetery, where you can pay respects to Washington Irving. Wander through the historic grave sites and enjoy the serene atmosphere.

afternoon

:

Visit the Old Dutch Church, an iconic site rich in history. Learn about its significance and take some time to appreciate the architecture.

evening

:

Finish with a stroll along the Tarrytown Lighthouse. The sunset views over the Hudson River are breathtaking and the perfect way to end the day.

day 2

Nature Adventures

morning

:

Hike the trails at the nearby Rockefeller State Park Preserve. The scenic views and lush landscapes are invigorating.

afternoon

:

Picnic by the lake while watching the wildlife. Enjoy your meal amidst nature for a refreshing experience.

evening

:

Return to Sleepy Hollow for dinner at a local restaurant. Try some regional specialties and unwind after a day outdoors.

day 3

Ghostly Tales and Folklore

morning

:

Visit the Sleepy Hollow Haunted House for an immersive experience. Engage with actors and explore spooky stories from the area's past.

afternoon

:

Take a guided ghost tour of Sleepy Hollow's haunted sites. Hear chilling tales that will have you captivated.

evening

:

Wrap up with a themed dinner in a restaurant that embraces the eerie ambiance. Share ghost stories with fellow diners for a fun night.

day 4

Scenic Bike Ride

morning

:

Rent a bike and ride along the Hudson River Greenway. The fresh air and gorgeous views of the river make for a perfect morning.

afternoon

:

Stop at various viewpoints for photos and enjoy lunch at a riverside café. Relish the peaceful surroundings as you dine.

evening

:

Bike back into Sleepy Hollow and explore the charming downtown area. Discover shops and grab a dessert treat to end your day sweetly.

day 5

Arts and Culture

morning

:

Start at the Sleepy Hollow Performing Arts Center for workshops or exhibitions. Engaging with local art can be inspiring.

afternoon

:

Visit the nearby Kykuit, the Rockefeller estate. Tour the grand architecture and stunning gardens.

evening

:

Attend a live performance at a local theater. Enjoy a night filled with talent and creativity.

day 6

Riverfront Relaxation

morning

:

Enjoy a peaceful morning walk by the Hudson River. The calming sound of the water and gentle breeze sets a tranquil mood.

afternoon

:

Grab lunch at a riverfront restaurant. Savor the unique flavors while taking in the scenic view of the river.

evening

:

Sit by the river as the sun sets, creating a picturesque environment. Consider bringing a book or just enjoy the ambiance.

day 7

Family Fun Day

morning

:

Start with a visit to the nearby Tarrytown Music Hall for a family-friendly show. Engage the kids in an exciting cultural experience.

afternoon

:

Visit the local playground or children's museum for interactive fun. Watch the kids explore and learn through play.

evening

:

End the day with a family dinner at a casual eatery. Share stories from the day and enjoy quality time together.

day 8

Autumn Foliage Tour

morning

:

Take a scenic drive to explore the fall foliage in the area. The vibrant colors provide a feast for the eyes.

afternoon

:

Stop at a local farm for apple picking or a pumpkin patch visit. Experience the joys of the harvest season.

evening

:

End with a cozy bonfire, roasting marshmallows. Create lasting memories by sharing stories under the stars.

day 9

Historic River Towns

morning

:

Visit the nearby village of Tarrytown first thing. Explore its quaint shops and beautiful architecture.

afternoon

:

Take a boat tour along the Hudson River to see the scenic views from the water. It’s a unique perspective to appreciate the area's beauty.

evening

:

Dine at a restaurant in Tarrytown known for its local seafood. Enjoy fresh dishes while reflecting on your day.

day 10

Castles and Mansions

morning

:

Explore Lyndhurst, a stunning Gothic Revival mansion. Tour the exquisite grounds and learn about its history.

afternoon

:

Visit the nearby Hliday Estate for a glimpse into aristocratic life. The intricate architecture and gardens are worth exploring.

evening

:

Dine at a historical restaurant nearby that embodies the local culture. Relish a meal in a unique atmosphere.

Discover Sleepy Hollow

Read more in our Sleepy Hollow 2024 Travel Guide.

Sleepy Hollow Travel Guide