If you’re planning a trip and looking for the best things to do in Sleepy Hollow NY, this guide breaks everything down into clean, easy-to-skim sections so you can plan your visit quickly. Sleepy Hollow is a place where history, folklore, and natural beauty all come together. Based on Washington Irving’s timeless story, this Hudson Valley village offers historic landmarks, scenic parks, and year-round attractions—with fall being its most popular season thanks to its legendary spooky charm.
Below is a streamlined, visitor-friendly list of the top places to explore.
Legendary Sites Connected to “The Legend of Sleepy Hollow”
Old Dutch Church & Burying Ground
Built in 1685, this is one of the oldest churches in New York and the heart of Irving’s classic tale. The churchyard is atmospheric and peaceful, especially in the fall. Visitors come year-round to walk the grounds and soak in the history.
Sleepy Hollow Cemetery
The final resting place of Washington Irving, Andrew Carnegie, Walter Chrysler, and members of the Rockefeller family.
You can:
- Join a guided lantern tour (highly recommended in October)
- Take a daytime guided visit
- Explore on your own for free during visiting hours
The cemetery spans 90+ acres and includes gorgeous architecture, sculptures, and ornate mausoleums.
Headless Horseman Bridge & Statue
The original wooden bridge from the story no longer exists, but you can stand at the modern bridge over the Pocantico River near the Old Dutch Church. A dramatic Headless Horseman statue nearby makes a perfect photo stop. These spots are essential for fans of the legend.
Image Source: Sleepy Hollow
Historic Homes & Estates
These landmarks showcase the architectural, artistic, and cultural heritage of the region.
Kykuit: The Rockefeller Estate
A hilltop mansion overlooking the Hudson River, Kykuit is one of the most prestigious historic homes in the U.S.
Tours run May–November and include:
- The mansion’s interior
- World-class art collections
- Outdoor gardens and terraced lawns
All tours begin at the Philipsburg Manor Visitor Center.
Philipsburg Manor
A living history site where costumed interpreters demonstrate colonial-era life and highlight the enslaved community who worked at the estate. Visitors can explore the mill, gardens, barn, and hands-on activities.
Location: 381 N Broadway, Sleepy Hollow
Washington Irving’s Sunnyside
The restored riverside home of the author who created the Headless Horseman.
Highlights include:
- Guided tours
- Beautiful gardens
- Hudson River views
- Historic artifacts and personal belongings
Location: 3 W Sunnyside Lane, Tarrytown
Lyndhurst Mansion
A stunning Gothic Revival estate in Tarrytown with sweeping river views, beautifully landscaped grounds, and intricate architectural details.
Location: 635 S Broadway, Tarrytown
Image Source: Lyndhurst Mansion
Nature & Waterfront Activities
Sleepy Hollow isn’t just about history and folklore—it also offers peaceful natural escapes and riverfront views.
Sleepy Hollow Lighthouse (Tarrytown Lighthouse)
A historic sparkplug-style lighthouse restored in 2024. While indoor tours may not always be available, you can enjoy up-close views by walking along the Westchester RiverWalk inside Kingsland Point Park.
Rockefeller State Park Preserve
A serene oasis with:
- Miles of carriage trails
- Meadows and hardwood forests
- Rockwood Hall ruins
- Scenic views of the Hudson and Mario Cuomo Bridge
This preserve is perfect for hiking, photography, or peaceful nature walks.
Scenic Hudson RiverWalk Park (Tarrytown)
Located along the waterfront, this park offers:
- Paved walking paths
- Riverfront benches
- Gardens and open lawns
- Perfect sunset views
A great place to wind down after touring.
Image Source: Scenic Hudson
Markets, Local Flavor & Dining
TaSH Farmers Market
Held on Saturdays in Patriots Park, this lively market features:
- Local produce
- Fresh bread and baked goods
- Artisanal foods
- Live music
- Craft vendors
It’s a community favorite and perfect for weekend visitors.
Local Restaurants to Try
- Bridge View Tavern – Burgers, wings, craft beer, and river views
- J.P. Doyle’s Restaurant & Public House – Classic pub menu with a village vibe
- Horsefeathers (in Tarrytown) – Cozy and perfect for fans of Irving’s legend
- Coffee Labs Roasters – Popular specialty coffee shop nearby in Tarrytown
These spots capture the local flavor and make great stops between attractions.
Frequently Asked Questions
1. What is the best time of year to visit Sleepy Hollow?
Fall—especially late September through October—is the most popular time because of Halloween events, lantern tours, and festival energy. However, spring and summer are quieter and excellent for exploring outdoor sites and historic homes without the crowds.
2. Is Sleepy Hollow walkable?
Yes, but not fully. Many sites in the downtown area and near the Old Dutch Church are walkable, while attractions like Kykuit, Sunnyside, and Rockefeller State Park require a short drive or rideshare.
3. How long should I plan to spend in Sleepy Hollow?
A full day lets you see the major highlights, but if you want to tour multiple estates, hike, and enjoy fall events, two days is ideal.
4. Can families visit Sleepy Hollow?
Absolutely. Kids enjoy Philipsburg Manor, fall festivals, pumpkin patches, and outdoor parks. Some spooky nighttime events may be better suited to older children.
Conclusion: Why Sleepy Hollow NY Should Be on Your Travel List
Whether you’re planning a fall getaway or a peaceful weekend escape, there are countless things to do in Sleepy Hollow NY for every type of traveler. The village beautifully blends folklore, history, riverfront scenery, and family-friendly attractions. From legendary sites like the Old Dutch Church to must-see estates such as Kykuit and Sunnyside, Sleepy Hollow offers a uniquely memorable experience year-round. Add its natural parks, markets, and cozy eateries, and you’ve got the perfect destination for history lovers, families, and casual explorers alike.
