Sleepy Hollow, New York, is more than just a setting from Washington Irving’s classic tale The Legend of Sleepy Hollow. This charming Hudson Valley village is packed with history, folklore, scenic views, and activities that appeal to travelers year-round. Whether you come for the Headless Horseman legend, the stunning riverfront, or the historic landmarks, you’ll find plenty of unforgettable experiences. If you’re planning a trip, here’s a complete guide to the best things to do in Sleepy Hollow NY.
1. Visit the Sleepy Hollow Cemetery
The Sleepy Hollow Cemetery is one of the most iconic landmarks in the village. Established in 1849, it stretches over 90 acres and is the final resting place of famous figures like Washington Irving, Andrew Carnegie, and Elizabeth Arden.
Walking tours here bring the past to life with fascinating stories about the cemetery’s residents, Gothic architecture, and of course, the legend of the Headless Horseman. Fall is the most atmospheric time to visit, when lantern tours illuminate the grounds after dark. Exploring this cemetery is a must on the list of things to do in Sleepy Hollow NY if you love history mixed with a touch of mystery.
2. Explore Philipsburg Manor
Step back into the 18th century at Philipsburg Manor, a living history museum that transports visitors to colonial times. Once a working farm and mill, the site recreates daily life in the 1700s with costumed interpreters, demonstrations, and hands-on activities.
Here, you can tour the water-powered gristmill, wander through the gardens, and learn about the people who lived and worked on the manor, including enslaved individuals whose stories are preserved. Visiting Philipsburg Manor is one of the most educational and eye-opening things to do in Sleepy Hollow NY.
3. Experience the Headless Horseman Festival Spirit
Sleepy Hollow comes alive every October with Halloween-themed festivities. From haunted hayrides to elaborate decorations, the entire village embraces its spooky reputation.
The Horseman’s Hollow, held at Philipsburg Manor, transforms the site into a terrifying haunted trail featuring ghouls, ghosts, and of course, the Headless Horseman. For a family-friendly option, check out the Great Jack O’Lantern Blaze at nearby Van Cortlandt Manor, where thousands of hand-carved pumpkins glow in artistic displays.
If you’re planning a fall trip, you’ll discover that seasonal celebrations are some of the most exciting things to do in Sleepy Hollow NY.
4. Walk Across the Tarrytown–Sleepy Hollow Border
Sleepy Hollow and its neighbor, Tarrytown, sit side by side along the Hudson River, and exploring both makes for a rich experience. The two villages share history, shops, and restaurants.
One highlight is the Tarrytown Music Hall, one of the oldest theaters in the country. Another is the charming Main Street with boutique stores and cozy cafés. Just a short stroll from Sleepy Hollow, this area broadens your trip and adds variety to your list of things to do in Sleepy Hollow NY.
5. Take a Scenic Stroll Along the Hudson River
For travelers who enjoy the outdoors, Sleepy Hollow offers breathtaking river views. The Hudson River Walk at Kingsland Point Park provides a peaceful escape with walking paths, picnic areas, and open spaces.
The park is also home to the historic Tarrytown Lighthouse, a cast-iron beacon that has stood since the late 19th century. Bring a camera for postcard-worthy shots of the river, bridge, and skyline. Enjoying the waterfront is one of the most relaxing things to do in Sleepy Hollow NY, especially during sunrise or sunset.
6. Tour the Old Dutch Church
Dating back to the late 1600s, the Old Dutch Church is one of the oldest in New York and central to Irving’s Legend of Sleepy Hollow. The small stone church and its adjacent burial ground inspire a sense of timelessness.
You can take a guided tour to learn about its history and connections to the famous story. Attending a service or concert here is also a memorable way to engage with the community. For literature fans and history lovers, the Old Dutch Church is a highlight among things to do in Sleepy Hollow NY.
7. Indulge in Local Food and Drink
A trip to Sleepy Hollow isn’t complete without sampling its food scene. From casual diners to upscale restaurants, the village offers something for every palate. RiverMarket Bar & Kitchen serves farm-to-table dishes with Hudson Valley ingredients, while Horsefeathers is a cozy spot for hearty American classics.
If you’re a fan of craft beer, check out local breweries and bars in nearby Tarrytown. Pairing your adventures with good food is always one of the tastiest things to do in Sleepy Hollow NY.
8. Discover Rockefeller State Park Preserve
Just a short drive from Sleepy Hollow, this preserve features over 1,400 acres of meadows, woodlands, and lakes. It’s perfect for hiking, birdwatching, or simply soaking in nature.
The trails wind through forests and along scenic carriage roads built by the Rockefeller family. Fall foliage here is spectacular, making it one of the best outdoor things to do in Sleepy Hollow NY.
9. Step Into Washington Irving’s Sunnyside
Although technically in Tarrytown, Washington Irving’s Sunnyside is essential to any Sleepy Hollow itinerary. The famous author’s picturesque home sits on the Hudson River, with Gothic Revival architecture and beautifully landscaped grounds.
Guided tours offer insights into Irving’s life, works, and the cultural impact of The Legend of Sleepy Hollow. For literary enthusiasts, this visit is one of the most inspiring things to do in Sleepy Hollow NY.
10. Celebrate Year-Round Events
Beyond Halloween, Sleepy Hollow hosts events all year. Holiday markets, music festivals, and community fairs bring locals and visitors together. Seasonal farmers’ markets offer fresh produce and artisanal goods, while summer concerts light up the evenings.
Checking the event calendar before your trip ensures you won’t miss out. Participating in local celebrations ranks high among the most authentic things to do in Sleepy Hollow NY.
Travel Tips for Visiting Sleepy Hollow
- Best Time to Visit: October is the most festive, but spring and summer provide quieter charm.
- Getting There: Sleepy Hollow is about 30 miles north of Manhattan, easily accessible by car or train.
- Where to Stay: Options include boutique inns, riverfront hotels, and cozy B&Bs in both Sleepy Hollow and Tarrytown.
- Parking: Popular attractions, especially in fall, fill up quickly—arrive early.
Final Thoughts
From legendary tales to peaceful river walks, the variety of things to do in Sleepy Hollow NY makes it a destination worth exploring. The village balances its spooky reputation with genuine history, natural beauty, and community warmth. Whether you’re chasing the ghostly Headless Horseman, hiking scenic trails, or sampling local cuisine, Sleepy Hollow promises experiences you won’t soon forget.