Sleepy Hollow Travel Guide

Discover the best places to visit, eat, and stay in Sleepy Hollow, New York.


Introduction to Sleepy Hollow

Located in Westchester County of New York, Sleepy Hollow is a charming village famous for its legendary tale “The Legend of Sleepy Hollow” written by renowned author Washington Irving. Sleepy Hollow is a quaint and picturesque destination, sitting on the eastern bank of the Hudson River, providing visitors with an opportunity to take a break from their mundane routine and explore its cultural and natural attractions.

List of Places to Visit in Sleepy Hollow

Culturally Important Attractions: Museums and Historical Places

Sleepy Hollow Cemetery

The Sleepy Hollow Cemetery is a peaceful and serene resting place known for its rich history and breathtaking views. Famous personalities, including Andrew Carnegie, Elizabeth Arden, and Walter Chrysler, are buried here. The cemetery is unlike any other, with winding roads, picturesque landscapes and incredible history for visitors to explore.

Washington Irving’s Sunnyside

Washington Irving’s Sunnyside, the Tarrytown resident’s home, is now a beautiful museum that showcases the life and works of Irving himself. Here, visitors can take guided tours of the home and learn about Irving’s creation of the legendary tale of Sleepy Hollow.

Philipsburg Manor

Philipsburg Manor is a preserved seventeenth-century farm that resembles the era of colonial times. Visitors can take a guided tour of the property and see demonstrations of cooking within the colonial era.

Natural Attractions of Sleepy Hollow: Outdoor Adventures and Scenic Views

Rockefeller State Park Preserve

Rockefeller State Park Preserve is a paradise for nature enthusiasts and hikers, containing over 1800 acres of picturesque scenery and walking trails. Diverse wildlife and beautiful views make this park an ideal place for a picnic or a relaxing stroll.

The Old Croton Aqueduct Trail

The Old Croton Aqueduct Trail is a historic trail that follows an old waterway, allowing visitors to see a unique perspective of the natural beauty of Sleepy Hollow. Walking along the trail allows hikers to experience a unique section of this historic trough.

The Hudson River

The Hudson River is a prominent feature of the Sleepy Hollow area and can be accessed via multiple observation decks, which provide impeccable views. For more adventurous visitors, arranging a kayaking excursion would be an excellent opportunity to see the Hudson from a different perspective.

Hiking/Biking Routes of Sleepy Hollow

The Leatherman’s Loop Trail

The Leatherman’s Loop Trail is one of the most popular hiking trails in Sleepy Hollow, stretching over 6.5 miles of beautiful scenery. The trail is relatively tough, but it’s filled with many natural landmarks, including the indigenous Popolopen Creek and picturesque hilly terrain.

The Sleepy Hollow Mountain Bike Trail

The Sleepy Hollow Mountain Bike Trail is the ideal trail for mountain bikers. The trail is well maintained to provide a perfect biking experience and showcases excellent views of the Hudson River.

Best Things to Do in Sleepy Hollow: Activities and Tours

Horse Riding in the Forest

Majestic trails of the Rockefeller State Park Preserve are ideal for horseback riding. A local stable in Sleepy Hollow provides guided riding tours for visitors to explore the natural beauty of the preserved forest.

Tarrytown Music Hall

The Tarrytown Music Hall is a historical venue for live performances that offers an astounding experience with a more intimate feel. Multiple genres and performances are available throughout the year.

Week-Long Itinerary for Sleepy Hollow

Day 1 Day 2 Day 3 Day 4 Day 5
Sleepy Hollow Cemetery Horse Riding in Forest Philipsburg Manor Washington Irving’s Sunnyside The Hudson River
The Leatherman’s Loop The Old Croton Aqueduct Trail Tarrytown Music Hall Rockerfeller State Park Preserve The Sleepy Hollow Mountain Bike Trail
Breakfast at Sweet Grass Breakfast at Lefteris Gyro Breakfast at Coffee Labs Breakfast at The Jolly Onion Breakfast at Horsefeathers

Food and Drink Scene of Sleepy Hollow

Must-Try Dishes

The Horseman Restaurant

The Horseman Restaurant is a go-to dining destination in Sleepy Hollow. Their take on classic American dishes with a farm-to-table touch has put them on the culinary world’s radar. The signature dish is the Sleepy Hollow Pie - a blend of grass-fed beef with a unique blend of flavors unique to the restaurant itself.

The Twisted Oak Restaurant

The Twisted Oak Restaurant is an upscale French restaurant located in Sleepy Hollow that provides an exquisite culinary experience for their guests. Must-tries include escargots, roasted duck, and the chocolate soufflé.

Local Beverages

Bridge View Tavern

Bridge View Tavern is nestled in the heart of Sleepy Hollow village, serving handcrafted beers, delightful cocktails, and a great atmosphere. Their signature cocktails include the Vanilla Latte Martini and the Sparkling Pear.

RiverMarket Bar & Kitchen

RiverMarket Bar & Kitchen is a chic waterfront restaurant, known for its creative cocktails, unique wine collection, and exquisite dishes. The Signature cocktail - the Sleepy Hollow Sour, is a concoction of Westchester-distilled bourbon, honey, fresh lemon juice, and bitters.

Where to Stay in Sleepy Hollow: Hotels, Hostels, and Guesthouses

Tarrytown House Estate on the Hudson

Tarrytown House Estate on the Hudson is an elegant and chic hotel, offering a once-in-a-lifetime experience to its guests. The hotel has over 200 various rooms, suites, and guesthouses, which provides an opportunity for travelers to experience the best of Sleepy Hollow.

Castle Hotel & Spa

Castle Hotel & Spa is a hotel that resembles a medieval castle, equipped with all modern amenities to provide a royal experience. Their pristine rooms, fine dining, spa, and excellent service ensures a luxurious stay.

What to Buy in Sleepy Hollow: Souvenirs and Local Products to Bring Home

Local artists and vendors create the perfect souvenir selection of Sleepy Hollow influenced merchandise. Gourmet chocolates, locally made handcrafted pottery, and one-of-a-kind Halloween-themed decorations are the must-buy souvenirs.

Local Culture and Customs of Sleepy Hollow

Halloween is a significant festival for the residents of Sleepy Hollow and the surrounding areas. Sleepy Hollow is home to many Halloween-themed events, including the Great Jack O’Lantern Blaze at Van Cortlandt Manor and the Horseman’s Hollow haunted house experience.

Best Time to Visit Sleepy Hollow

The autumn season is the peak time to visit Sleepy Hollow. The fall foliage, Halloween festivities, and crisp air make for a perfect seasonal trip. Summers, however, are also a great time to visit with vibrant blooming flowers and warm weather activities, including horseback riding and hiking.

Do’s and Don’ts of Sleepy Hollow

Do:

  • Respect the rich cultural heritage of Sleepy Hollow and its tranquil cemeteries.
  • Consider going on guided tours to have a better understanding of the culture and history of Sleepy Hollow.
  • Take a leisurely stroll through the village to soak in the picturesque views.
  • Enjoy the local food and drinks, especially the Sleepy Hollow Pie and Twisted Oak cocktails.

Don’t:

  • Litter, damage, or disturb the natural and man-made surroundings.
  • Skip the historic sites or museums as they’re significant to the village’s cultural identity.
  • Disrupt the privacy of locals or the peace the village offers.

Safety and Health

Safety in Sleepy Hollow

Sleepy Hollow is a safe place to visit with low crime rates. However, it’s recommendable to take requisite measures to keep yourself safe, including keeping your belongings secure, especially when out for a picnic or hiking.

Health in Sleepy Hollow

The medical facilities in Sleepy Hollow are well-equipped, and good healthcare is easily accessible. In case of an emergency, contact 911 or visit the Sleepy Hollow Ambulatory Surgery Center.

Getting to Sleepy Hollow: Transportation Options and Logistics

Airports Near Sleepy Hollow

  • Westchester County Airport
  • John F. Kennedy International Airport

Bus Stations Near Sleepy Hollow

  • Tarrytown Station
  • Philipsburg Manor State Historic Site

Other Options

For those who prefer driving, there are ample parking options available. Moreover, some visitors also opt for bike rentals to explore the village’s natural beauty.

How to Get Around in Sleepy Hollow

Sleepy Hollow is a relatively small village, and it’s easy to navigate on foot or bike. For those who prefer not to walk, taxis and car rentals are available.

Where to Go Next from Sleepy Hollow: Nearby Destinations and Excursions

  • The Rockefeller Estate, Kykuit – Tarrytown
  • Hudson Valley Center for Contemporary Art - Peekskill
  • Storm King Art Center – New Windsor
  • Dia Beacon - Beacon

Conclusion

Sleepy Hollow is a historically rich and culturally significant village that offers visitors unforgettable experiences ranging from tours, hiking, and great food. From its scenic nature trails to its spooky haunted house experiences, there’s something for everyone in Sleepy Hollow. Slow down, take in the beauty, and experience this unique village in the Hudson Valley.

The mill and millpond at Philipsburg Manor. The mill and millpond at Philipsburg Manor. Old Dutch Church of Sleepy Hollow Old Dutch Church of Sleepy Hollow Sleepy Hollow Cemetery Sleepy Hollow Cemetery Patriot's Park Patriot's Park