Sleepy Hollow, a small village located just 30 miles north of New York City, is best known for its connection to Washington Irving’s classic tale, “The Legend of Sleepy Hollow.” Situated along the Hudson River, the village has a population of about 10,000. While it is known for its spooky legends and historic connections to Irving’s story, Sleepy Hollow is also a place of natural beauty.
The village features lush green landscapes, rolling hills, and picturesque river views. It is home to the famous Sleepy Hollow Cemetery, where Washington Irving himself is buried. The town is full of charming, historic buildings and is a popular destination for those interested in the macabre as well as American folklore.
Beyond its famous literary association, Sleepy Hollow is a vibrant community with a rich history, offering visitors a glimpse into 18th and 19th-century life in the United States. The town blends its spooky charm with serene, natural beauty.
Looking for what to do here? Check out the best and fun things to do when you visit.
Things To Do In Sleepy Hollow, NY
1. Visit the Sleepy Hollow Cemetery
Sleepy Hollow Cemetery
The Sleepy Hollow Cemetery is a beautiful and historic place to explore. It was established in 1849 and is the final resting place of many notable figures. Among them is Washington Irving, the famous author of “The Legend of Sleepy Hollow”. This cemetery features stunning landscapes and intricate gravestones.
Walking through the cemetery, you can admire the Gothic architecture of the tombs and the serene atmosphere. Additionally, the expansive grounds offer lovely views of the surrounding hills and Hudson River. Guided tours are available, sharing stories behind the graves and the importance of the site.
This cemetery is a perfect blend of history and tranquility. It’s an excellent spot for photography enthusiasts as well. The fall season enhances its charm with vibrant foliage creating a picturesque view.
Many visitors come to reminisce about the stories associated with the characters buried here. Exploring Sleepy Hollow Cemetery immerses you in the area’s rich heritage.
Do not miss the chance to visit this scenic cemetery, which brings history to life in a peaceful setting.
Address: 540 N Broadway, Sleepy Hollow, NY 10591.
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2. Explore the Old Dutch Church
The Old Dutch Church is a historic gem situated in Sleepy Hollow. It dates back to the 17th century and offers a glimpse into the area’s colonial past. The church’s architecture is striking, featuring a simple yet beautiful design.
Visitors can wander around the church grounds, which are adjacent to the cemetery. The churchyard is as enchanting as the church itself, with ancient trees and historic gravestones. Educational programs and special services are often held here, making it a vibrant part of the community.
The church also connects to the storytelling aspect of Sleepy Hollow, as it is mentioned in Washington Irving’s famous tale. You can take a self-guided tour to learn more about the church’s history and significance.
The tranquil atmosphere makes it a perfect spot for reflection. Whether you admire the architecture or ponder over its history, the Old Dutch Church is an enriching experience.
Address: 430 N Broadway, Sleepy Hollow, NY 10591.
3. Tour the Philipsburg Manor
Philipsburg Manor is a marvelous historic site in Sleepy Hollow. This restored 18th-century manor provides insight into colonial life. It is part of the Sneden’s Landing Historic District, offering guided tours and educational programs about its history.
The estate includes beautiful gardens and a working gristmill, which are available for visitors to explore. During tours, guests hear fascinating stories about the Philips family and the enslaved people who lived and worked on the estate, enriching the understanding of the region’s past.
Philipsburg Manor also hosts seasonal events and activities that engage visitors of all ages. For children, there are interactive programs that focus on history and cooking methods of the period. It’s a great learning experience for families.
The scenic Hudson River backdrop makes it an ideal spot for leisurely walks. Take your time to enjoy the historic architecture while absorbing the enchanting views.
Address: 381 N Broadway, Sleepy Hollow, NY 10591.
4. Hike at the Rockefeller State Park Preserve
Rockefeller State Park Preserve is a beautiful natural haven in Sleepy Hollow. The preserve features miles of well-maintained hiking trails that wind through lush forests and meadows. It’s an ideal place for outdoor enthusiasts and families looking to enjoy nature.
While hiking, you can observe various species of wildlife and enjoy scenic views of the Hudson River. The peaceful ambiance makes it perfect for picnicking as well. The park is pet-friendly, allowing you to explore with your furry friends.
In the fall, the foliage creates a spectacular backdrop for hiking. Various trails offer different difficulty levels, so there’s something for everyone. You can spend a day exploring or simply take a leisurely walk.
Many visitors also enjoy the serene environment for meditation or quiet reflection. The blend of wildlife and picturesque scenery creates a rejuvenating experience.
Address: 355 S Broadway, Sleepy Hollow, NY 10591.
5. Experience the Legend of Sleepy Hollow at Kykuit
Kykuit is the historic estate of the Rockefeller family, located in nearby Sleepy Hollow. This grand estate offers a glimpse into the lives of one of America’s most prominent families. Guided tours showcase the stunning art collections and beautifully landscaped gardens.
Visitors can learn about the legendary stories tied to the estate, connecting it to Washington Irving’s works. The estate’s architecture is remarkable, with views that overlook the Hudson River. Many find the gardens to be particularly enchanting.
In addition to the main house, the estate features various sculptures and outdoor exhibits. It’s also a wonderful location for photographs, capturing the beauty of both nature and architecture.
Attending special events and performances held at Kykuit adds to the experience. The estate becomes a lively venue for art and culture, bringing history to life.
Address: 381 N Broadway, Sleepy Hollow, NY 10591.
6. Take a bike ride along the Hudson River Greenway
The Hudson River Greenway is an excellent route for cyclists looking to enjoy stunning river views. The path is well-maintained and runs alongside the Hudson River, providing an enjoyable biking experience. You can take in the scenery while biking through beautiful parks and charming towns.
This greenway connects various attractions, making it convenient to plan a full day of exploration. There are ample benches and picnic spots along the way for breaks and scenic views. The fresh air and natural surroundings add to the joy of cycling.
Accessibility is another bonus, as the greenway caters to cyclists of all skill levels. Whether you’re a novice or an experienced rider, you’ll find suitable paths for a satisfying ride.
The fall colors enhance the route’s beauty, attracting both local riders and visitors. Bring a camera to capture memorable moments and enjoy the tranquility of the Hudson River.
Address: 1 Pine St, Tarrytown, NY 10591.
7. Discover the Sleepy Hollow Lighthouse
The Sleepy Hollow Lighthouse, also known as the Tarrytown Lighthouse, is a charming beacon located on the Hudson River. Although it’s mostly a functioning lighthouse, visitors can enjoy the picturesque views from the shore. It offers a perfect photo opportunity, especially during sunrise or sunset.
The lighthouse is rich in history and adds to the charm of the area. You can learn about its significance and role in guiding river traffic. Picnicking by the shore and watching boats glide past is also a popular activity.
Nearby parks provide additional scenic spots, making it a great outing for families. Kids can play while adults relax or explore the surrounding areas.
Many events take place nearby, contributing to the area’s lively atmosphere. From outdoor concerts to community celebrations, the lighthouse area buzzes with activity.
Address: Tarrytown, NY 10591.
8. Enjoy the views at Hook Mountain State Park
Hook Mountain State Park offers breathtaking views of the Hudson River and its surrounding landscapes. The park is a hotspot for hiking and picnicking, making it perfect for a day out in nature. The trails lead you to stunning viewpoints and varying terrains.
Birdwatchers and nature enthusiasts will especially appreciate the rich biodiversity of the area. The park is home to many species of birds and wildlife. Different trails cater to all levels of hikers, ensuring everyone can enjoy the beauty of the park.
In addition to hiking, Hook Mountain is popular for mountain biking. The trails provide diverse routes suitable for adventurous explorers. Autumn is particularly spectacular here, as the foliage transforms into vibrant colors.
The peaceful setting makes it a fantastic spot for a quiet retreat. Feel free to pack a lunch and enjoy the scenic beauty from a hilltop.
Address: 5 Hook Mountain Rd, Nyack, NY 10960.
9. Visit the Van Cortlandt Manor
Van Cortlandt Manor is a beautifully restored historic site and museum that provides insight into the Hudson Valley’s colonial past. The manor dates back to the 18th century and offers guided tours through its rooms, where you’ll learn about early American life.
The grounds include picturesque gardens and stunning views of the Hudson River, making it a great place to stroll and relax. You can attend various educational programs, historical reenactments, and special events throughout the year.
The manor’s architecture captures the elegance of the time, and there are often hands-on activities for children and families. Engaging exhibits provide additional information about the Van Cortlandt family and their contributions to the region.
Make sure to explore the surrounding area, which is rich in history and natural beauty. Van Cortlandt Manor promises a fun and informative day for visitors of all ages.
Address: 525 S Broadway, Sleepy Hollow, NY 10591.
10. Attend the annual Sleepy Hollow Halloween Festival
The Sleepy Hollow Halloween Festival is a highlight for visitors each fall. This exciting event draws locals and tourists alike, wanting to immerse themselves in Halloween spirit. Activities include face painting, hayrides, and themed performances for families.
The festival celebrates the legacy of Washington Irving, making it a unique attraction. Costumed characters welcome you, enhancing the festive atmosphere. Various vendors offer seasonal treats and crafts, providing a magical experience for attendees.
The highlight is often the storytelling or reenactments of “The Legend of Sleepy Hollow,” capturing the essence of the tale. There are also games and fun activities for children, making it an ideal family outing.
Whether you’re looking for thrills or simply enjoying the ambiance, the Halloween Festival is festive and entertaining. Don’t forget to take photos to remember your visit to this storied event!
Address: Sleepy Hollow, NY 10591.
11. Walk through the historic Old Dutch Burying Ground
The Old Dutch Burying Ground is a must-visit historical site in Sleepy Hollow. It dates back to the late 1600s and is the resting place of many early settlers. The cemetery is peaceful and atmospheric, perfect for a reflective stroll.
As you walk through the grounds, you’ll notice the unique and ornate gravestones, some of which date back over 300 years. Informational plaques describe the significance of various individuals buried here, including those mentioned in Washington Irving’s tales.
The surrounding trees and natural beauty create a serene environment, allowing for moments of tranquility. It’s an excellent location for photography, particularly during the fall when the foliage is vibrant.
Visitors often feel a sense of connection to the area’s history while wandering through this important site. Explore the stories behind the headstones and capture the essence of Sleepy Hollow’s past.
Address: 43 N Broadway, Sleepy Hollow, NY 10591.
12. Explore the Teen Witch pumpkin picking
Teen Witch pumpkin picking offers a fun family-friendly experience in the fall. This local tradition allows visitors to pick their pumpkins right from the fields. There’s something magical about wandering through rows of pumpkins waiting to be chosen.
In addition to pumpkin picking, the event often includes hayrides, farm games, and seasonal treats. Children and adults alike enjoy a chance to embrace the spirit of autumn while making lasting memories. Craft stations featuring fun activities are usually available to entertain the little ones.
Spending a day at Teen Witch is not only about pumpkins but also about bonding with family and friends. The festive atmosphere creates a sense of joy and excitement. Whether you’re carving pumpkins later or showcasing your finds at home, each pumpkin has a unique story.
This pumpkin picking experience highlights the importance of community and tradition during the fall season. Make sure to check it out during your visit!
Address: Sleepy Hollow, NY 10591.
13. Check out the Sleepy Hollow Arts & Crafts Fair
The Sleepy Hollow Arts & Crafts Fair is an excellent event for lovers of handmade goods. Local artisans showcase their talents, offering various crafts, jewelry, and fine art. This fair creates an opportunity to find unique gifts and support local artists.
Visitors can stroll through booths filled with creative offerings and enjoy the lively atmosphere. The fair typically includes refreshments, live music, and entertainment, ensuring a fun day for all ages. Kids have opportunities for hands-on activities, too, encouraging creativity.
Participating in this fair helps foster a sense of community involvement. It’s a place where locals and visitors come together to celebrate artistry and craftsmanship. You can learn about different creative processes by chatting with artisans.
Don’t miss this opportunity to encounter the vibrant artistic culture of Sleepy Hollow while exploring beautiful crafts!
Address: Sleepy Hollow, NY 10591.
14. Experience the Great Jack O’Lantern Blaze
The Great Jack O’Lantern Blaze is a remarkable autumn attraction. This enchanting event features thousands of intricately carved pumpkins displayed along a beautiful trail. Each pumpkin is crafted with care, creating a stunning visual experience after sunset.
Walking through the event, you’ll encounter themed displays, glowing pumpkins, and festive decorations. The meticulous artistry makes it a feast for the eyes. Families can enjoy live music and seasonal treats, which enhance the festive feel.
This annual event has become a beloved tradition, attracting both locals and visitors seeking fall fun. The ambiance feels almost magical as you wander through the rows of glowing pumpkins.
Bring your camera; the lights and creative designs will provide perfect photo opportunities. It’s a fantastic way to celebrate the season and return home with beautiful memories.
Address: 105 W 24th St, Sleepy Hollow, NY 10591.
15. Go fishing at Tarrytown Lakes
Tarrytown Lakes is a wonderful spot for fishing enthusiasts. This scenic location offers peaceful waters surrounded by natural beauty, making it ideal for a day of fishing or relaxing by the water. The lakes provide a range of fish species, ensuring a satisfying experience.
Many local anglers frequent Tarrytown Lakes for freshwater fishing. The area is well maintained and provides plenty of picturesque spots for casting a line. Bring your fishing gear and spend a leisurely day in nature.
Aside from fishing, the area allows for hiking, biking, and enjoying picnics. Families can create lasting memories while spending quality time outdoors. It’s a perfect getaway from the hustle and bustle of daily life.
The scenic surroundings also offer potential for photography, especially during sunrise and sunset. With lush trees and wildlife, Tarrytown Lakes is a true nature lover’s paradise.
Address: 85 N Broadway, Tarrytown, NY 10591.
16. Attend live performances at the Tarrytown Music Hall
The Tarrytown Music Hall is a beautifully restored venue hosting a variety of live performances. From concerts to theater productions, this intimate space guarantees an enjoyable experience for every attendee. The historic building adds to the charm of each event.
Regular shows feature local artists as well as renowned performers from various genres. The acoustics make it an excellent choice for music lovers, while supporting the local arts community all at once. The cozy setting ensures every seat offers a great view.
Before or after the shows, visitors can explore nearby restaurants and shops in Tarrytown. Make it an evening by dining out and enjoying the vibrant community atmosphere.
Check the calendar for upcoming events and join fellow community members in celebrating the arts. The Tarrytown Music Hall promises an entertaining and culturally enriching experience.
Address: 13 Main St, Tarrytown, NY 10591.
17. Explore the historic streets of the village
Exploring the historic streets of Sleepy Hollow is an experience unlike any other. The village is filled with charming architecture and picturesque landscapes. As you stroll through the streets, you’ll encounter a mix of historic buildings and captivating stories.
Each street has its own unique character and is lined with trees that enhance the beauty of the surroundings. Many buildings date back to the early 18th century. The ambiance is friendly and inviting, making it easy to enjoy walking through the community.
Make sure to visit the local shops and cafes that add to the charm of the village. Each stop offers the chance to engage with the community and possibly find unique souvenirs to take home.
Listening to local stories about the village’s history enriches your exploration. Embrace the enchanting aura of Sleepy Hollow as you discover its legacy in a relaxed setting.
Address: Sleepy Hollow, NY 10591.
18. Dine at local restaurants with a river view
Dining at local restaurants with a river view offers a delightful experience in Sleepy Hollow. Several eateries line the Hudson River, providing stunning vistas alongside delicious meals. Whether you prefer casual or fine dining, you’ll find something to satisfy your palate.
The menu items often feature local ingredients, giving a taste of the region. Enjoy fresh seafood or farm-to-table dishes as you gaze over the beautiful waters of the Hudson. Many restaurants offer outdoor seating during the warmer months, enhancing the experience.
Pair your meals with local wines and craft beers, making for a perfect dining experience. It’s an excellent way to relax after a day of exploration, allowing you to unwind while taking in charming views.
Don’t forget to check for specials or live entertainment nights. This makes for a vibrant dining atmosphere where you can mingle with locals and visitors alike.
Address: Sleepy Hollow, NY 10591.
19. Visit Washington Irving’s Sunnyside
Washington Irving’s Sunnyside is a historic home located in Sleepy Hollow, offering tours of the charming estate. Irving, the famous author, wrote “The Legend of Sleepy Hollow” in this home. The picturesque property gives visitors a glimpse into the life of the author and the inspirations behind his works.
The home’s architecture features whimsical elements, creating a cozy and inviting atmosphere. Guided tours cover Irving’s literary contributions and his lifestyle during the 19th century.
Guests can also explore the exquisite gardens and grounds surrounding the house. The scenic vistas add to the charm, making it a lovely spot for photography and reflection.
Special events throughout the year, like literary readings and seasonal festivities, bring the enchanting world of Irving to life. Make sure to visit Sunnyside for a fascinating journey into Sleepy Hollow’s cultural heritage.
Address: 3 W Sunnyside Ln, Irvington, NY 10533.
20. Attend the Sleepy Hollow Farmers Market
The Sleepy Hollow Farmers Market is a great place to experience local offerings. Held weekly, the market features fresh produce from nearby farms, handmade goods, and local crafts. It’s an excellent way to support the community and enjoy the bounties of the Hudson Valley.
Visitors can find seasonal fruits, vegetables, and baked goods, making it easy to shop for healthy meals. Local artisans also showcase their crafts, offering unique handmade items for purchase.
The market typically features live music, creating a lively atmosphere for families and friends to enjoy. Children can participate in fun activities while adults browse the stalls.
Overall, the farmers market is a wonderful connection to the community, allowing visitors to immerse themselves in local culture. Don’t miss this chance to gather fresh ingredients and enjoy artisanal finds while soaking in the vibrant community spirit.
Address: 5 Riverside Ave, Sleepy Hollow, NY 10591.
21. Explore the Hudson River Museum
The Hudson River Museum is an excellent destination for art and history lovers. It features compelling exhibitions that focus on the region’s cultural and natural heritage. The museum houses wonderful collections, including works by local artists and impressive historical artifacts.
Its galleries provide a deep insight into the artistic community of the Hudson River Valley. The museum often hosts special exhibitions, educational programs, and events for visitors of all ages. These programs enrich your understanding of both art and environmental science.
Outdoor activities include the museum’s scenic gardens, which provide beautiful views of the waterfront, enhancing your visit. There’s often live music and educational events in the gardens, allowing for a vibrant community atmosphere.
Whether you come for the art, history, or scenic views, the Hudson River Museum promises a rewarding experience.
Address: 511 Warburton Ave, Yonkers, NY 10701.
22. Take a guided ghost tour
Taking a guided ghost tour in Sleepy Hollow offers a thrilling way to experience the area’s haunted history. Join knowledgeable guides who share stories of the supernatural and local legends. The tour often includes visits to historic sites, adding a layer of intrigue to the experience.
Walking through the dimly lit streets and exploring the haunted locations, you’ll get a sense of the eerie atmosphere that surrounds Sleepy Hollow. Listen to tales of ghostly encounters and the many legends that have emerged over centuries.
These tours are particularly popular in the fall, adding a bit of spooky fun to your visit. Visitors from all ages enjoy the storytelling and immersive experience. Dress warmly and bring a flashlight for an even more authentic spooky experience.
For those interested in history and the supernatural, a ghost tour is an unforgettable addition to your Sleepy Hollow adventure.
Address: Sleepy Hollow, NY 10591.
23. Visit the Sleepy Hollow Performing Arts Center
The Sleepy Hollow Performing Arts Center is a vibrant venue for community performances and events. It showcases talented local artists and provides a platform for various artistic expressions, including theater, music, and dance.
With a focus on community involvement, attending a performance here is a great way to support local talent. The intimate setting allows for a unique experience where you can connect with the performers.
Regular programming includes family-friendly productions that engage audiences of all ages. The center hosts special events and seasonal performances that make for memorable evenings out.
Engage with the spirit of the community by attending shows or even participating in workshops. The Performing Arts Center enriches the local cultural scene, providing a relevant and entertaining experience.
Address: 13 Main St, Tarrytown, NY 10591.
24. Kayak on the Hudson River
Kayaking on the Hudson River offers a unique perspective of Sleepy Hollow’s beauty. Experience the tranquility of paddling along the river while enjoying breathtaking views of the landscape. Rentals are available, making it easy to get started.
Many guided kayaking tours are offered, allowing you to explore hidden coves and learn about local wildlife. The paddling experience provides a sense of adventure and connection to nature. You can spot various species of birds and river life along the way.
The river’s calm waters make it accessible for paddlers of all skill levels, and it provides a fantastic outdoor workout. As you navigate, enjoy the picturesque surroundings, especially during sunrise or sunset when the scenery is stunning.
Don’t miss the chance to connect with the river and appreciate the breathtaking views it offers.
Address: Sleepy Hollow, NY 10591.
25. Check out the local boutiques and shops
Exploring local boutiques and shops in Sleepy Hollow reveals unique treasures and charming finds. The area is home to a variety of shops, from antique stores to specialty boutiques. You’ll encounter welcoming storefronts filled with handcrafted items and local art.
Support the local economy by purchasing souvenirs and gifts that genuinely represent the town. Many shops offer items that reflect the spirit of Sleepy Hollow, including seasonal decorations, artwork, and more.
Shopping in Sleepy Hollow provides a relaxed atmosphere perfect for leisurely browsing. Make sure to chat with the friendly store owners and learn about their inspirations for their products.
Local cafes and restaurants are often nearby, allowing you to take a break and treat yourself after a shopping spree. Enjoy the neighborhood charm as you explore and find something special to take home.
Address: Sleepy Hollow, NY 10591.
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Final Thoughts
Sleepy Hollow, NY, is a captivating destination that seamlessly blends history, culture, and the beauty of nature. Whether you’re wandering through its historic streets or enjoying breathtaking views of the Hudson River, Sleepy Hollow invites exploration and discovery at every turn.
From guided tours that delve into local legends and beautiful parks for outdoor activities to charming boutiques and eateries with stunning vistas, there is something for everyone. Experiencing Sleepy Hollow is not just about its rich literary heritage; it’s about making memories in a picturesque environment.
As you leave, the echoes of its legends and the scenic splendor will linger in your heart, beckoning you to return to this enchanting corner of the Hudson Valley.