Sleepy Hollow, NY, is a charming town that is famous for its spooky legends and beautiful landscapes. Nestled along the banks of the Hudson River, this historic area offers a mix of fun activities for everyone. From scenic parks to interesting museums, there’s something for every visitor to enjoy. You can feel the magic in the air as you wander through its picturesque streets and lush greenery.
Today, we’ll look at some of the top things to do in Sleepy Hollow. Whether you’re visiting for the ghost stories or to enjoy nature, you’ll find plenty of exciting sights and activities to fill your day. Let’s get started on your adventure in this enchanting village!
Things To Do In Sleepy Hollow Ny
1. Visit the Historic Sleepy Hollow Cemetery
The Sleepy Hollow Cemetery is rich in history and intrigue. This beautiful resting place is home to many notable figures, including Washington Irving, the author of “The Legend of Sleepy Hollow.” It offers a peaceful ambiance for reflection and exploration.
As you wander the winding paths, notice the unique gravestones and monuments. Each tells a story of its own. The combination of nature and art creates a serene atmosphere, perfect for a leisurely stroll.
Don’t forget to stop by Washington Irving’s grave. It’s a special highlight for fans of his work. You can also find graves of other prominent individuals, making history come alive in this scenic location.
Guided tours are available during the summer months. They provide fascinating insights into the lives of those interred here. You’ll learn how Sleepy Hollow inspired so many tales and legends.
Visiting Sleepy Hollow Cemetery is more than a trip to a graveyard; it’s a deep dive into history and culture. Come and connect with the past in this historic site.
Address: 540 N Broadway, Sleepy Hollow, NY 10591.
2. Tour the Kykuit, the Rockefeller Estate
Kykuit, the stunning Rockefeller Estate, is a must-visit when in Sleepy Hollow. Nestled on a hilltop, it boasts beautiful gardens and impressive art collections. The estate combines natural beauty with architectural elegance in every corner.
Guided tours offer insights into the Rockefeller family and their legacy. You’ll explore the opulent mansion and learn about its historical significance. Each room is filled with interesting artifacts and art, from old masters to modern pieces.
Stroll through the beautifully manicured gardens. They feature terraces, sculptures, and incredible views of the Hudson River valley. The gardens are a great spot for photography or simply enjoying nature’s beauty.
Be sure to check out the underground art gallery. This gallery showcases unique sculptures and installations. Visitors rave about the breathtaking surroundings and fascinating history the estate offers.
A visit to Kykuit is more than just a tour; it’s an intriguing journey into history and artistry within a breathtaking landscape. Don’t miss this enchanting destination.
Address: 381 N Broadway, Sleepy Hollow, NY 10591.
3. Walk Through the Scenic Phillipsburg Manor
Phillipsburg Manor is a historic site that should be on your list. This riverfront plantation offers a glimpse into colonial life in the 18th century. It features several well-preserved buildings and lush nature trails, making it a relaxing trip for families.
As you explore the grounds, join one of the engaging demonstrations. These reenactments give you insight into daily life and the history of the region. You’ll learn about the milling process and see how the manor functioned in its prime.
The pathways around the manor wind through beautiful landscapes. It’s a perfect spot for nature lovers, with opportunities for hiking and bird watching. The peaceful atmosphere invites you to take your time and soak in the surroundings.
Visiting Phillipsburg Manor is educational and enjoyable. It provides a unique perspective on craftsmanship and agriculture of the time. Kids and adults alike will love participating in hands-on activities.
Plan your visit to Phillipsburg Manor and experience a piece of history in a serene setting. Your journey through time awaits!
Address: 45 Phillipsburg Manor Ln, Sleepy Hollow, NY 10591.
4. Enjoy a Boat Tour on the Tarrytown Lakes
A boat tour on the Tarrytown Lakes offers a delightful way to experience the Hudson Valley. Immerse yourself in the beautiful scenery as you glide across the water. This cruise provides stunning views of the landscape, making it a perfect family outing.
During your boat tour, keep an eye out for local wildlife. You may see birds, fish, and occasionally a deer by the lakeside. The natural beauty surrounding the lakes is truly breathtaking, especially during sunset.
Learn about the history of the area from knowledgeable guides. Their stories add depth to your experience, making it informative and enjoyable. It’s not just a scenic trip, but a lesson in local history.
Consider bringing a picnic to enjoy on the boat or by the lakeside afterward. It’s a great way to relax and soak in the sights and sounds of nature. Make sure to bring your camera; you’ll want to capture the memories!
Join a boat tour on Tarrytown Lakes for a fun and scenic experience. Perfect for all ages, it’s a wonderful way to enjoy the serenity of the Hudson River area.
Address: Tarrytown Lakes, NY 10591.
5. Discover the Story of the Headless Horseman at the Sleepy Hollow Farmer’s Market
The Sleepy Hollow Farmer’s Market is a vibrant spot to visit, especially for fans of local produce and culture. Each season, the market comes alive with vendors selling fresh fruits, vegetables, and handmade goods. But there’s more than just food here!
Explore the local folklore surrounding the Headless Horseman. The market often features storytelling booths, where you can listen to tales of this legendary character. Discover how the legend influenced literature and popular culture.
You can also find art inspired by the Headless Horseman. Local artists showcase their creations, which makes for wonderful souvenirs. Engage with the community and learn about their connection to this famous story.
The market is an excellent family-friendly destination. Kids will enjoy the upbeat atmosphere, and there are often activities just for them. It’s a great way to spend a Saturday morning in Sleepy Hollow.
Make a point to visit the Sleepy Hollow Farmer’s Market for a taste of the local culture and connection to history. It’s a delightful way to immerse yourself in the community while experiencing the legend of the Headless Horseman.
Address: 100 Siegel St, Sleepy Hollow, NY 10591.
6. Hike the Trails of the Rockefeller State Park Preserve
Rockefeller State Park Preserve offers magnificent hiking trails for outdoor enthusiasts. With over 1,000 acres of forests, streams, and meadows, you’ll enjoy nature at its best. The scenic views and varied terrain make every hike unique and refreshing.
Choose from numerous trails that cater to different skill levels. Whether you’re a beginner or an experienced hiker, there is something for everyone. Make sure to take your time to explore the charming landscapes along the way.
Wildlife enthusiasts will love spotting birds and other creatures in their natural habitat. The variety of ecosystems within the preserve provides perfect opportunities for wildlife watching. Grab your binoculars and catch a glimpse of the local fauna!
The trails are well-marked, making it easy to navigate. Bring your family or friends for an enjoyable day outdoors. Don’t forget to pack a picnic to savor amidst the beautiful surroundings.
Hiking at Rockefeller State Park Preserve is more than just exercise; it’s a way to connect with nature and enjoy the fresh air. Experience the beauty of Sleepy Hollow from the trails!
Address: 125 Phelps Way, Pleasantville, NY 10570.
7. Attend the Annual Great Jack O’ Lantern Blaze
The Great Jack O’ Lantern Blaze is a spectacular event that lights up Sleepy Hollow every fall. This dazzling display features thousands of intricately carved pumpkins, illuminating the night in a magical way. It’s perfect for all ages and attracts visitors from near and far.
As you stroll through the paths, enjoy the creativity of each pumpkin display. The artistry is breathtaking, with designs ranging from classic jack o’ lantern faces to elaborate sculptures. It’s a visual feast that will leave you in awe.
Live music and special activities enhance the festive atmosphere. Various vendors offer seasonal treats, making it a great place for a family outing. Warm cider and pumpkin-flavored snacks are must-tries!
Plan your visit wisely, as this event draws large crowds. Booking tickets in advance is recommended to ensure a smooth experience. It’s a beloved tradition that celebrates creativity and the spirit of Halloween.
Don’t miss the Great Jack O’ Lantern Blaze—a highlight of the fall season in Sleepy Hollow. It’s a memorable event for the whole family!
Address: 505 South Highland Ave, Sleepy Hollow, NY 10591.
8. Visit the Old Dutch Church
The Old Dutch Church is a historic landmark in Sleepy Hollow, steeped in rich history. This beautiful stone church dates back to 1685, making it one of the oldest in the region. Its charming architecture and serene atmosphere attract visitors year-round.
Explore the surroundings and admire the striking stained glass windows. Each window features unique designs that reflect the church’s long-standing heritage. The churchyard is the final resting place of many notable figures, including some from Washington Irving’s stories.
Learn about the church’s significant role in the local community. Guided tours are offered, providing fascinating insights into its history and architectural details. You will appreciate the blend of history and cultural significance.
Attend a service or community event for a unique experience. The Old Dutch Church is a place of worship, fostering connections among its members. Joining a service allows you to immerse yourself in the spiritual atmosphere.
A visit to the Old Dutch Church is a journey through time—a chance to appreciate history, art, and community spirit in one of Sleepy Hollow’s key landmarks.
Address: 430 N Broadway, Sleepy Hollow, NY 10591.
9. Take a Guided Ghost Tour
If you’re looking for something thrilling, take a guided ghost tour of Sleepy Hollow. The town is filled with spooky tales and haunted history, making it the perfect spot for a nighttime adventure. This tour immerses you in local legends and ghost stories.
As you walk through historic sites, your guide will share chilling experiences and eerie folklore. These stories bring the town’s past to life and keep everyone on the edge of their seats. You’ll gain a new appreciation for Sleepy Hollow’s haunted reputation.
Prepare for a fascinating mix of history and ghostly encounters. Many participants have reported feeling the presence of spirits. The charming, yet haunting vibe adds excitement to the experience.
Dress warmly, as ghost tours typically take place in the evening. It’s a spooky yet enjoyable way to explore the lesser-known corners of Sleepy Hollow while appreciating its haunted charm.
Don’t miss this unique adventure! A ghost tour is an unforgettable experience for thrill-seekers and history buffs alike. Prepare for a frightfully good time!
Address: 44 W 5th Ave, Bayonne, NJ 07002. Tours start from various locations
10. Explore the Sleepy Hollow Lighthouse
The Sleepy Hollow Lighthouse, also known as the Tarrytown Light, is a beautiful site worth visiting. This historic lighthouse stood tall since 1883, guiding ships along the Hudson River. It has been beautifully preserved and is an exciting landmark for history lovers and photographers alike.
The surrounding area is perfect for a leisurely stroll. Take in the fantastic views of the river and the picturesque landscape. The lighthouse is a popular subject for photography, especially during sunrise and sunset.
Plan your visit to time with a guided tour. You can learn about the operational history of the lighthouse, including its significance to navigation. It’s a chance to delve into maritime history while enjoying scenic views.
The lighthouse has a lovely setting for picnics, making it an ideal family outing. Bring your lunch to enjoy by the water while soaking in the tranquil surroundings.
Visiting the Sleepy Hollow Lighthouse is a great way to connect with the Hudson River’s history and beauty. Don’t forget your camera for spectacular photo opportunities!
Address: 98 Tarrytown Rd, Sleepy Hollow, NY 10591.
11. Participate in the Sleepy Hollow Winter Wonderland
During the holiday season, the Sleepy Hollow Winter Wonderland transforms the town into a festive paradise. This event features dazzling lights, seasonal activities, and opportunities for family fun. It’s a beloved holiday tradition that brings the community together.
Enjoy exciting attractions like ice skating and holiday-themed crafts. Kids can meet Santa Claus for photos and share their wish lists. The warm atmosphere is perfect for creating lasting holiday memories.
Stroll through the spectacular light displays. The twinkling lights and festive decorations spread holiday cheer across the town. It’s a magical experience that captures the spirit of the season.
Don’t miss the local vendors offering treats like hot cocoa and cookies. Enjoying delicious seasonal snacks adds to the festive experience. Prepare for a delightful evening filled with laughter and joy!
The Sleepy Hollow Winter Wonderland is an enchanting event that showcases the community’s holiday spirit. Bring your family and friends to celebrate the season in style!
Address: Sleepy Hollow, NY 10591.
12. Enjoy a Picnic at Kingsland Point Park
Kingsland Point Park is a lovely spot for a picnic and outdoor relaxation. This beautiful riverside park offers scenic views of the Hudson River and surrounding landscape. It’s a perfect place to unwind and enjoy nature with family and friends.
Spread out your blanket on the grassy areas and feast on your favorite picnic foods. The park has tables and benches for those who prefer a more structured dining experience. Take your time to savor the peaceful atmosphere and beautiful scenery.
Feel free to explore the park’s trails. You can walk or bike along the paths while taking in the fresh air. Nature enthusiasts will appreciate the variety of plants and wildlife in the area.
Kingsland Point Park is also a great spot for fishing or kayaking. Those looking for more action can rent equipment nearby and enjoy a day on the water. It’s a fun way to make the most of your time outdoors.
Plan a visit to Kingsland Point Park for a delightful picnic and outdoor adventure. It’s a beautiful escape in the heart of Sleepy Hollow!
Address: 55 Piermont Ave, Sleepy Hollow, NY 10591.
13. Experience the Breathtaking Views from the Sleepy Hollow High School Nature Trail
The Sleepy Hollow High School Nature Trail is an excellent destination for outdoor lovers. This well-maintained trail is perfect for walking, jogging, or simply enjoying nature. The views from the trail showcase the beautiful Hudson Valley and the surrounding landscapes.
As you hike, take in the fresh air and peaceful surroundings. The nature trail is surrounded by lush trees and greenery, providing a relaxing escape from the town’s hustle and bustle. It’s an ideal spot for a morning run or an afternoon walk.
Look for the various flora and fauna along the path. Birdwatchers will love the diverse wildlife in this serene area. The trail is a hidden gem for nature enthusiasts looking to explore the great outdoors.
Take your time on the trail and truly immerse yourself in the tranquil environment. Bring along your family for a fun and educational experience about local wildlife and plants.
Visit the Sleepy Hollow High School Nature Trail for a refreshing outdoor adventure. Enjoy the scenic views and the beauty of nature right in your community!
Address: 210 N Broadway, Sleepy Hollow, NY 10591.
14. Play a Round of Golf at the Sleepy Hollow Country Club
The Sleepy Hollow Country Club is not just for members—it’s an exceptional place for golf enthusiasts. Renowned for its stunning course, it offers a challenge for players of all skill levels. Set against the backdrop of the Hudson River, the scenery is unbeatable.
Experience the beautifully designed course that winds through the natural landscape. Each hole presents a unique challenge while providing breathtaking views. It’s an exciting way to enjoy a day outdoors with friends or family.
The club facilities are top-notch. After your game, relax in the inviting lounge or grab a bite to eat at the onsite restaurant. The atmosphere is friendly and welcoming, perfect for unwinding after a round of golf.
Consider joining one of the club’s social events or tournaments. It’s a chance to meet fellow golfers and make new friends while enjoying the beautiful surroundings.
Playing at Sleepy Hollow Country Club is more than just golf; it’s about making memories in a spectacular setting. Visit for a delightful day of sport and scenic beauty!
Address: 777 Albany Post Rd, Sleepy Hollow, NY 10591.
15. Visit the Local Shops and Eateries in the Charming Downtown Area
The downtown area of Sleepy Hollow is bursting with charm and character. Spend a day exploring the quaint shops and unique eateries that line the streets. It’s a perfect way to experience the local culture and find one-of-a-kind treasures.
From boutiques selling handmade crafts to specialty food shops, there’s something for everyone. You’ll enjoy discovering unique gifts and local artwork. Strolling through the streets offers a delightful mix of shopping and sightseeing.
Take a break at one of the local cafes or restaurants. Enjoy delicious meals, sweet treats, or warm beverages as you soak in the cozy atmosphere. The friendly staff add to the welcoming environment.
Check out the calendar of local events and festivals often held in downtown. These community gatherings bring residents and visitors together, showcasing the town’s vibrant spirit.
Visiting the local shops and eateries is a joyful experience that captures the essence of Sleepy Hollow. Plan your visit for a wonderful day of exploring and indulging in local flavors!
Address: Downtown Sleepy Hollow, NY 10591.
16. Take a Stroll Along the Hudson River Waterfront
The Hudson River Waterfront is a beautiful place to take a leisurely stroll and enjoy the serene atmosphere. The scenic views of the river and surrounding areas are perfect for relaxation and photography. It’s a fantastic way to unwind while soaking in the natural beauty of Sleepy Hollow.
Walking along the waterfront allows you to connect with nature while appreciating the stunning landscapes. You may even spot boats sailing by or wildlife along the riverbanks. The views change with the time of day, offering a different perspective at sunset or sunrise.
Accessible paths make it easy for everyone to enjoy a walk or bike ride. Bring a bicycle or rollerblades for a more active experience. The peaceful ambiance is perfect for a morning exercise routine or an evening unwind.
Pack a picnic to enjoy on one of the benches or grassy spots. Feeding the ducks and watching the swans are delightful activities for both kids and adults. It’s a great way to spend a day with family or friends.
Taking a stroll along the Hudson River Waterfront is a wonderful escape to enjoy the natural beauty of the area. Don’t miss out on this relaxing experience!
Address: 10 River St, Sleepy Hollow, NY 10591.
17. Attend a Performance at the Tarrytown Music Hall
The Tarrytown Music Hall is a cultural gem in Sleepy Hollow. This historic theater hosts various performances throughout the year, including concerts, theater productions, and film screenings. It’s a delightful venue that brings the community together through the arts.
With its stunning architecture and intimate atmosphere, every performance is a special experience. The seats offer excellent views no matter where you sit, making it a cozy setting to enjoy live entertainment. Check the schedule for upcoming shows to find something that interests you.
The theater also features a lovely bar and lounge area. Arrive early to relax and enjoy a drink before the show. It’s a wonderful way to start your evening out!
Don’t forget to bring your friends or family for a night of entertainment. Whether you’re a fan of music, theater, or film, you’ll discover something captivating at the Tarrytown Music Hall.
Attending a performance here is not just about the show; it’s about experiencing the vibrant local culture and arts scene. Make plans to enjoy a night out at this beloved venue!
Address: 13 Main St, Tarrytown, NY 10591.
18. Explore the Cultural Exhibits at the Sleepy Hollow Cultural Center
The Sleepy Hollow Cultural Center is a hub for art and culture in the community. This center houses various exhibits that showcase local artists and historical artifacts. It’s a wonderful place to immerse yourself in the area’s creative spirit.
Visit the center to discover rotating exhibitions featuring different art forms. From paintings to sculptures, each exhibit highlights the unique talents of local artists. It’s an inspiring experience for art lovers and casual visitors alike.
Look out for workshops and community events. The center often hosts art classes, lectures, and film screenings that encourage community engagement. Participating in these activities helps strengthen connections and fosters creativity.
The cultural center is family-friendly, making it a great educational outing for kids. It exposes them to the arts and encourages their own creativity. Don’t be surprised if you leave feeling inspired!
Take the time to visit the Sleepy Hollow Cultural Center for a glimpse into the local arts scene. It’s an experience that will enrich your visit to this charming town!
Address: 2 S Broadway, Sleepy Hollow, NY 10591.
19. Participate in Seasonal Festivals at the Sleepy Hollow Waterfront
The Sleepy Hollow Waterfront hosts various seasonal festivals throughout the year. These events celebrate local culture, traditions, and community spirit. It’s a perfect opportunity to enjoy festivities while connecting with the community.
From summer concerts to fall harvest festivals, there’s always something happening. Each festival features fun activities, live music, tasty food stalls, and local crafts. Bring your family and friends to enjoy the vibrant atmosphere.
These festivals often include activities for all ages. Kids can enjoy games and face painting, while adults explore local vendors and artisanal goods. The lively ambiance will keep everyone entertained.
Make sure to check the events calendar so you don’t miss out on popular festivals like the annual Halloween parade or summer concert series. Each event offers a delightful blend of fun, food, and community celebration.
Participating in seasonal festivals at the Sleepy Hollow Waterfront is an engaging way to experience local culture. Join in the festivities and create lasting memories with your loved ones!
Address: Sleepy Hollow Waterfront, NY 10591.
20. Enjoy an Evening Meal at a Riverfront Restaurant
Dining at one of the riverfront restaurants in Sleepy Hollow offers an extraordinary experience. Enjoying a meal with a view of the Hudson River creates a perfect ambiance for any occasion. Fresh flavors and stunning scenery make it a great stop after a day of exploring.
Choose from diverse cuisine options that cater to various tastes. You can find everything from Italian to American fare, with many restaurants emphasizing local ingredients. Each bite is a celebration of the region’s rich culinary heritage.
Don’t forget to try the house specials, often paired with a glass of wine from a local vineyard. The picturesque setting makes dining here a treat, especially during sunset when the sky fills with vibrant colors.
Many riverfront restaurants offer outdoor seating that allows you to savor the fresh air while enjoying scenic river views. It’s a wonderful way to enhance your dining experience!
Enjoying an evening meal at a riverfront restaurant is the perfect way to end your day in Sleepy Hollow. It’s not just about the food, but the entire experience of being surrounded by nature and good company.
Address: Various restaurants along the Hudson River, Sleepy Hollow, NY 10591.
Final Thoughts
Sleepy Hollow, New York, is a destination filled with rich history and natural beauty. Whether you are exploring the famous tales of the past, enjoying the vibrant local culture, or immersing yourself in captivating outdoor activities, there is something for everyone. For those looking to explore more, consider checking out other towns nearby, such as Saratoga or Queensbury, which offer their own unique highlights.
As you leave Sleepy Hollow, the memories of its enchanting landscapes, charming festivals, and warm community will linger in your mind. This unique town invites you to return and discover even more of its hidden gems and stories.