35 Things To Do in Sleepy Hollow

Nestled in the heart of the Hudson Valley, Sleepy Hollow, New York, beckons visitors with its rich blend of history and charm. Known for its captivating legends and scenic beauty, this destination offers an enticing escape for travelers seeking adventure and relaxation.

Discovering what to do in Sleepy Hollow reveals a delightful mix of cultural landmarks, natural wonders, and seasonal festivities that capture the spirit of this enchanting village. Whether you’re drawn by the tales of the Headless Horseman or the chance to explore the tranquil landscape, Sleepy Hollow promises a memorable experience for everyone who visits.

Headless Horseman Bridge

Our Rating: 8.5/10

The Headless Horseman Bridge is a must-see. This historic site, steeped in Washington Irving’s legendary tale, offers an intriguing mix of beauty and eerie charm. Visitors can stand at the location marked by a plaque along Highway 9, adding a sense of history and excitement.

In the cemetery, a charming wooden replica of the bridge awaits. It’s a perfect spot to snap photos, surrounded by the tranquil yet haunting landscape. The walk to this bridge provides a peaceful experience, inviting visitors to immerse themselves in the town’s spooky lore.

Sleepy Hollow Cemetery

Our Rating: 8.5/10

Sleepy Hollow Cemetery is a journey through history and nature. Visitors can explore its 90 acres, home to famous figures like Washington Irving and Andrew Carnegie. It offers a peaceful, park-like setting with winding paths.

Guided tours, available in the afternoon and evening, provide stories of the notable individuals resting here. With its rich history and serene beauty, this cemetery is a captivating destination for those visiting Sleepy Hollow.

Philipsburg Manor

Our Rating: 8.6/10

Philipsburg Manor invites visitors to return to 1750, exploring the rich history of a colonial farming and trading center. This history museum lets people experience the life of the 23 enslaved individuals who once lived there.

Visitors can wander through the historic core to see the gristmill in action or stroll around the scenic five-acre site. The history here feels vibrant and alive, with guides in period costumes and engaging storytelling. Special programs and activities can captivate kids and adults alike, making it a perfect stop for families and history enthusiasts.

Kykuit, the Rockefeller Estate

Our Rating: 8.5/10

Kykuit, the Rockefeller Estate, is an architectural gem. This Gilded Age mansion offers breathtaking views of the Hudson Valley and showcases the grandeur of American history. Visitors can explore its beautifully manicured gardens and striking sculptures. Guided tours provide glimpses into the Rockefellers’ lavish lifestyle.

Inside, the home boasts an impressive collection of art and antique furnishings. The estate’s history is as fascinating as its elegant design, making it a must-see for history buffs and art lovers. Tours vary in length, offering a range of experiences from classic highlights to in-depth exploration. If you’re in the area, take advantage of this splendid estate.

Old Dutch Church

Our Rating: 8.5/10

The Old Dutch Church is a must-see destination steeped in history and mystery. Dating back to the late 17th century, its stone walls whisper tales of the past. Visitors can wander through the adjoining burying ground where ancient gravestones stand.

The church’s simple yet elegant interior brings a sense of peace. Visitors can attend events or enjoy the serene atmosphere while reflecting on its history. This iconic landmark also significantly influenced Washington Irving’s famous tale, “The Legend of Sleepy Hollow.” A visit to the Old Dutch Church offers a unique peek into early American history wrapped in the charm of Sleepy Hollow.

Sleepy Hollow Lighthouse

Our Rating: 8.5/10

Sleepy Hollow Lighthouse is an iconic beacon by the Hudson River, offering breathtaking views of the shimmering waters and surrounding landscapes. Visitors can stroll along the nearby Scenic Hudson Riverwalk, enjoying the peaceful ambiance and panoramic vistas that change with the light and seasons.

Photography enthusiasts will find unique angles to capture, with the lighthouse providing a stunning focal point. Picnicking on the grassy areas nearby allows for a relaxing time with family or friends while soaking in the tranquil setting. As the sun sets, the light from the lighthouse dances on the water, creating a mesmerizing scene perfect for those who appreciate simple yet profound beauty.

Rockefeller State Park Preserve

Our Rating: 8.7/10

The Rockefeller State Park Preserve, gifted by the Rockefeller family, welcomes visitors with enchanting landscapes. This expansive park spans over 1,700 acres. It’s a paradise for outdoor enthusiasts, boasting over 45 miles of well-maintained carriage trails. Hikers and runners find these paths perfect for connecting with nature.

Bird watchers can delight in spotting various local species, while those with a fishing license can cast lines into the serene waters. Horseback riders and carriage drivers, too, will find the trails inviting and peaceful. Whether picnicking in a sunny meadow or simply enjoying the fresh air, there’s something here for everyone to savor.

Sleepy Coffee Too

Our Rating: 8.5/10

Sleepy Coffee Too is a charming spot where kindness and community come together. This non-profit café offers a warm welcome and serves inclusive vibes with every cup.

Visitors can enjoy their coffee while learning about the café’s inspiring mission to support individuals with differing abilities. It’s not just about coffee; it’s about connection.

Legend of Sleepy Hollow Statue

Our Rating: 8.5/10

Standing tall and mysterious, the Legend of Sleepy Hollow Statue is in the heart of Sleepy Hollow. This captivating sculpture captures the thrilling chase of the Headless Horseman, an iconic figure from Washington Irving’s famous tale. Visitors can admire the detailed artistry of the statue, which brings the legend to life with remarkable realism.

The area around the statue is perfect for a stroll, providing opportunities for photography and experiencing Sleepy Hollow’s charming ambiance. Perfect for fans of folklore and history, the Legend of Sleepy Hollow Statue invites you to step back into an era of mystery and imagination.

Patriots Park

Our Rating: 8.6/10

Nestled between Tarrytown and Sleepy Hollow, Patriots Park is a captivating green space with deep historical roots. Visitors can stroll along scenic paths, enjoying views of the flowing stream, which adds a peaceful touch to the park’s atmosphere.

Families love the playground, where laughter and joy fill the air. Couples often take romantic walks over the charming bridge, admiring the tranquil waters below. History buffs can explore monuments commemorating pivotal Revolutionary War events, making it a must-visit spot for anyone exploring Sleepy Hollow’s rich history.

Bridge View Tavern

Our Rating: 9.0/10

Bridge View Tavern is a must-visit for those exploring this charming village. The tavern is known for its impressive selection of craft beers, offering both draught and canned options. Each visit brings the possibility of discovering a new favorite brew.

Beyond drinks, the tavern’s menu promises excitement with house-smoked BBQ and game burgers. Diners can savor an array of regional American dishes and ethnic favorites. With a cozy atmosphere and stunning views of the Tappan Zee Bridge, time spent here feels like a mini-vacation from city life.

Horsefeathers Restaurant

Our Rating: 8.5/10

Horsefeathers Restaurant offers a warm and inviting atmosphere, perfect for travelers exploring the historic Sleepy Hollow area. Nestled along Route 9, this charming spot is not just a place to dine but a local legend, celebrating the vibrant folklore of the region.

Visitors can indulge in classic and New American cuisine, with a menu that satisfies various tastes. The décor is a delightful mix of rich history, creating a cozy backdrop for a memorable dining experience. It is a must-visit for anyone enjoying the unique charm of Sleepy Hollow’s local culture.

Warner Library

Our Rating: 8.5/10

Warner Library is a beacon of community spirit in Tarrytown and Sleepy Hollow. This historic library offers more than just books. Visitors can explore its vast collection or attend engaging programs that cater to all ages.

You’ll find cozy reading corners perfect for losing yourself in a story. The library also provides tech help for those needing assistance with gadgets or research projects. Warner Library is a vibrant hub. In addition to its collection, it hosts events and meetings. Something always happens here, whether it’s a book club or a local history session.

TaSH Farmers Market

Our Rating: 8.5/10

The TaSH Farmers Market is a delightful gem in the charming Patriots Park. Every Saturday, from late spring to late fall, the market offers a lively atmosphere filled with over 50 local vendors. Visitors wander through stalls with fresh produce, meats, artisanal bread, and vibrant flowers. Talented local musicians perform live, adding to the market’s vibrant vibe.

Families and friends gather on the grassy lawn, sharing delicious treats and enjoying the festive mood. Kids dance to the lively tunes while various educational programs and fun activities keep them entertained.

J.P. Doyle’s Restaurant & Public House

Our Rating: 8.9/10

J.P. Doyle’s Restaurant & Public House offers an inviting atmosphere to visitors in Sleepy Hollow. It’s renowned for its delicious dishes, including famous BBQ ribs and the Horseman Burger, which promises a flavorful experience.

The restaurant’s warm interior and friendly staff make it an ideal spot to enjoy a relaxed meal. Whether dining solo or with a group, the lively vibe and savory menu ensure a delightful visit.

Washington Irving’s Sunnyside

Our Rating: 8.5/10

Washington Irving’s Sunnyside is a delightful escape into the past. This charming estate, nestled beside the Hudson River, invites visitors into the world of the famed author of “The Legend of Sleepy Hollow.” The house, designed by Irving himself, blends architectural styles and offers a glimpse into 19th-century life.

Guests can explore the lush grounds filled with winding paths and serene views. Guided tours bring Irving’s story to life, with storytellers dressed in period attire sharing tales and insights. The enchanting atmosphere makes it a must-visit for those seeking history and nature in one beautiful setting.

Stone Barns Center for Food & Agriculture

Our Rating: 8.5/10

Nestled in the picturesque Pocantico Hills, the Stone Barns Center invites visitors to immerse themselves in a world of sustainable agriculture and innovation. This vibrant farm and education center offers more than just a taste of rural charm. Guests can explore the grounds, soak in the scenic beauty, and learn about the roots of local food production.

Visitors can take self-guided tours and attend engaging programs to educate and inspire. Reservations enhance the experience, ensuring a unique and personalized visit. Stone Barns connects the past with the present, honoring the rich farming heritage of the native peoples who first nurtured this land.

Tarrytown Waterfront

Our Rating: 8.3/10

The Tarrytown Waterfront is a captivating destination for those who love being near the water. With stunning views of the Hudson River and the majestic Tappan Zee Bridge, it offers a serene escape for visitors. A stroll along the scenic riverfront path is perfect for unwinding after a busy day.

Boating enthusiasts can enjoy kayaking or paddleboarding on the calm waters. It’s a refreshing way to connect with nature and enjoy the tranquility of the river. The waterfront park is also an excellent spot for picnics. Plenty of green space and shady trees make it a great place to relax, enjoy lunch, and watch the boats glide.

Barnhart Park

Our Rating: 7.8/10

Barnhart Park is a beautiful spot for families and nature lovers. With its newly renovated facilities, the park offers a range of activities for everyone. Children can laugh and play on the playground equipped with modern play structures.

Sports enthusiasts will appreciate the basketball and volleyball courts, where friendly matches often occur. Benches are scattered throughout the park for those seeking a more restful experience. Relax and soak in the peaceful surroundings. The park is also an excellent spot for a casual stroll or a picnic, making it easy to unwind and enjoy nature’s beauty.

Santorini Greek Restaurant

Our Rating: 8.4/10

In the heart of Sleepy Hollow lies Santorini Greek Restaurant, a family-owned gem that offers authentic Greek flavors. Guests are greeted with the warm aroma of Mediterranean spices and can indulge in various traditional dishes.

The restaurant is known for its homemade soups, fresh salads, and various cold and hot appetizers. The seafood, brought in daily, adds a fresh touch to any meal, making it a delight for fish lovers. Located just minutes from the Sleepy Hollow Lighthouse, it’s the perfect stop after a day of exploring local sights. Santorini promises a genuine taste of Greece in a cozy setting.

Pierson Park

Our Rating: 8.5/10

Pierson Park is a delightful escape on the Hudson River in Tarrytown, New York. Visitors can stroll along the park’s scenic Hudson Riverwalk, a path adorned with native plants. They can also rest and take in the beauty of the river from one of the benches scattered along the walk.

Families and friends gather for picnics with stunning river views as a backdrop. There’s plenty of space for kids to play and explore the playground. The park is perfect for a relaxing day, with opportunities to enjoy the fresh air and watch boats pass by on the Hudson.

Horan’s Landing

Our Rating: 8.5/10

Horan’s Landing captivates visitors with its scenic Hudson Riverfront charm. The park boasts a lush grassy area perfect for picnics and leisurely afternoons. It provides a stunning backdrop for relaxation or playful moments. The small beach at the park is a hotspot for launching kayaks and paddleboards, making it ideal for water sports enthusiasts eager to explore the river.

Though swimming is not permitted, the water activities are unforgettable. Music lovers will relish the summer concerts held here. Regional bands play while the sun sets over the Hudson River, offering a magical experience. Horan’s Landing is not just a park; it’s a vibrant and lively gathering spot.

Welcome to Sleepy Hollow Sign

Our Rating: 8.3/10

Visitors feel excitement and mystery in front of the “Welcome to Sleepy Hollow” sign. This iconic sign marks the gateway into a village rich with history and legend. It prompts many to snap a photo, capturing the start of their Sleepy Hollow adventure.

Surrounded by the village’s charm, the sign is perfect for photo enthusiasts seeking the perfect backdrop. As travelers arrive, they sense the echoes of stories that Sleepy Hollow is famous for. The sign sets the stage for adventures and explorations that await within this legendary place.

Kingsland Point Park

Our Rating: 8.5/10

Kingsland Point Park is a hidden gem in Sleepy Hollow, New York. This 18-acre riverfront park offers stunning views of the Hudson River and the iconic Tappan Zee Bridge. Visitors can enjoy strolls along scenic pathways or set up a picnic near the water.

Families will love the playgrounds that provide kids with a fun and safe space. Sports enthusiasts can head over to the soccer and lacrosse fields. If you’re feeling adventurous, try the kayak tours to get a unique perspective on the area. Don’t miss the chance to visit the historic Sleepy Hollow Lighthouse. Kingsland Point Park has something for everyone to enjoy, whether you’re there for relaxation or excitement.

Canfin Gallery

Our Rating: 8.3/10

Art lovers must stop by Canfin Gallery. This cozy and chic art space features contemporary artwork from emerging and established artists. Visitors can soak in vibrant paintings, unique sculptures, and captivating photographs.

The gallery provides an intimate setting for guests to wander and experience art up close. Exhibitions change periodically, so there is always something new and exciting to discover. This makes each visit to the Canfin Gallery a fresh, inspiring experience.

St. Teresa of Avila Church

Our Rating: 8.5/10

St. Teresa of Avila Church is more than just a place of worship; it’s a community cornerstone. This charming church, located on Beekman Avenue, offers visitors a serene escape from the hustle and bustle of daily life.

Visitors can admire the beautiful architecture and participate in various community events. The church regularly holds engaging “listening sessions,” fostering a sense of togetherness among locals and travelers. Whether attending a service or exploring the historic surroundings, the church provides a peaceful retreat in a picturesque setting.

Hudson Valley Writers’ Center

Our Rating: 8.5/10

The Hudson Valley Writers’ Center is a creative haven for literature lovers. Located in a historic building at the Philipse Manor Station, this enchanting place invites writers and readers to explore new worlds of words.

Visitors can attend unique classes that nurture writing skills for all levels. Workshops cover various genres, providing a platform for budding and seasoned authors alike. The center also features a versatile performance space where storytelling and poetry readings create a vibrant literary atmosphere.

Hudson Farmer & The Fish Restaurant

Our Rating: 8.6/10

Hudson Farmer & The Fish offers a delicious journey through fresh ingredients and scenic views. Located by the Hudson River, visitors can savor seafood and farm-fresh flavors while enjoying outdoor seating with a waterfront sight.

Dinosaurs in the shape of steaks and sweet potatoes are just the beginning of their creative dishes. Enjoy dining in a relaxed atmosphere connecting you to land and river. The restaurant proudly showcases products from their northern farm, giving each meal a genuine touch of freshness. A visit isn’t complete without soaking in the riverside vibe, making it a perfect stop after exploring the beautiful Riverwalk in Sleepy Hollow.

Rockefeller Archives Center

Our Rating: 8.5/10

The Rockefeller Archives Center is perfect for history lovers in Sleepy Hollow. Visitors can explore a vast collection of documents that provide a window into the Rockefeller family’s influence on American history. The center is not just for research; it’s a journey into the past that captivates every visitor.

The weekday reading room is open, offering a quiet and reflective space. Researchers can delve into archives on philanthropy, public policy, and more. This is a unique opportunity to gain insights into the Rockefellers’ impact on education and environmental conservation.

Coffee Labs Roasters Inc.

Our Rating: 8.5/10

Coffee Labs Roasters Inc. is a haven for coffee lovers. Focusing on Farmer Direct beans, this cozy café promises an aromatic and flavorful experience. Visitors can enjoy the meticulous crafting of drinks by trained baristas who use various methods, such as pour-over and espresso. The engaging staff helps guests choose from various sustainable coffee options.

In addition to delightful beverages, a selection of local treats pairs perfectly with each cup. The warm atmosphere makes it an inviting spot to rest and recharge during a day of exploration.

Jazz Forum

Our Rating: 8.3/10

The Jazz Forum is a 90-seat club haven for jazz lovers. As Westchester County’s only dedicated jazz venue, it offers a cozy atmosphere where guests can enjoy live music. Every weekend, the space fills with the soulful sounds of jazz, featuring talented performers worldwide. Visitors can immerse themselves in the intimate vibe and clear sightlines that ensure every seat feels like the best one in the house.

With its warm mood and affordable ticket prices, the Jazz Forum promises an unforgettable musical escape. It’s an essential stop for anyone wanting to experience the vibrant culture of Sleepy Hollow.

Sleepy Hollow Bookshop

Our Rating: 8.5/10

Step into the charming Sleepy Hollow Bookshop, where the love of books and the joy of reading come alive. This inviting space is more than just a bookstore; it’s a hub of creativity and community. Every Tuesday morning, kids and parents can enjoy the SHAC Bookshop Shindig. It’s filled with live music and fun toys, bringing laughter and joy.

Visit on Thursdays for Storytime, where children of all ages can dive into delightful tales. The welcoming atmosphere of the bookshop makes it a special place to unwind and explore new worlds.

Sleepy Hollow Riverfront Community Mural

Our Rating: 8.5/10

Standing proudly along Sleepy Hollow’s waterfront, the community mural is a vibrant tapestry of color and creativity. Spanning 520 feet, this mural was brought to life by residents who joined forces to transform a barren concrete wall into a kaleidoscope of artistic expression. Adventurers, art lovers, and curious visitors can explore this colorful masterpiece.

Walking beside the mural, they can admire each section’s intricate designs and stories. The community’s spirit shines through as every brushstroke tells a tale of unity and transformation. It’s not just an artistic feast for the eyes; the mural provides a lively backdrop for photography enthusiasts seeking that perfect shot and an inspiring reminder of what can be achieved through collaborative creativity.

Riverstone Wellness Center

Our Rating: 8.5/10

Riverstone Wellness Center is a place where relaxation meets revitalization. This oasis offers an array of holistic treatments designed to rejuvenate the body and mind. Visitors can indulge in soothing massages that melt away stress or join yoga sessions surrounded by calming nature views.

The center provides wellness workshops that explore meditation, mindfulness, and healthy living. These sessions create a peaceful environment, perfect for those seeking a break from the hustle and bustle. The serene atmosphere enhances the experience, inviting guests to unwind completely.

Tarrytown House Estate on The Hudson

Our Rating: 8.5/10

Nestled gracefully on the bluffs of the Hudson River, Tarrytown House Estate offers visitors a charming escape into elegance and history. Its lush gardens and stunning views create a perfect backdrop for strolls.

Guests can indulge in luxurious dinners or host grand celebrations with impeccable service. Whether exploring the estate’s historical architecture or enjoying a cozy evening by the fireplace, there is no shortage of captivating experiences at the Tarrytown House Estate. It’s an inviting haven that embodies the beauty and allure of the Hudson Valley.

As you explore the enchanting village of Sleepy Hollow, each adventure promises its unique story, wrapped in rich history and folklore. Whether seeking thrills, cultural enrichment, or peaceful retreats, Sleepy Hollow offers a delightful escape into a world where legends come alive.