14 Top Things to Do in Sleepy Hollow, NY

Author Meagan Drillinger grew up in southern Westchester County, where Sleepy Hollow is located.

Sleepy Hollow, New York has a reputation that certainly precedes it. Immortalized in the pages of literature by Washington Irving in his tale of The Legend of Sleepy Hallow, the historic Hudson River community has been drawing visitors for centuries.

Today the village of Sleepy Hollow, NY sits perched on the banks of the Hudson River, affording it stunning views, a historic downtown packed with things to do, and a charming family vibe that is central to so many small towns in the Hudson Valley.

But Sleepy Hollow is so much more than the setting for Irving's eerie tale. Its history is rooted in Native American tribes and eventually European farmers. The Rockefeller family, New York State royalty, essentially, made the village one of their beloved homes, as well. Much of the surrounding area is protected land, offering visitors and locals ample opportunity to explore the great outdoors in the hills that rise from the banks of the Hudson River.

Stroll Beekman Avenue to explore the shops, galleries, restaurants, and coffee shops, or browse the stalls at the weekly farmers market. Whether it's history, art, culture, or the outdoors, Sleepy Hollow is one of those iconic New York state small towns you won't want to miss.

Discover the best places to visit with our list of the top things to do in Sleepy Hollow, NY.

Tour Kykuit Estate

The Rockefeller family is as close as one can get to New York royalty. John D. Rockefeller, founder of Standard Oil, made his millions in the petroleum industry in the 19th century, and the family has left its mark all over New York City and the Hudson Valley. Sleepy Hollow is no exception, home to Kykuit, the Rockefeller Estate.

This colonial-style mansion was built in 1913 by John D. Rockefeller up in the hills overlooking Sleepy Hollow and Tarrytown. It rises six stories, its façade and stone archways draped in ivy and the grounds beautifully manicured.

The interiors are beautiful, as well. Believe it or not, the basement of the mansion houses the Rockefeller's impressive private collection of modern art, including Picassos, Calders, Henry Moore, and Andy Warhol. Today, the mansion is still owned by the Rockefeller family, but is open to the public.

Address: 381 N. Broadway, Sleepy Hollow, New York

Read More: Top Things to Do in Upstate New York

Feel a Chill at the Sleepy Hollow Cemetery

Sleepy Hollow is brimming with so much history, both factual and fictional. Many of its historic roots can be found right at the Sleepy Hollow Cemetery, one of its most popular places to visit. Wander the grave sites to discover many of Sleepy Hollow's notable figures, from William Rockefeller to Washington Irving, Walter Chrysler, and Andrew Carnegie.

The cemetery is listed both on the New York State and the National Registers of Historic Places. It is known for its stunning views of the Hudson River, beautiful rolling hills, sculptures, and impressive mausoleums. The entire cemetery has 85 acres and was opened in 1849.

The Pocantico River runs through the cemetery and adds to the beauty of the grounds. Visitors can purchase tickets to tours of the cemetery, too, whether it's the Classic Evening Lantern Tour that visits the graves of the most impressive residents or The Legend of Sleepy Hollow tour, which focuses specifically on Irving and his impact.

Address: 540 N. Broadway, Sleepy Hollow, New York

Step Back in Time at Philipsburg Manor

If you've ever wondered what New York State looked like in the mid-18th century, Philipsburg Manor is the place to find out.

The property, once occupied by European farmers under the Philipse name, today transports visitors back to the year 1750, when the manor was a bustling grist mill. The Philipse family property spanned 52,000 acres that included a mill, farm, and manor house that overlooked the Pocantico River.

But the Manor was known for a dark side, as well, as it was home to 23 slaves of African descent. Today the Manor serves as a living museum to bring awareness to American slavery, as well as farm life in the 18th century.

Visitors can tour the exterior, as well as the interior of the manor, to discover period artifacts and reproductions of the time period. Staff on-site are in costume and tell the stories of the Philipse family who owned the manor.

Address: 381 N. Broadway, Sleepy Hollow, New York

Tour the Old Dutch Church

Many know the iconic Washington Irving tale, The Legend of Sleepy Hollow, but few know that the tale is based on an actual place. The Sleepy Hollow of Irving's time is very much real and was the inspiration for his haunted tale of the Headless Horseman. The actual site of inspiration was the Old Dutch Church, which just so happens to be the oldest existing church in New York.

The Old Dutch Church of Sleepy Hollow is actually the church on the site of the Sleepy Hollow Cemetery. It was founded in 1685 and is still in operation to this day. In the 1960s, the church was named a National Historic Landmark.

The church and its grounds attract thousands of visitors every fall who come to see the spooky site in person and to take part in the seasonal events that highlight the town's iconic legend.

Address: 430 Broadway, Sleepy Hollow, New York

Explore Rockefeller State Park Preserve

The Rockefeller State Park Preserve just north of Sleepy Hollow is the former Pocantico Hills and Rockwood Hall county estates of the famous John D. Rockefeller. This 1771-acre preserve was donated to New York State in order to preserve the natural beauty and wildlife for the future.

Today visitors can wander the 45 miles of scenic carriage roads past Swan Lake, the Pocantico River, over stone bridges, and out to scenic overlooks. Along the way, it's common to spot the many species of wildlife from the 202 different species of birds to amphibians, fish, monarch butterflies, and more.

The historic Rockwood Hall estate still stands in a beautiful section of the preserve overlooking the Hudson River and the Palisade Cliffs on the other side. William Rockefeller lived at Rockwood Hall from 1886 to 1922 in the 202-room mansion.

Address: 125 Phelps Way, Pleasantville, New York

Read More: Best National & State Parks in New York

Fill Your Baskets at the Farmers Market

The Tarrytown-Sleepy Hollow Farmers Market (TaSH) is a vital part of this Hudson River community. The market is open every Saturday in Patriots Park, which sits on the border between Sleepy Hollow and Tarrytown. (Tarrytown and Sleepy Hollow are right next door to each other, and one blends seamlessly into the other).

Every Saturday since 2015, locals and visitors line up for fresh produce, breads, baked goods, meats, cheeses, artisanal prepared foods, and more. More than 30 vendors are out in full force across the park.

In addition to the kaleidoscope of colorful offerings, live entertainment is always on hand, from chef demonstrations and children's activities to art classes. During the holidays TaSH hosts its annual Tree Lighting Festival and holiday pop-up market, which is always a festive, sparkling occasion for residents and visitors.

Address: Patriots Park, Sleepy Hollow, New York

Read More: Top Things to Do in Tarrytown, NY

Get Spooked at the Headless Horseman Bridge

Washington Irving tells us in The Legend of Sleepy Hollow about a wooden bridge where the Headless Horseman was most frequently encountered. It turns out that the bridge is a real place in Sleepy Hollow. While the bridge itself is not the original that existed during Washington Irving's time, the location is similar, crossing the Pocantico River on the property of Sleepy Hollow Cemetery.

The modern bridge that exists is wide and uncovered, though the film adaptations of the legend often show a more romantic, spooky covered bridge. Today a historical sign indicates that the bridge that stands is in the exact spot as the legendary one, though this isn't exactly accurate. It's about a half-mile off.

According to the legend, hero Ichabod Crane is chased by the Headless Horseman through the woods, where he is finally caught at a wooden bridge over the Pocantico River. Here is where the Headless Horseman throws a pumpkin at Crane, and all that can be found in the morning are the remains of Crane's saddle and broken bits of pumpkin.

Tour Washington Irving's Sunnyside Home

Technically in Tarrytown, Sunnyside is the historic residence of author Washington Irving, who wrote The Legend of Sleepy Hollow while living there.

The building was designated a National Historic Landmark in the 1960s. It was originally part of the Manor of Philipsburg estate. In 1835, Irving purchased the then-two-room Dutch stone house that overlooks the Hudson River. From here, he added Tudor-style chimneys, gables, Gothic windows, and a Spanish tower. He also had a hand in landscaping the grounds.

Today, the house and grounds have been returned to how they would have looked in the 1850s, with many of the original furnishings. Tourists visit Sunnyside to learn all about the life of Washington Irving, and the folklore surrounding him and the home. But keep your wits about you, as the mansion is rumored to be haunted. It's a very popular spot for visitors looking for goosebumps on Halloween.

Address: 3 W. Sunnyside Lane, Irvington, New York

Visit the Sleepy Hollow Lighthouse

The Sleepy Hollow Lighthouse goes by a few other names (the Tarrytown Lighthouse and the Kingsland Point Lighthouse), but all refer to this historic landmark. The lighthouse was installed in 1883 and ever since has kept watch over the dangerous points along the east side of the Hudson River.

Back in the days when it housed light keepers, the lighthouse had five floors of living space, including a kitchen, dining, and living room, three bedrooms, a work room, and a small watchtower room at the top. The light of the lighthouse was originally a fixed red light, but was replaced in 1902 with a rotating, white light.

The lighthouse became automated in the 1950s but prior to that, it had a history of 12 lightkeepers and their families who lived within the tower.

The lighthouse became irrelevant in 1961 with the construction of the Tappan Zee Bridge. Today visitors can tour the lighthouse to learn its history, and grab photos from the best viewpoints along the Westchester RiverWalk.

Address: Tarrytown Light-Kingsland Point Path, Sleepy Hollow, New York

Spot Chagall and Matisse

Did you know that this small Hudson River town is one of the top spots to drink in art from Henri Matisse and Marc Chagall? With residents like the Rockefellers, it's no wonder this Westchester County community is blessed with world-class art.

Just below Kykuit is the Union Church of Pocantico Hills, which houses some stunning under-the-radar stained-glass works from Matisse and Chagall. Start with the rose window by Matisse, which happens to be the last work he completed before he died in 1954. The church has nine windows that were designed by Chagall, the most famous of which is the Good Samaritan window.

The works were commissioned by Nelson A. Rockefeller to commemorate his mother, Abby Rockefeller. Tickets are less than $10, and a tour is under half an hour.

Address: 555 Bedford Road, Tarrytown, New York

Indulge at Castle Hotel & Spa

The Hudson Valley has many charming hotels and spas, but few are as impressive as Castle Hotel & Spa. This stately stone manor exudes majestic elegance as it overlooks the Hudson River from one of the highest points in the region. The estate features 31 guest rooms and suites and is a member of Small Luxury Hotels of the World.

In addition to gorgeously appointed guest rooms and top-notch views, the hotel has a 24-hour health and fitness center, whirlpool, and manicured jogging paths. The hotel is renowned for its Equus restaurant, which has received Four Diamonds from AAA. The Sankara Spa is one of the best in the region, as well.

Visitors to Sleepy Hollow and the surrounding area can use Castle Hotel & Spa as the perfect home base from which to go sightseeing around Sleepy Hollow and visit other scenic tourist attractions along the Hudson River Valley.

Address: 400 Benedict Ave, Tarrytown, New York

Snap a Photo at the Headless Horseman Sculpture

While you're in town, you might as well overindulge in Headless Horseman lore with a stop at the Headless Horseman sculpture. Towering at 18 feet, and sitting across from Philipsburg Manor, this sculpture was created by artist Linda Perlmutter.

The sculpture depicts a Surrealist horseman in hot pursuit of an equally nightmarish Ichabod Crane. The steel structure was treated with a specific wash to allow it to oxidize to give off its burnt orange, Halloweenish coloring.

Be Mesmerized at the Annual Great Jack O'Lantern Blaze

Every Halloween, this part of Westchester County becomes the host to one of the largest events in the county. The Great Jack O'Lantern Blaze happens every Halloween night and quite literally sets the world aglow with thousands of blazing Jack O'Lanterns.

Just 15 minutes from Sleepy Hollow is the Hudson River town of Van Cortlandt Manor, where the festivities take place. More than 7,000 hand-carved pumpkins radiate warm, candle glows against the historic 18th-century buildings.

But the illuminated pathways and beautiful carvings are not the only events on All Hallow's Eve. Other festivities include the Museum of Pumpkin Art, the Pumpkin windmill, and the Pumpkin Planetarium. It is one of the best things to do in Sleepy Hollow in the fall to really help get you into the autumnal and Halloween spirit.

Read More: Best Drives to See Fall Foliage in New York

Marvel at the Armour-Stiner Octagon House

If you love unique architecture, then the Armour-Stiner Octagon House is a must. It's one of the only fully domed octagonal residences in the world, built after Donato Bramante's 1502 Tempietto in Rome.

The house is a private residence today, though you can book some tours in advance. Still, you can certainly stop by to snap a picture. It really is something fascinating to see. It was constructed in the 19th century by Joseph Stiner, a tea merchant from New York City.

The house was acquired by the National Trust for Historic Preservation in 1976 and was sold to a preservation architect in 1978. Today the house has been restored back to its 1872 origins, including its furnishings and décor.

Address: 45 W Clinton Ave, Irvington, New York