25 Amazing Things To Do In Sleepy Hollow, NY for 2024
Looking For The Best Things To Do in Sleepy Hollow, NY?
Not many people know this, but Sleepy Hollow, NY is more than just the setting for Washington Irving’s famous tale of the Headless Horseman.
We loved visiting this charming, quiet village on the Hudson River and its just a treasure trove of unique experiences waiting to be discovered. From historic sites and riveting ghost stories to breathtaking landscapes and quaint local culture, there’s no shortage of things to do in Sleepy Hollow, NY.
Let’s dive into the must-see attractions and hidden gems that make this village so enchanting and see why we fell in love with Sleepy Hollow, NY!
Why Visit Sleepy Hollow
Sleepy Hollow, NY may be most famous for its spooky legends and haunted past, but it actually has so much more to offer.
There are endless things to do in Sleepy Hollow, NY that make it the perfect destination for anyone looking for a unique and exciting vacation. From exploring the historic Philipsburg Manor, to hiking through the beautiful Rockefeller State Park Preserve, Sleepy Hollow offers something for everyone.
Visitors can also take a stroll through the Sleepy Hollow Cemetery, where they can visit the final resting place of famous figures such as Washington Irving and Andrew Carnegie. Whether you’re interested in history, culture, or the supernatural, Sleepy Hollow, NY has it all.
1. Visit The Sleepy Hollow Cemetery
540 N Broadway
One of the first places I visited was the Sleepy Hollow Cemetery.
This historic and picturesque site is located in the heart of the village and is the final resting place of many notable figures, including Washington Irving, the author of “The Legend of Sleepy Hollow,” and Andrew Carnegie, the famous philanthropist.
But this cemetery is much more than just a burial ground. It’s also a beautiful park with winding paths, towering trees, and stunning views of the Hudson River. Visitors can take guided tours to learn about the cemetery’s fascinating history, or explore on their own and discover hidden gems like the beautiful stained glass window at the Memorial Chapel.
The cemetery also conducts many tours as it can be difficult to navigate such a large place on your own. Their Classic Daytime and Evening Tour discuss those who have been buried on site and dive into interesting information like cemetery symbolism.
Their Murder and Mayham Tour is offered during October and November on selected days, and discussing some of the more disturbing stories of those who have been buried there.
➡️ Book Your Tour On Their Site! ⬅️
The cemetery is open every day from 8:00 AM to 4:30 PM on Monday through Friday and from 8:30 AM to 4:30 PM on Saturday and Sunday.
The cemetery itself is a hauntingly beautiful place, with winding paths and towering trees that create an eerie yet serene atmosphere. It’s a must-visit for anyone interested in history or literature.
2. Take A Guided Ghost Tour
While many would think to go right to the famous cemetery for a ghost tour, it’s actually the Tarrytown Music Hall that does actual paranormal investigations!
On selected nights throughout the month of October, you can explore the theatre with paranormal experts and learn about the history of this building that have seen the likes of grand balls and live performances. Many famous millionaires like the Vanderbilts and Rockefellers would be present at such events.
➡️ Check Out Their Schedule and Book A Tour Here! ⬅️
3. The Old Dutch Church
430 North Broadway
The Old Dutch Church is another historic gem in Sleepy Hollow. Built in the late 1600s, it’s one of the oldest churches in New York and its churchyard are depicted in Washington Irving’s short novel “The Legend of Sleepy Hollow.”
The church’s 2.5-acre burial yard is the rumored home of the headless horseman, as well as the last resting place of several locals who might have served as models for figures such as Katrina Van Tassel, Brom Bones, and others in the legendary tale.
Walking through its ancient doors, I felt transported back in time. The church’s quaint charm and historical significance make it a fascinating stop for any visitor.
4. Discover Philipsburg Manor
381 North Broadway
Stepping into Philipsburg Manor felt like stepping back into Colonial America. A restored 18th-century farm and mill, this historic site offers an immersive experience with costumed staff who bring the past to life.
I spent hours exploring the manor and its grounds, learning about the daily lives of the people who lived and worked there. It’s a fantastic place to get a sense of early American history.
5. Headless Horseman Bridge
The wooden bridge Irving would have known during his lifetime is long gone, which shouldn’t come as a surprise. The so-called Headless Horseman that exists in most people’s minds because of movies and TV shows has gone through various incarnations since Irving’s time, but none of them actually still exist.
While this is one of the most well-known things to do in Sleepy Hollow, New York, finding the actual bridge versus a picturesque bridge can be tricky for some people.
If you want the exact spot and bridge where the Headless Horseman threw a pumpkin at Ichabod Crane’s head over the Pocantico River, a sleek bridge is situated close to Sleepy Hollow Cemetery and the Old Dutch Reformed Church.
But if the actual bridge won’t do, the tourist information office advises using the rustic Cemetery Bridge as a substitute for more aesthetic photos.
6. Washington Irving’s Sunnyside Estate
3 W Sunnyside Lane, Irvington, NY
If the famous legend is what brought you to Sleepy Hollow in the first place, then you need to stop by the famed author’s estate.
For many years, visitors have been enchanted by Washington Irving’s beloved Sunnyside, which is tucked away on the banks of the Hudson River. Today’s you can learn about Washington Irving’s colorful history and how he became the country’s first well-known author abroad.
The estate also hosts some great seasonal events during the autumn months such as live readings of Irving’s famous legend, and even a “bewitching” tea party.
➡️ Check out their Events Guide here! ⬅️
7. Visit the Great Jack’O Lantern Blaze
525 S Riverside, Croton-on-Hudson
September 13th – November 17th, 2024
An amazing event held at the Van Cortlandt Manor is the Great Jack O’Lantern Blaze, an outdoor display of thousands of carved pumpkins, depicting iconic scenes from literature, pop culture, and nature.
Discover a stunning display of more than 7,000 lit jack-o-lanterns each hand carved as you meander through an 18th-century countryside.
This one-of-a-kind event, complete with synchronized lights and a unique music, should not be missed!
8. Find The Headless Horseman Sculpture
362 North Broadway (Approximate)
One of Sleepy Hollow’s most popular attractions is the statue of the Headless Horseman.
We found this 18-foot-tall sculpture of the Headless Horseman and Ichabod Crane situated in the Route 9 median between the Philipsburg Manor renovation and the Old Dutch Church.
The bridge where the Horseman would have thrown his pumpkin at Ichabod in Washington Irving’s “The Legend of Sleepy Hollow” is a short distance away from this location.
9. Shopping In Sleepy Hollow
How can you say you’ve been to the famed Sleepy Hollow and not pick up a little something for yourself? You know, as proof you’ve been there!
There are many fun souvenir shops, places to go for books and antiques, and local farmer’s markets. Many of the locations you can visit also have giftshops.
🛍️Bella’s Boutique – 35 North Broadway, Tarrytown, NY
🛍️Sleepy Hollow Bookshop – 95 Beekman Avenue, Sleepy Hollow, NY
🛍️Pretty Funny Vintage – 80 S Broadway, Tarrytown, NY
🛍️Trilogy Consignment – 54 Main St. Tarrytown NY
10. The TaSH (Tarrytown and Sleepy Hollow Farmer’s Market)
Something you won’t want to miss to do in Sleepy Hollow, NY, is the TaSH!
This farmer’s market in Tarrytown and Sleepy Hollow is the perfect place to spend a day. With live music, fresh produce, and unique artisanal goods, you’ll be able to immerse yourself in the town’s vibrant community.
Take a stroll by the Hudson River and admire the scenery while sampling some of the market’s delicious treats. The vendors at TaSH are among the most passionate purveyors of local food and drink, so you’re sure to find something that’ll tantalize your taste buds.
11. Check Out Haunted Hayrides and Scare Mazes
Go on a haunted house adventure at The Horsemen: Terror Lies in Chaos produced by Psycho Clan.
This latest horror production is a bizarre fever dream that takes place in a nightmare as the Four Horsemen of the Apocalypse approach. You are the one who must locate Chaos, the headless fifth horseman, and kill him before he kills us all in order to avert the end of the world!
Then you’ll want to check out the Sleepy Hollow’s annual Haunted Hayride!
Down Sleepy Hollow’s downtown’s well-lit streets, everything appears to be in order. Suddenly, you realize that you are exactly following Ichabod Crane’s escape from the Headless Horseman by traveling past the Old Dutch Church on the Albany Post Road. Do you have what it takes to go on Ichabod’s journey?
12. Hike Along The Hudson River
We enjoyed this beautiful hike along the Hudson River at Rockwood Hall State Park, a scenic spot with woods, meadows, and the foundation of a historic mansion.
This circular trek travels through carriage lanes that once led to William Rockefeller’s, John D. Rockefeller’s brother, summer estate known as Rockwood Hall and provide serene inclines and sweeping views of the Hudson River.
Although the mansion is gone, the foundations are still there, and the carriage roads built by the Rockefeller family allow visitors to have a pleasant stroll across the grounds while taking in the expansive vistas of the Hudson River.
13. Kykuit
381 N Broadway, Sleepy Hollow, NY
Visiting Kykuit, the Rockefeller Estate, felt like stepping into a different era. The opulence and grandeur of the mansion and gardens were awe-inspiring. I was struck by the attention to detail in every aspect of the estate, from the architecture to the meticulously maintained grounds.
The guided tour provided fascinating insights into the history of the Rockefeller family and their impact on the region. The art collection, featuring works by renowned artists, was a highlight of the tour. It’s a must-visit for anyone interested in history and art.
Walking through the gardens, I couldn’t help but marvel at the beauty and tranquility of the surroundings. The views of the Hudson River from the estate are simply breathtaking, making it a perfect spot for photography enthusiasts.
14. Armour-Stiner Octagon House
One of the most strikingly distinctive houses in New York is the Armour-Stiner (Octagon) House.
It is both the only house constructed in the shape of an old classical temple and the only known completely domed octagonal dwelling. During the 1860s, businessman Paul J. Armour of New York City constructed the Octagon House.
Joseph Stiner, a well-known tea dealer in New York City, bought the residence in 1872. He made changes that led to the current distinctive structure, such as the verandah and dome, with intentions of using the residence as a summer getaway.
The manor offers a variety of tours, including a Myths and Mysteries tour as the home owners themselves tell tales of their experiences in the possibly haunted home.
Currently, the Octagon House is a private residence Please only come during a booked tour in order to respect the owner’s privacy!
➡️ Check Out Their Site So You Can Book A Tour! ⬅️
15. The Union Church of Pocantico Hills
555 Bedford Road, Pocantico Hills, NY
Visit the Union Church of Pocantico Hills so you can see the windows designed by stained-glass artist Henri Matisse and Marc Chagall
Nestled away in the hills above Sleepy Hollow, the Protestant non-denominational congregation was established in 1915. Its current structure was built in 1922 on property that John D. Rockefeller, Sr. donated.
The Rockefeller family commissioned stained glass windows by European artists to beautify this inconspicuous country chapel. The Rose Window, the final commissioned piece by Henri Matisse, and nine windows by Marc Chagall are definitely a sight to behold!
16. Apple Picking At Local Farms
Among all the options of things to do in Sleepy Hollow, NY, there’s one activity that stands out as a must-do: apple picking at local farms.
As fall approaches, the orchards become a vibrant tapestry of yellows, reds, and oranges, and the air is filled with the scent of fresh apples. Picking your own fruit is a unique experience that offers the chance to connect with nature, get some exercise, and support local businesses.
Plus, you can enjoy the fruits of your labor by baking pies, making cider, or simply biting into a juicy, crunchy apple. Or, you can enjoy the tasty treats provided by the storefronts located right on the farm! Some even have bakeries or kitchen with a full menu!
So, if you’re looking to experience the best of Sleepy Hollow, don’t miss out on the seasonal joy of apple picking.
🍎 Wilkens Fruit and Fir Farm – 1335 White Hill Rd, Yorktown Heights, NY
🍎 Salinger’s Orchard – 230 Guinea Rd, Brewster, NY
🍎 Harvest Moon Farm and Orchard – 130 Hardscrabble Road, North Salem, NY
🍎 Outhouse Orchards – 139 Hardscrabble Road, North Salem, NY
🍎 The Orchards of Concklin – 2 South Mountain Road Pomona, NY
17. Take A Tour of Lyndhurst
635 South Broadway, Tarrytown, NY
I just love going on tours of beautiful old homes and mansions and Lyndhurst, the Gothic Revival mansion, was like stepping into a classic novel. The architecture and the lush grounds make for a beautiful day out. The mansion is a stunning example of Gothic Revival architecture, with its intricate details and grand design.
The guided tour provided fascinating insights into the history of the mansion and its former residents. The interior of the mansion is equally impressive, with beautifully decorated rooms that showcase the opulence of the era. It’s a must-visit for anyone with an appreciation for history and architecture.
The grounds of Lyndhurst are equally enchanting, with well-maintained gardens and scenic views of the Hudson River. It’s a perfect spot for a leisurely stroll or a picnic with family and friends.
➡️ Check Their Site For Events! ⬅️
18. Sleepy Hollow Street Fair
Saturday October 5, 2024 10:00 AM – 4:00 PM
If the first weekend of October falls during your trip, be sure to swing by the Sleepy Hollow Street Fair where you can discover food, music, local shops, arts & crafts, as well as Halloween and holiday merchandise!
I loved exploring the various stalls, sampling the local delicacies, and chatting with the friendly vendors. The atmosphere is festive and welcoming, with something for everyone to enjoy. The live music and entertainment add to the fun, making it a great day out for the whole family.
The Sleepy Hollow Street Fair is a wonderful way to experience the local culture and community spirit. It’s a highlight of the town’s calendar and a must-visit for anyone in the area.
19. Rockefeller State Park Preserve
A visit to the Rockefeller State Park Preserve offers a peaceful escape into nature, with well-maintained trails and beautiful views of the Hudson River. The preserve is a haven for outdoor enthusiasts, with a wide variety of trails to explore, each offering its own unique scenery and challenges.
I enjoyed a leisurely hike through the preserve, taking in the stunning views and the tranquility of the surroundings. The trails are well-marked and suitable for all levels of fitness, making it an accessible and enjoyable experience for everyone.
The Rockefeller State Park Preserve is also a great spot for birdwatching, with a wide variety of bird species to be seen. It’s a perfect place to connect with nature and enjoy the beauty of the Hudson Valley.
Seasonal activities include horseback riding, carriage driving, geocaching (park permission required), hiking, fishing (New York State fishing license and Rockefeller Park permit required), picnics, and recreational running. Cross-country skiing, snowshoeing, and sledding slopes are all available in the winter. Family pets are permitted on a leash.
20. Unique Seasonal Performances
During the month of October, Sleepy Hollow becomes a host to some of the most unique shows in the tristate area. Aside from the various tours and events held throughout the year at notable Sleepy Hollow locations, there are handful of intriguing performances you won’t want to miss!
First, there is The Legend Cirque. Due to their popularity, the show returns for a second season. An amazing exhibition of acrobatic prowess will bring The Legend of Sleepy Hollow to life.
Brom Bones and Ichabod Crane fight it out for Katrina Van Tassel’s hand, while the Headless Horseman makes a surprising comeback. The performance will have you on the edge of your seat, so don’t miss it!
Then, at the Tarrytown Music Hall, the terrifying and humorous Dracula and the Theater of Doom is back for another year!
Dracula and the Theater of Doom transports viewers along with the protagonists through the legendary Tarrytown Music Hall’s frightening spaces. Join the audience as it follows Dracula, Van Helsing, and the rest of the cast from the vast stage of the theater through the darkest catacombs beneath it to the dazzling heights of its balcony for a heart-wrenching ending!
Two amazing shows you won’t want to miss!
21. Sleepy Hollow Lighthouse
Kingsland Point Park, 299 Palmer Avenue, Sleepy Hollow, NY
Visit the historic Sleepy Hollow Lighthouse, a redbrick tower from 1883, that served as a beacon for shipping on the Hudson River.
This lighthouse, which has been guiding ships on the Hudson River since the 19th century, is now open to the public, offering stunning views of the river and the surrounding landscape.
Besides enjoying the view, visitors can also explore the lighthouse’s museum, filled with exhibits about the lighthouse’s history and the maritime history of the Hudson River.
22. Camping at Sleepy Hollow
Why not enhance your trip with one of the most incredible ways to experience it all by spending a night or two camping?
Picture yourself surrounded by lush greenery, with the sound of babbling streams in the background. The parks are brimming with opportunities, from gentle hiking trails to exciting bike paths. There are world-class fishing spots and even opportunities for kayaking or canoeing on the Hudson River.
Sleepy Hollow is a place where you can reconnect with nature, with lectures and presentations available at the campsite to educate visitors on the area’s ecology.
🏕️Croton Point Park – Croton Point Avenue, Croton-on-Hudson, NY
🏕️Newburgh KOA Holiday – 119 Freetown Highway, Plattekill, NY
🏕️ Mountain Lakes Park – 201 Hawley Road, North Salem, NY
23. Grab a Drink at Some Great Pubs and Bars
We got the chance to spend a couple of evenings at the local pubs and bars in Sleepy Hollow, enjoying the lively atmosphere and the friendly locals. The historic charm of these establishments adds to the experience, making it a great place to unwind and socialize.
🍺Beekman Ale House – 92 Beekman Avenue, Sleepy Hollow, NY
🍺Bridge View Tavern – 226 Beekman Avenue, Sleepy Hollow
🍺Captain Lawrence Brewing Company – 444 Saw Mill River Road, Elmsford, NY
🍺Horsefeathers – 94 North Broadway, Tarrytown, NY
🍺 JP Doyle Restaurant and Public House – 48 Beekman Avenue, Sleepy Hollow
🍺Set Back Inn – 33 Main Street, Tarrytown
24. Grab Afternoon Tea at the Eatarry
Why settle for a typical lunch when you can indulge in a delicious afternoon tea?
The Eatarry boasts a charming atmosphere that will make you feel transported to another era. Whether you’re a local looking for a special outing, or a tourist seeking out unique things to do in Sleepy Hollow, this charming eatery is well-worth a visit.
Sip on sweet and savory teas, whilst nibbling on freshly made scones, dainty sandwiches and other tasty treats – all with a touch of whimsy and charm.
25. Where To Eat in Sleepy Hollow
Sleepy Hollow has plenty of places to grab a quick bite or full course dinner. Some of my favorite spots include Grass Roots Kitchen for a hearty yet healthy meal and smoothies and The Bakehouse for its relaxed atmosphere and delicious coffee and pastries. We even got a box of cupcakes to go!
Breakfast
☕ The Bakehouse – 2 Depot Plaza, Tarrytown, NY
☕Bella’s Restaurant – 5 S Broadway, Tarrytown, NY
☕Muddy Waters Coffee and Cafe – 52 Main Street
Tarrytown, NY
Lunch and Dinner
🍽️ The Hudson Anchor – 222 Beekman Avenue, Sleepy Hollow, NY
🍽️ Hudson Farmer and the Fish – 11 River Street, Sleepy Hollow, NY
🍽️ Grass Roots Kitchen – 124 Wildey Street, Tarrytown, New York
🍽️ Goosefeather – 49 E Sunnyside Lane, Tarrytown, NY
Need A Place To Stay In Sleepy Hollow?
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Sleepy Hollow, NY FAQ
Is Sleepy Hollow Worth Visiting?
Absolutely! Besides having connections to one of the most famous American legends, this charming town is great to add onto any New York road trip itinerary or for a nice weekend get away.
When Should I Visit Sleepy Hollow?
If your looking for something spooky to do this October, Sleepy Hollow is a great place to check out!
Any time of the year makes this city worth while to check out, but it can get cold during the winter months.
Is Sleepy Hollow A Walkable Town?
The downtown and historic district are walkable, but many places we highlighted are a bit of ways from each other. We recommend bringing or renting a car.
Is Sleepy Hollow And Tarrytown The Same Place?
Sleepy Hollow and Tarrytown are two separate small cities. They are right next to each other making it easy to travel to one another.
Why Is Sleepy Hollow Famous?
Sleepy Hollow served as inspiration for the famed ghost story by Washington Irving titled “The Legend of Sleepy Hollow”.
Conclusion: 25 Amazing Things To Do In Sleepy Hollow, NY for 2024
My visit to Sleepy Hollow was an adventure I won’t soon forget. From haunted attractions and historical landmarks to natural beauty and artistic treasures, this village offers a unique blend of experiences that cater to a wide range of interests.
If you’re planning a trip, make sure to include these unique and unusual things to do in Sleepy Hollow, NY. You won’t be disappointed.
