The Open Road Travel

Situated twenty-five miles north of New York City, on the banks of the Hudson River, is the village of Sleepy Hollow. Best known for being the setting for the famous story “The Legend of Sleepy Hollow”, the village is one of America's favourite destinations for an Autumn trip.

However, despite Sleepy Hollow's reputation, very few people actually know what it has to offer when they arrive. That brings us to our list of the 8 best things to do in Sleepy Hollow.

We will include the very best attractions the town has to offer and cover all of the things that it is known for. So, if you are planning your own travel itinerary for when you visit Sleepy Hollow, this is the article for you.

Sleepy Hollow is a village in Westchester County in the state of New York and is home to a population of nearly 10,000 residents.

Sleepy Hollow’s history is rooted in Native American tribes and eventually Dutch colonists, who were the first Europeans to settle in the area.

Once known as North Tarrytown, Sleepy Hollow was renamed to capitalise on the aforementioned literary classic by resident writer, Washington Irving.

The village is steeped in history and is considered by some to be one of the most haunted places in the world. Ironically, Sleepy Hollow has also been named as one of the safest places in the US to live.

Sleepy Hollow is full of things to do any time of the year but, by far, the best time to visit Sleepy Hollow is during the Autumn months (fall).

Not only is the area especially beautiful in the autumn months with the changing of the leaves, but the town of Sleepy Hollow goes all out to celebrate Halloween in October too. It is considered by many to be the best place to spend Halloween in the United States.

However, there is also a range of outdoor adventures and activities on offer in the area too. So, if you aren't interested in Halloween, you might decide you want to visit from mid-June to late September, to get the most out of warm-weather ventures.

With plenty of stunning views, a historic downtown, and a wide variety of different activities available, there will be something for most people to enjoy in Sleepy Hollow.

Now without further delay, let’s move on to our list of the 8 best things to do in Sleepy Hollow and the surrounding area.

Founded in 1849, the historic Sleepy Hollow Cemetery is a must-see if you are planning on visiting the village. The 90-acre cemetery grounds contain over 45,000 graves, and there continue to be more burials taking place to this day.

Open daily, Sleepy Hollow Cemetery is the final resting place of some of the area’s most iconic residents, including the author of the legendary ‘Sleepy Hollow’ tale, Washington Irving.

Sleepy Hollow Cemetery can be explored either by yourself or with a tour group. Taking a guided tour will allow you to see many of the notable burial sites, including that of William Rockefeller, John Dustin Archbold, and Andrew Carnegie.

Despite how it may appear, it is not all doom and gloom at Sleepy Hollow Cemetery, and it can be a pleasant location to take a relaxing stroll, as the grounds themselves are full of greenery and are home to some striking monuments.

Sleepy Hollow Cemetery is great to visit at any time of the year but, of course, if you are visiting Sleepy Hollow over Halloween, you can’t miss this location off of your itinerary.

And if that’s the case, why not make your visit extra special and book a creepy, night-time, lantern-lit tour through the famous grounds?

Moving on from his final resting place, we now heat to where Washington Irving lived his life. The picturesque estate that Washington Irving called home is another great spot to see when you visit Sleepy Hollow.

The historic house is situated along the Hudson River and is technically not in Sleepy Hollow. It is instead located in Tarrytown, just 5 minutes away and less than a mile south of Sleepy Hollow.

Washington Irving was one of the most famous American authors of the 19th century and, along with “The Legend of Sleepy Hollow”, he is best known for other short stories such as “Rip van Winkle”.

Irving bought the two-room Dutch stone house in 1835 and extensively remodelled it.

Sunnyside, the enchanted residence of Irving, has been enticing visitors for generations and contains much of the original furniture and many of the author's personal possessions, including his books and writing desk.

Designated a National Historic Landmark in the 1960s, the old house is open for tours where visitors can learn all about the life of Washington Irving as well as local legends.

Kykuit, also known as the John D. Rockefeller Estate, is a 40-room historic mansion built between 1906 and 1913. Kykuit was once the hilltop, country home to four generations of the Rockefeller family, starting with the family patriarch and oil tycoon, John D. Rockefeller.

Now a historic site of the National Trust, Kykuit continues to be meticulously maintained and is a top cultural attraction in the area.

Situated on the highest point in Pocantico Hills, the colonial-style house has fantastic views over the Hudson River and even boasts a view of the New York City skyline to the south.

The residence and its stunning grounds are home to a collection of modern sculptures and fine furnishings, and the landscaped gardens and terraces are wonderful to stroll around while enjoying the sweeping views of the river and surrounding areas.

Tours of Kykuit run from May to mid-November and all start at the Visitor Centre at Philipsburg Manor, where you can catch a shuttle bus to the estate.

This brings us nicely on to our next location.

Once a thriving mill and trading complex, Philipsburg Manor, dating back to 1693, now operates as a museum. The manor is sometimes referred to as Philipse Manor, after Frederick Philipse, a Dutch immigrant that made the initial purchase of land.

If you’re into history, Philipsburg Manor is one of the top historic attractions and one of the absolute best things to do in Sleepy Hollow.

Take a guided tour and be transported back to 1750, where you will learn about the working mill, as well as the lives of the 23 slaves of African descent that were forced to work there.

Staff in period costume will give you an insight into early America and a glimpse into the lives of the Philipse family that owned the property.

Rockefeller State Park, situated just north of Sleepy Hollow in the eastern foothills of the Hudson River, is the ideal spot to unwind after busily exploring the village.

The Rockefeller State Park Preserve is the former county estates of the Rockefeller family and since 1983, over 1,700 acres of the land have been donated by them to the state of New York, in order to preserve the natural beauty for future generations.

Today, the park is open all year round and visitors can enjoy quiet walks along the 55 miles (88.5 kilometres) of carriage trails, with routes to accommodate all skill levels. Take in stunning views at scenic vistas, or even a ride on a horse along one of the many paths.

The forested hills, open meadows, and valleys are home to a wide variety of wildlife, including deer, chipmunks, raccoons, and bears, plus over 200 different bird species.

Finally, located right in the heart of Rockefeller State Park is the stunning body of water that is Swan Lake. The gravel trail around Swan Lake is a pleasant and popular spot for people hiking, running, or even fishing during certain seasons to unwind and enjoy its beauty.

Appropriately unveiled on Halloween in 2006, the Headless Horseman statue is one of the most visited spots in the village of Sleepy Hollow. The 18-foot-tall sculpture, created by a local artist, is situated between the Philipsburg Manor and the Old Dutch Church.

The statue is a depiction of the moment the headless horseman throws a pumpkin at Ichabod Crane, the protagonist in Washington Irving's book, and is definitely worth getting a picture of while you’re in the area.

Make sure to check out another monument to the Sleepy Hollow Legend at the entrance to Philipsburg Manor.

Presented to the village in 1974, this granite sculpture also depicts Ichabod Crane fleeing from the Headless Horseman.

The Tarrytown & Sleepy Hollow Farmers Market, or TaSH, takes place every Saturday from 8:30 am and is a great way to spend the morning.

While the mention of a farmers’ market may not enthral you like some of our other suggestions might have, TaSH is not an event to be overlooked if you're visiting the area. Held in the beautiful Patriots Park, on the border of Tarrytown and Sleepy Hollow, the market offers a wide range of products, including baked goods, beer, flowers, cheese, honey, and many fresh fruits and vegetables.

There is also occasionally live music and activities for children, making the market great for a family day out. Many other community events are regularly hosted in Patriots Park too, and there always tends to be some form of entertainment taking place.

Lastly, if you plan on visiting Sleepy Hollow at Halloween, your stay would not be complete without stopping at the biggest Halloween event the area has to offer.

The exceptionally popular, Great Jack O’Lantern Blaze is not actually held in Sleepy Hollow itself but takes place at Van Cortlandt Manor, which is around a 20-minute drive away in the idyllic village of Croton-on-Hudson.

Here, visitors can take a self-guided stroll through an 18th-century landscape on the grounds of the manor and witness the breath-taking display of more than 7,000 illuminated pumpkins, all skilfully designed and intricately carved on site.

The event, which began in 2005, has become hugely popular and the number of visitors continues to grow each year.

The Jack O Lantern Blaze is a fantastic event for those of all ages and everyone in attendance is sure to be in awe of the many displays, made entirely out of pumpkins and enhanced with the added effects of synchronized lights and music.

Also on site are tents that sell all kinds of wonderfully tasty, autumnal food and drink, such as candy apples, hot cocoa or cider, pumpkin spice treats, and even yummy pumpkin beer.

Tickets must be purchased in advance to experience this enchanting and unmissable event.

Located less than two miles away from Sleepy Hollow Cemetery, is the luxurious and truly magnificent Castle Hotel and Spa.

The hotel is technically in Tarrytown (like a lot of the previous locations mentioned) but with its high ceilings, stone walls, and original features, this is a hotel you will love.

Built in 1897 initially as a private residence, the Norman-style castle hotel is perched atop one of the highest points in the region and it boasts views of the Hudson River and its stunning landscaped grounds.

Thirty-one spacious, newly renovated, and refurbished rooms offer free Wi-Fi, and flat-screen TVs with access to popular streaming services, along with humidifiers and coffeemakers.

There are also luxurious tower suites available which contain 4-poster beds, marble bathrooms, and wood-burning fireplaces.

The Castle and Spa Hotel provides in-house spa services including relaxing massages and facials, along with an outdoor pool complex with a hot tub. There is also a sophisticated on-site restaurant.

Sleepy Hollow is a wonderful destination to discover at any time of the year but it is undeniably the perfect destination for a fall or Halloween trip. Many even like to see it as part of a road trip through New York State.

There really is something for everyone here, and with hiking trails, historic buildings, and beautiful surroundings, Sleepy Hollow has a little bit of everything.

I hope this list of the 8 best things to do in Sleepy Hollow has helped you decide on what you’d like to do and see during your trip so that you can now plan your ideal travel itinerary and get to booking an unforgettable vacation to this idyllic little town.