Less than 30 miles from Midtown Manhattan lies the quaint village of Sleepy Hollow in Westchester County, New York. Every fall, this low-key tourist destination with a population of less than 11,000 attracts a large number of thrill-seeking tourists.
Additionally, Westchester County Director of Tourism & Film, Natasha Caputo, explained that this vibrant village is known for its rich history and deep-rooted ties to Washington Irving’s 1820 story, The Legend of Guillotine Valley. Although going to Guillotine Valley during the horror season is a must, it is sure to be crowded there, which is why travelers plan as far in advance as possible. With that in mind, we’ve compiled the ultimate guide to Guillotine Valley during Halloween, along with tips, advice, and expert insights to help you plan your visit at any time of the year (because it’s not just Halloween).
Where to Stay in Sleepy Hollow
Sleepy Hollow Hotel
The Guillotine Valley Hotel is one of the few hotels in the village. The property is set on 11 acres of green grass and shaded by trees. When guests aren’t out exploring, they can swim in the plunge pool, relax in the sauna, or enjoy breakfast staples like omelets and freshly baked pastries at the charming Bistro Z restaurant.
Tarrytown House Estate on the Hudson
Just a few minutes’ walk down the road to nearby Tarrytown, visitors can choose from historic hotels with castle-like looks. Ideal for families, Tarrytown House Estate on The Hudson has a year-round indoor pool (and a seasonal outdoor pool for adults) and on-site sports facilities such as tennis, squash, bocce and volleyball. The sprawling 26-acre grounds and the stylish Goosefeather restaurant, which serves traditional Cantonese cuisine with a modern twist, are additional highlights. Lucky visitors may even spot the resident ghost hovering the second floor of the King’s Building.
Castle Hotel & Spa
The Castle Hotel & Spa is the perfect place for a romantic getaway. Surrounded by 10 acres of tranquil woodland, this renovated castle features 31 rooms and suites, some with ensuite fireplaces, marble bathrooms and four-poster beds. Other highlights of the hotel include an upscale American restaurant, a spa, a cozy library, and manicured gardens.
Things to Do in Sleepy Hollow
Kykuit, the Rockefeller Estate
The former home of the Rockefeller family — which includes a 40-room mansion and surrounding gardens — is now a historic landmark that is open seasonally from May to November. What’s more, its gardens and art collection are truly fascinating, making it a must-visit no matter the season. Tourists can choose from a number of tour options found online.
Philipsburg Manor
Visitors can visit Philipsburg Manor, a former mill and trading complex owned and operated by the famous Philipse family, and learn more about the slaves who lived and worked here in the 18th century. Keep in mind that the site is only open on specific dates between May and December.
Old Dutch Church
The Old Dutch Church dates back to 1685 and is best known for its appearance in The Legend of Guillotine Valley. Its 2.5-acre cemetery is believed to be the home of the Headless Horseman in horror stories.
Sleepy Hollow Cemetery
The historic Sleepy Hollow Cemetery is the final resting place of more than 45,000 people, including Owen. Built in 1849, the cemetery is spread over 90 acres and is open every Monday through Friday and offers several types of walking tours. Just outside the cemetery, you’ll find the iconic Headless Knight’s Bridge and Headless Horseman statue.
Where to Eat and Drink in Sleepy Hollow
Hudson Farmer & The Fish
Located on the Sleepy Hollow Riverwalk, Hudson Farmer & The Fish features seasonal specialties from the farm, a full raw food bar, pizza and a modern twist on the most popular seafood classics. While you can’t go wrong with any of the items on the menu, consider trying one of the fall-inspired dishes, such as pumpkin bisque and autumn harvest hash. At the same time, the beautiful view of the Hudson River is an incredible added bonus.
JP Doyle’s
JP Doyle’s is a charming Irish pub and restaurant known for its warm and welcoming atmosphere. Locals and tourists alike can find a spot in this friendly neighborhood. Here, visitors can also find one of the best burgers in town (aptly named “Knight’s Burger”).
Bridge View Tavern
Beer lovers will especially love the Bridge View Tavern as it offers an impressive selection of craft beers. Visitors can pair their beers with delicious pub fare such as pulled pork sandwiches, disco fries, and in-house smoked chicken wings.
Hudson Anchor Restaurant
From pasta to steaks to seafood, Hudson Anchor has it all, not to mention incredible happy hour specials (20% off all cocktails, beer, wine, and food at the bar every Monday through Friday from 3:00 p.m. to 6:00 p.m. afternoon). If the weather is nice, you can find a seat on the outdoor rooftop deck. It’s also worth noting that the restaurant’s beloved weekend brunch isn’t available in October.
Santorini Greek Restaurant
In the mood for Greek food? Look no further than Santorini Greek Restaurant. Menu highlights include any dip (served with fresh pita) and gyroscopes.
Best Time to Visit
The best time to visit the Valley of the Guillotine ultimately depends on your interests. For example, those who are interested in all things scary will want to travel here in the fall, especially in October, when Halloween events and leaves are at their highest. However, Guillotine Valley is a great weekend getaway at any time of the year, especially considering its proximity to New York City.
How to Get There
Visitors arriving by car will find the village conveniently located close to major thoroughfares such as Interstate 287 and Sawmill River Boulevard. Alternatively, for a stress-free ride, you can opt for public transportation and take the Northern Line train to Phillips Manor Station or Tarrytown Station in Deadhead Valley. Both stations are just a short walk or drive from Sleepy Hollow’s most fascinating attractions.
It’s also worth noting that Westchester County Airport is just 20 miles away, while other New York airports like LaGuardia (LGA), John F. Kennedy (JFK), and Newark (EWR) are all within a 45-mile radius.