How to Plan an Unforgettable Trip to Sleepy Hollow, New York

Nestled less than 30 miles from Midtown Manhattan, the charming village of Sleepy Hollow in Westchester County, New York, attracts a flood of adventurous visitors each fall. With a population just shy of 11,000, this otherwise quiet destination transforms into a bustling hub of excitement during the spooky season.

Furthermore, as Natasha Caputo, director of Westchester County Tourism & Film, explains, this vibrant village is celebrated for its rich history and strong ties to Washington Irving's 1820 story, “The Legend of Sleepy Hollow.” While a visit during Halloween is highly recommended, it can get quite crowded, making it essential for travelers to plan ahead. To assist, we’ve created the ultimate guide to experiencing Sleepy Hollow during the Halloween season, complete with tips, recommendations, and expert insights for visits at any time of year (because it’s not just about Halloween).

Where to Stay in Sleepy Hollow

Sleepy Hollow Hotel

The Sleepy Hollow Hotel is one of the few accommodations in the village, set across 11 acres of lush, tree-lined grounds. When not exploring, guests can enjoy the lap pool, unwind in the sauna, or savor breakfast favorites like omelets and freshly baked pastries at the delightful Bistro Z Restaurant. 

Tarrytown House Estate on the Hudson

Just a short drive away in Tarrytown, visitors can find historic hotels with castle-like architecture. Tarrytown House Estate on The Hudson is perfect for families, featuring a year-round indoor pool and a seasonal outdoor pool for adults. On-site activities include tennis, racquetball, bocce ball, and volleyball. The expansive 26-acre grounds and the elegant Goosefeather restaurant, offering a modern take on traditional Cantonese cuisine, are additional highlights. Some lucky guests might even catch a glimpse of the resident ghost rumored to haunt the second floor of the King House. 

The Castle Hotel & Spa 

The Castle Hotel & Spa is the ideal destination for a romantic getaway. Nestled within 10 acres of serene woodlands, this beautifully renovated castle features 31 rooms and suites, some equipped with en-suite fireplaces, marble bathrooms, and four-poster beds. Other notable amenities include a fine American restaurant, a spa, a cozy library, and meticulously landscaped gardens.

Things to Do in Sleepy Hollow

Kykuit, the Rockefeller Estate

Once the home of the Rockefeller family, this 40-room mansion and its beautiful gardens are now a historic landmark open for visits from May to November. According to Caputo, “Its gardens and art collections are truly enchanting, making it a must-see at any time of year.” Guests can choose from several tour options available online.

Philipsburg Manor

Visitors can explore Philipsburg Manor, a historic mill and trading post that was once owned by the influential Philipse family, to learn about the lives of the enslaved individuals who worked here in the 18th century. Note that the site is open only on select days from May to December.

Old Dutch Church

The Old Dutch Church was built in 1685 and is best known for its appearance in “The Legend of Sleepy Hollow.” Its 2.5-acre graveyard is said to be the lair of the Headless Horseman from the chilling story.

Sleepy Hollow Cemetery  

The historic Sleepy Hollow Cemetery is the final resting place of over 45,000 people, including Washington Irving. This 90-acre cemetery, established in 1849, is open daily from Monday to Friday and features a variety of walking tours. Just outside, you'll encounter the famed Headless Horseman Bridge and the Headless Horseman Statue.

Where to Eat and Drink in Sleepy Hollow

Hudson Farmer & The Fish

Nestled along the Sleepy Hollow Riverwalk, Hudson Farmer & The Fish offers a menu brimming with “seasonal specialties from their farm, complemented by a full raw bar, pizzas, and contemporary twists on beloved seafood classics,” notes Sarah Marshall, senior marketing manager of Westchester County Tourism & Film. While any choice on the menu is sure to delight, don't miss out on autumn-inspired dishes like pumpkin bisque and fall harvest hash. Plus, the stunning views of the Hudson River are an incredible bonus. 

J.P. Doyle's

“J.P. Doyle's is a delightful Irish pub and restaurant, renowned for its cozy and inviting atmosphere,” says Marshall. This welcoming neighborhood spot attracts both locals and tourists alike. It’s also the place to find one of the best burgers around, aptly named the Horseman Burger. 

Bridge View Tavern

As Marshall highlights, Bridge View Tavern is a paradise for beer lovers, boasting an impressive selection of craft brews. Guests can enjoy their drinks alongside tasty pub fare such as pulled pork sandwiches, disco fries, and house-smoked chicken wings. 

Hudson Anchor Restaurant

Whether you're in the mood for pasta, steak, or seafood, Hudson Anchor Restaurant has you covered — plus an amazing happy hour (enjoy 20 percent off all cocktails, beer, wine, and food at the bar from Mondays to Fridays, 3:00 p.m. to 6:00 p.m.). If the weather permits, grab a spot on the outdoor rooftop deck. Just a heads-up, the popular weekend brunch isn't available in October.

Santorini Greek Restaurant

If you're craving Greek flavors, Santorini Greek Restaurant is the place to go. Must-try items include their delightful dips served with fresh pita and the classic gyros. 

Halloween in Sleepy Hollow 

With its rich history, it's no wonder that Sleepy Hollow truly comes alive during the Halloween season. Expect a variety of Halloween-themed events that attract hundreds, if not thousands, of visitors. Keep reading for some of the highlights.

The Legend Cirque

This immersive show offers a fresh take on “The Legend of Sleepy Hollow,” set in the early 19th century and narrated by Irving himself (in hologram form, of course). It includes thrilling live-action circus acts that will keep audiences on the edge of their seats. The Legend Cirque runs until October 29 and is recommended for ages eight and older.

The Horsemen: Terror Lies in Chaos

Adventurous souls won't want to miss this thrilling haunted house experience, running from October 6 to November 5. Located at the Kathryn Davis RiverWalk Center in Kingsland Point Park, this interactive attraction centers on the quest to find and defeat a headless horseman named Chaos. Please note that this experience is not for the faint-hearted: no one under 16 is permitted without an adult chaperone, and the website advises that children under 12 should probably skip it altogether.  

Sleepy Hollow Cemetery 

To celebrate the spooky season, Sleepy Hollow Cemetery hosts a variety of special events, including a murder mystery party and evenings featuring Washington Irving and Edgar Allan Poe, portrayed by local storytellers. For a less intense but equally enjoyable option, visitors can join an art class to create their own haunted cemetery canvas painting. 

Additionally, as mentioned earlier, the cemetery offers several tours, including various nighttime options that, according to Caputo, are “a must-do” for anyone with a taste for the eerie. She adds, “These tours provide a unique chance to explore the lives of its famous residents and uncover the legend of Sleepy Hollow under the haunting glow of the moon.” 

SUP Witches Festival

On October 15, prepare to be amazed at the fourth annual SUP Witches Festival. You can either watch as a group of “witches” paddle at Horan's Landing or join in the fun yourself. (Advance registration and costumes are mandatory.) Even those who prefer to stay dry can enjoy the festivities, complete with live music, food, and drinks. 

Haunted Hayride and Block Party

Mark your calendar for October 20 or 21 to take part in the Haunted Hayride, which transports guests on a hay wagon through downtown, making a thrilling detour past the Old Dutch Church. You'll pass through iron gates and into darkness, with hoofbeats and distant screams adding to the suspense. After the hayride, visitors can enjoy a free block party on Beekman Avenue, featuring live music, entertainment, family activities, and much more.

Sleepy Hollow “Run for Your Life” Halloween 10K 

On October 28, Sleepy Hollow will celebrate its annual “Run for Your Life” Halloween 10K. This family-friendly event attracts both kids and adult runners, and participants are encouraged to get creative with their costumes for a festive Halloween twist. 

Irving’s Legend at Washington Irving's Sunnyside 

On select dates, visitors can explore Irving’s home in nearby Tarrytown, which is adorned with charming fall decorations. Caputo shares with T+L, “Here, the legend of the Headless Horseman comes alive, immersing guests in a spine-chilling story that's not for the timid.” While this special event runs only through Halloween, the estate remains open until December 17. 

Lyndhurst

Lyndhurst, a historic mansion in nearby Tarrytown, is also a must-see, according to Caputo. “The 'Classic Fall Mansion Tour at Lyndhurst' offers guests a glimpse into a grand mansion adorned in autumn's beauty.” For a different experience, consider visiting during the evening to enjoy Lyndhurst After Dark, when the mansion is illuminated by candlelight. 

Optimal Time to Visit 

The ideal time to explore Sleepy Hollow largely depends on your preferences. Those who revel in the eerie ambiance should consider a fall visit, particularly in October when Halloween festivities and autumn foliage reach their zenith, according to Caputo. Nonetheless, Sleepy Hollow is also an excellent destination for a weekend retreat year-round, especially due to its close proximity to New York City. 

Directions to Get There

Travelers coming by car will find Sleepy Hollow conveniently positioned near key routes like I-287 and the Saw Mill River Parkway. “Alternatively,” Caputo suggests, “for a more relaxing trip, you can take public transportation by catching a Metro-North train to either Philipse Manor Station in Sleepy Hollow or the Tarrytown station.” Both stations are just a short walk or drive from the village's most delightful attractions. 

Additionally, it's important to mention that Westchester County Airport is located just 20 miles away, while other New York City airports such as LaGuardia (LGA), John F. Kennedy (JFK), and Newark (EWR) are all within a 45-mile distance.