Destinations How to Plan the Perfect Trip to Sleepy Hollow, New York This small town is a fabled Halloween destination packed with history — and it's less than an hour from NYC by train. By Lauren Dana Ellman Lauren Dana Ellman Lauren Dana Ellman is a New York-based freelance writer and editor who specializes in travel, lifestyle, food, and shopping content. Travel + Leisure Editorial Guidelines Published on October 1, 2023 In This Article View All In This Article Where to Stay in Sleepy Hollow Things to Do in Sleepy Hollow Where to Eat and Drink in Sleepy Hollow Halloween in Sleepy Hollow Best Time to Visit How to Get There Trending Videos Close this video player Photo: OlegAlbinsky/Getty Images Less than 30 miles from Midtown Manhattan lies the quaint village of Sleepy Hollow in Westchester County, New York. Each fall, the otherwise unassuming destination, which has a population of just under 11,000, lures in throngs of thrill-seeking travelers. What’s more, explains Natasha Caputo, director of Westchester County Tourism & Film, the dynamic village is renowned for its rich history and deep-rooted connection to Washington Irving's 1820 tale, “The Legend of Sleepy Hollow.” Although a visit to Sleepy Hollow is a must during the spooky season, it’s sure to be crowded, which is why travelers will want to plan ahead as much as possible. With this in mind, we’ve compiled the ultimate guide to Sleepy Hollow during the Halloween season, along with tips, recommendations, and expert insights to help plan your visit any time of year (because it’s not all about Halloween). Where to Stay in Sleepy Hollow Sleepy Hollow Hotel The Sleepy Hollow Hotel is one of the village’s very few hotels. The property spans 11 acres of grassy, tree-lined grounds. When guests aren’t out and about exploring, they can be found swimming in the lap pool, relaxing in the sauna, or digging into breakfast staples like omelets and fresh-baked pastries at the charming Bistro Z Restaurant. Tarrytown House Estate on the Hudson A few minutes down the road in nearby Tarrytown, travelers can choose from historic hotels with castle-like exteriors. Tarrytown House Estate on The Hudson is ideal for families with its year-round indoor pool (there is also an outdoor pool for adults that’s open seasonally) and on-site sports like tennis, racquetball, bocce ball, and volleyball. The sprawling 26-acre grounds and the stylish Goosefeather restaurant (which serves traditional Cantonese-style fare with a modern twist) are added bonuses. Lucky visitors may even spot the resident ghost lingering on the second floor of the King House. The Castle Hotel & Spa The Castle Hotel & Spa is the perfect place for a romantic escape. Surrounded by 10 acres of tranquil woodland, the renovated castle features 31 rooms and suites, some of which boast en-suite fireplaces, marble baths, and four-poster beds. Additional hotel highlights include an upscale American eatery, a spa, a cozy library, and manicured gardens. John Greim/LightRocket via Getty Images Things to Do in Sleepy Hollow Kykuit, the Rockefeller Estate This former residence of the Rockefeller family — including a 40-room mansion and surrounding gardens — is now a historic landmark that's open seasonally between May and November. What’s more, says Caputo, “Its gardens and art collections are truly captivating, making it a must-visit, regardless of the season.” Visitors can choose from a handful of tour options, which can be found online. Philipsburg Manor Travelers can visit Philipsburg Manor, a former mill and trading complex owned and operated by the prominent Philipse family, to learn more about the enslaved individuals who lived and worked here in the 18th century. Keep in mind that the site is only open on select dates between May and December. Old Dutch Church The Old Dutch Church dates back to 1685 and is most famous for appearing in “The Legend of Sleepy Hollow.” Its 2.5-acre burying ground serves as the supposed home of the Headless Horseman in the spooky tale. Sleepy Hollow Cemetery The historic Sleepy Hollow Cemetery serves as the final resting place for over 45,000 individuals, including Irving. The 90-acre, 1849-era cemetery is open daily from Monday to Friday and offers several types of walking tours. Just outside the cemetery, you’ll find the iconic Headless Horseman Bridge and the Headless Horseman Statue. Where to Eat and Drink in Sleepy Hollow Hudson Farmer & The Fish Situated on the Sleepy Hollow Riverwalk, Hudson Farmer & The Fish features “seasonal specialties from their farm, along with a full raw bar, pizza, and modern takes on favorite seafood classics,” says Sarah Marshall, senior marketing manager of Westchester County Tourism & Film. While travelers can’t go wrong with anything on the menu, consider trying one of the autumnal-inspired dishes like pumpkin bisque and fall harvest hash. Meanwhile, the beautiful Hudson River views are an incredible added bonus. J.P. Doyle's “J.P. Doyle's stands out as a charming Irish pub and restaurant, celebrated for its warm and welcoming atmosphere,” says Marshall. Both locals and visitors alike can be found inside this friendly neighborhood haunt. It’s also here where travelers will find one of the best burgers in town (aptly named the Horseman Burger). Bridge View Tavern According to Marshall, beer enthusiasts will especially love Bridge View Tavern for its impressive craft beer selection. Visitors can pair their brews with delicious pub fare like pulled pork sandwiches, disco fries, and chicken wings, which are smoked in-house. Hudson Anchor Restaurant From pasta to steak to seafood, Hudson Anchor Restaurant has it all — not to mention an incredible happy hour special (20 percent off all cocktails, beer, wine, and food at the bar Mondays-Fridays from 3:00 p.m. to 6:00 p.m.). If the weather’s nice, nab a seat on the outdoor rooftop deck. It’s also worth noting that the restaurant’s beloved weekend brunch is unavailable in October. Santorini Greek Restaurant Craving Greek cuisine? Look no further than Santorini Greek Restaurant. Menu highlights include any of the dips (served with fresh pita) and gyros. John Greim/LightRocket via Getty Images Halloween in Sleepy Hollow Given the village’s history, it should come as no surprise that Sleepy Hollow truly comes to life during the spooky season. Expect an array of Halloween-centric events, drawing in hundreds, if not thousands, of tourists. Keep scrolling for a few of the highlights. The Legend Cirque This immersive performance, an adaptation of “The Legend of Sleepy Hollow,” is set in the early 19th century and is narrated by Irving himself (in hologram form, that is). It features exhilarating live-action circus performances that’ll have guests at the edge of their seats. The Legend Cirque runs through Oct. 29 and is best suited for those ages eight and up. The Horsemen: Terror Lies in Chaos Thrill-seekers need not miss this spectacular haunted house experience, which runs from Oct. 6 through Nov. 5. Located at the Kathryn Davis RiverWalk Center in Kingsland Point Park, this interactive haunted house focuses on finding and destroying a headless horseman (aptly named Chaos). Just keep in mind that this attraction is not for the faint of heart: No one under 16 is allowed without a chaperone; however, per the website, it’s highly recommended that those under 12 sit this one out. Sleepy Hollow Cemetery To ring in the spooky season, Sleepy Hollow Cemetery hosts an array of special events, including a murder mystery bash and evenings with Washington Irving and Edgar Allan Poe (who are portrayed by local storytellers). For something less scary — albeit just as fun — visitors can partake in an art class to create their own haunted cemetery canvas painting. Additionally, as previously mentioned, the cemetery offers a handful of tours to choose from, including several nighttime options, which, per Caputo, are “an absolute must” for “those with an appetite for the mysterious.” What’s more, she says, “These tours offer a unique opportunity to delve into the lives of its famous residents and learn about the legend of Sleepy Hollow, all beneath the eerie, moonlit skies.” SUP Witches Festival Taking place on Oct. 15, the fourth annual SUP Witches Festival is a sight to be seen. You can watch in awe as a group of “witches” gather to paddle at Horan's Landing – or join in on the fun. (Note that advance registration, as well as costumes, are required.) Even those who don't get in the water can enjoy the event with live music, food, and brews. Haunted Hayride and Block Party Plan your visit for Oct. 20 or 21 to hop aboard the Haunted Hayride, which carries passengers via hay wagon through downtown before detouring past the Old Dutch Church. Eventually, you’ll get through a set of iron gates — before slipping into the darkness with the sound of hoofbeats and shrieks in the distance. Post-hayride, visitors can enjoy the free block party on Beekman Avenue, featuring live music, entertainment, family-friendly activities, and much more. Sleepy Hollow “Run for Your Life” Halloween 10K On Oct. 28, Sleepy Hollow will host its annual “Run for Your Life” Halloween 10K. The family-friendly event draws kid and adult runners, and for a fun Halloween twist, participants are encouraged to dress up. Irving’s Legend at Washington Irving's Sunnyside On select dates, visitors can head to nearby Tarrytown to tour Irving’s home, which is decorated in festive fall decor. Caputo tells T+L, “Here, the legend of the Headless Horseman comes to life, enveloping visitors in a chilling narrative that's not for the faint of heart.” While the event is only open through Halloween, the estate itself doesn’t close until Dec. 17. Lyndhurst Lyndhurst, a historic mansion in neighboring Tarrytown, is also well worth a visit, says Caputo. “The 'Classic Fall Mansion Tour at Lyndhurst' allows visitors to journey through a historic mansion adorned in the splendor of autumn.” Alternatively, plan your visit during the evening hours to check out Lyndhurst After Dark, when the mansion is draped in candlelight. Best Time to Visit The best time to visit Sleepy Hollow ultimately depends on your interests. For example, those with an affinity for all things spooky will want to travel here during the fall season, “especially in October when the Halloween events and foliage are at their peak,” says Caputo. However, Sleepy Hollow also makes a great weekend getaway any time of year, especially considering its proximity to New York City. OlegAlbinsky/Getty Images How to Get There Visitors arriving by car will find the village conveniently located near major thoroughfares such as I-287 and the Saw Mill River Parkway. “Alternatively,” says Caputo, “for a stress-free journey, you can opt for public transportation by taking a Metro-North train to either Philipse Manor Station in Sleepy Hollow or the Tarrytown station.” Both stations are a short walk or drive from Sleepy Hollow’s most charming attractions. It’s also worth noting that Westchester County Airport is just 20 miles away, while other NYC airports like LaGuardia (LGA), John F. Kennedy (JFK), and Newark (EWR) are all within a 45-mile radius.