This Legendary Halloween Destination Is Just 30 Miles From NYC—With Spooky Events and Vibrant Foliage Every Fall

Less than 30 miles from Midtown Manhattan is the quaint village of Sleepy Hollow in New York’s Westchester County. Each fall, the otherwise unassuming destination, which has a population of about 11,000, lures in throngs of travelers looking for thrills and hauntings.

What’s more, 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

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 Hudson Bistro 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, like the Tarrytown House Estate. This property is ideal for families because of its year-round indoor pool (there’s also an adults-only outdoor pool 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.

Things to Do

Kykuit, the Rockefeller Estate

The Rockefeller family’s former estate—including a 40-room mansion and surrounding gardens—is now a historic landmark that’s open seasonally between May and November. Natasha Caputo, director of Westchester County Tourism & Filmtold Travel + Leisure that “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.

Philipsburg Manor

Travelers can visit Philipsburg Manora 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 cemetery serves as the supposed home of the Headless Horseman in the spooky tale, and if you walk just a few minutes down the road, you’ll find the Headless Horseman Bridge and a statue depicting the character.

Sleepy Hollow Cemetery

The historic Sleepy Hollow Cemetery is the final resting place for about 47,000 individuals, including Irving. The 90-acre, 1849 cemetery is open daily from Monday to Friday and offers several types of walking tours.

Where to Eat and Drink

Hudson Farmer & The Fish

Situated on the Sleepy Hollow Riverwalk, Hudson Farmer & The Fish has a full raw bar, pizza offerings, and modern spins on seafood favorites. While you can’t go wrong with anything on the menu, consider trying one of the seasonal fall dishes. In the past, autumnal features have included 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 Sarah Marshall, senior marketing manager of Westchester County Tourism & Film. Locals and visitors alike can be found inside this friendly neighborhood haunt. It’s also here where you can order one of the best burgers in town (aptly named “the Horseman”).

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.

Santorini Greek Restaurant

Craving some fresh Mediterranean flavors in this town of pubs and seafood haunts? Look no further than Santorini Greek Restaurant. Menu highlights include any of the dips (served with fresh pita) and gyros.

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 thousands of tourists. Keep scrolling for a few of the highlights.

Sleepy Hollow Cemetery

To ring in the spooky season, Sleepy Hollow Cemetery hosts an array of special eventsincluding 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—you can sign up to paint your own Headless Horseman on a wooden pumpkin.

Additionally, the night tours of the cemetery are “an absolute must” for “those with an appetite for the mysterious,” per Caputo. “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,” she says.

SUP Witches Festival

Taking place on Oct. 12, the fifth annual SUP Witches Festival is a sight to be seen. You can watch in awe as a group of “witches” gather to paddleboard from Kingsland Point Park—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. 17 or 18 to hop aboard the Haunted Hayridewhich carries passengers via hay wagon through downtown before detouring past the Old Dutch Church. Eventually, you’ll go through iron gates into the darkness, with only 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 more.

Sleepy Hollow “Run for Your Life” Halloween 10K

On Oct. 25, 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 homewhich 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

Lyndhursta historic mansion in 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 Darkwhen 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.

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 charming attractions.

It’s also worth noting that Westchester County Airport is just 16 miles away, while other NYC airports like LaGuardia (LGA), John F. Kennedy (JFK), and Newark (EWR) are all within a 50-mile radius.