On a recent late-summer Saturday afternoon, Sleepy Hollow was celebrating its birthday.
The village, nestled on the bank of the Hudson, was marking its 150th anniversary. Local officials modestly dubbed the event a “block party,” but the gathering drew throngs of visitors and featured several live music performances, fireworks, and food trucks.
Village residents were just one portion of the partygoers. “It’s interesting,” said Martin Rutyna, the village’s mayor, a few hours before the event. “I hear people are coming from other states, as far as down South.”
However well-attended the so-called block party was, an even bigger moment — and influx of visitors — was on the horizon. “The block party has always been a last hurrah for us locals before the busy Halloween season,” Rutyna explains. Each year, tens of thousands of people amble through the historic graveyard, gawk at autumn leaves, and soak in the atmosphere Washington Irving captured in his 1820 short story The Legend of Sleepy Hollow. “We see people not just from across the United States, but also Europe and Asia,” Rutyna says.
Sleepy Hollow may be Westchester’s most popular October destination, but many other corners of the county draw far-flung tourists — and not just during the fall months. For residents who have lived in Westchester for years, it’s easy to develop a blind spot. Many locals describe their home county as a sleepy suburb or bedroom community. But that belies the truth: Tourism is a major and growing engine for Westchester’s economy. “Visitor spending is over $2 billion a year,” says Westchester County Executive George Latimer.
“Over the past few years, Westchester County has undertaken several key initiatives to boost tourism, leveraging strategic funding, and innovative marketing campaigns,” explains Natasha Caputo, director of Westchester County Tourism and Film, an organization housed in the office of the county executive. For proof of the impact, just look to Peekskill, where the recently opened Abbey Inn and Spa towers over the Hudson River and has earned Michelin accolades. Or look to county headquarters, where the county government earlier this year released the first-ever (and 60-page) Westchester Official Travel & Meeting Guide.
Westchester is also an increasingly coveted destination for movie and television productions, with casts and crews flocking to its charming downtowns, rolling hills, and historic enclaves. In 2023, filming in Westchester generated more than half a billion dollars in economic impact, according to county analysis, and buoyed more than 2,000 jobs. If you didn’t manage to catch sight of the sets, you likely saw one of the finished products: Television series “Severance,” “The Gilded Age,” and “Succession” all have filmed in Westchester in the past few years.
“This influx of filming has had a ripple effect, driving tourism as visitors are drawn to recognizable filming locations, while also boosting local pride and creating a sense of cultural excitement,” Latimer says.
Drawing From Afar
Fifteen miles southeast of Sleepy Hollow, on the county’s other waterfront, sits one of Westchester’s longest-running attractions: Rye Playland. It’s one of the country’s oldest attractions of its kind, too, and has the distinction of being the first-ever planned amusement park in the United States.
The park’s vintage wooden roller coaster and Ferris wheel have been drawing out-of-county visitors since the early 20th century when the park was built. “Playland was designed using art-deco architecture and is designated a National Historical Landmark,” explains Evonne Keeler, CEO of Playland. The park has changed over the years — new rides, different ownership — but its lure hasn’t faded.
“We welcome visitors from the greater New York City metro area including the five boroughs, Long Island, the Lower Hudson Valley, and Fairfield County in Connecticut,” Keeler says. Then there are the folks who travel from farther afield: “Our accessibility has also allowed us to welcome tourists and visitors from all over the globe,” she adds.
Playland’s mix of recreation, dining, and entertainment without requiring a plane ticket to Florida or California is a magnet for those in the surrounding environs. “Our iconic amusement park features over 50 rides and attractions, including the historic Derby Racer, The Whip, and The Dragon Coaster, which turned 95 years old this year,” Keeler says. For those not seeking thrills, there are also beaches, fishing and paddleboarding on the park’s placid lake, and almost two miles of publicly accessible boardwalk.
Recently, the park has doubled down on attracting out-of-county visitors. “During our peak summer season this year, we relaunched a ferry service directly from New York City, allowing us to welcome our tourists via boat, train, bus, and beyond,” Keeler says.
Playland in summer and Sleepy Hollow in fall are a major boon to surrounding merchants. Each October in Sleepy Hollow, for example, “The locals say goodbye to our restaurants,” Rutyna jokes. “We welcome the extra traffic. It sustains [us] the rest of the year. And it’s a benefit for everyone: not just Sleepy Hollow, but Tarrytown, Irvington, Ossining — all the way up to Croton.”
All this economic activity adds up: “This revenue supports small businesses, encourages investment in real estate and cultural institutions, and attracts long-term business opportunities,” Latimer explains. “It sustains thousands of jobs, drives tax revenue for public services, and funds infrastructure improvements.”
But not all who vacation in Westchester are outsiders. The county’s diversity — a mix of bustling cities and remote hamlets, lively nightlife, and untamed wilderness — means even locals can plot a getaway. At the Royal Regency Hotel in Yonkers, owner Maria Pampafikos says guests often aren’t far from home. “We draw visitors from Bronxville, New Rochelle, and Mamaroneck,” she says. Indeed, although the hotel also attracts guests from across the Tristate area, much of its advertising is focused on folks already within the county’s borders.
“Common reasons for visits include personal getaways,” Pampafikos says. “We’re just minutes from attractions like the MGM Empire City Casino and the Cross County Shopping Center.”
Hollywood Alternative
For those who’d rather escape into a film rather than a vacation, Westchester is still a viable option — more and more, the county is showing up on screens big and small. “Westchester County has become a premier destination for film production because we offer the complete package: diverse locations, film-friendly communities, and a skilled and supportive workforce,” says Caputo of Westchester County Tourism and Film. “[These are] exactly what producers need to bring their creative visions to life.”
“Film production has a significant economic impact,” Caputo says, noting it supported nearly 7,000 local jobs between 2022 and 2023.
—Director, Tourism and Film, Natasha Caputo
“Westchester makes filming easy, offering a wide range of locations — from historic estates and rural scenes to vibrant urban centers with high-tech spaces,” Caputo adds.
Creatives agree. In a county press release from earlier this year, “The Gilded Age” director Michael Engler gushed about the county: “[Westchester has] these magnificent homes and estates which bear the unmistakable imprint of the Gilded Age,” he said. “We also shoot up there because of the space — land, big parking lots, parks, and pathways. People were extremely friendly and gracious. We all love shooting in Westchester.”
Westchester also makes filming cheaper — relative to renting space and purchasing permits in New York City. “Many of our locations fall within the NYC film zone, offering productions based in the city cost-effective benefits when filming in Westchester,” Caputo says.
Some studios do more than make a day trip to Westchester. Since Great Point Studios put down roots in Yonkers, its lots and stages have contributed to a major revitalization in the heart of Westchester’s largest city. “Film production has a significant economic impact,” Caputo says, noting it supported nearly 7,000 local jobs between 2022 and 2023.
Then there’s the intangible aspect: “It brings Westchester communities together, inspires young filmmakers, and adds a touch of glamour to our lives,” she says. “It’s exciting to have film crews in our municipalities and a point of hometown pride to see our neighborhoods on the big or small screen.”
Westchester’s momentum for attracting tourists and filmmakers doesn’t appear to be slowing down. At the time of this reporting, the county — not just Sleepy Hollow — is preparing for a wave of autumn visitors. “Westchester is set to attract an influx of visitors with apple and pumpkin picking, new local brew and cider servings, themed historic mansion tours, exciting trails for peeping fall foliage, and much more,” Caputo says. This comes just months after the county debuted its Westchester Craft Beverage Trail, a mobile passport program that links local breweries and cideries for craft-beer connoisseurs.
There’s more on the horizon. Upcoming in 2026 is the U.S. Semiquincentennial — that is, our nation’s 250th birthday. The county anticipates history buffs will descend on its Revolutionary War battlegrounds and other historic locations. All the while, Caputo says, county officials will strive to “solidify Westchester as a premier travel destination for unique and memorable experiences.”
Related: 5 Standout Outdoor Destinations in Westchester County
