Nearly 100 costumed paddlers are expected to glide across the Hudson River Saturday, October 10, 2026, as Sleepy Hollow's SUP Witches Festival returns to Kingsland Point Park, transforming the waterfront into a floating coven of witches, ghosts and other Halloween characters. The event runs from noon to 5 p.m. at 299 Palmer Avenue, with the main group paddle launching at 2 p.m., and spectators can watch from shore for $8 in advance or $10 at the gate. If weather forces a postponement, the rain date is set for Sunday.
The paddle has come a long way from its humble beginnings. According to Secret NYC, the gathering started in 2020 as an informal group paddle organized by Tara Scheller, owner of Rivertowns SUP & Yoga, before the Village of Sleepy Hollow partnered with her to turn it into an official autumn tradition. What began with just 16 costumed participants in 2020 grew to more than 80 paddlers by 2023, and organizers now expect roughly 100 costumed paddlers on the water this year, according to Scenic Hudson.
Rivertowns SUP & Yoga, which Scheller established in 2018, now co-chairs the festival coven alongside certified paddle coaches and yoga instructors Leanne Duke and Chrissy Braun, per the organization. The festival itself draws thousands of spectators and dozens of floating witches each October, with the mass costumed paddle serving as the centerpiece of a waterfront celebration that also includes live music, food, local brews, vendors and family-friendly activities at Witches Hollow, the Secret NYC report notes.
What Paddlers Need To Know Before Jumping In
Anyone hoping to join the flotilla rather than just watch it had to register in advance by October 7, with registration covering festival access. Paddlers bringing their own board or kayak pay $35, while a limited number of SUP rentals are available for $50, though rental availability is restricted to Rivertowns SUP & Yoga customers, per the Secret NYC report.
Participation comes with real requirements. Paddlers must have prior river experience, be able to swim, and wear a mandatory costume along with a SUP leash and a personal flotation device, while organizers also advise wetsuits or quick-dry layers given the cold October water. Those requirements track with broader maritime law: under U.S. Coast Guard and New York State regulations, stand-up paddleboards operated outside designated swimming zones are classified as vessels, which legally requires each paddler on the Hudson River to carry or wear a Coast Guard-approved flotation device, according to Glide Paddleboards. Fall paddlers also face cold water immersion risks and active commercial vessel traffic in the nearby shipping channels.
Paddler check-in runs from 11 a.m. to noon, and the park gates close to unloading vehicles at 11:30 a.m. Spectators are advised to arrive by 1 to 1:30 p.m. to find a spot before the 2 p.m. launch, and children under 8 get in free with a paying adult. The festival has also become known for an unscripted bit of theater: the Headless Horseman has been known to make an appearance along the shore during the paddle, a nod to the folklore that put this village on the map.
A Village Built Around Its Own Ghost Story
That folklore runs deep here. Washington Irving published The Legend of Sleepy Hollow in 1820, setting his fictional tale in 1790 and drawing on local Revolutionary War folklore about a German mercenary soldier who lost his head in 1776 near Tarrytown, per Scenic Hudson. The village itself wasn't always named for the story — it was officially called North Tarrytown until 1996, when residents voted to change its name to Sleepy Hollow after the closure of its General Motors assembly plant, according to Business Insider.
That pivot has paid off. Sleepy Hollow and neighboring Tarrytown, each with year-round populations of roughly 11,000 residents, together draw between 100,000 and 150,000 visitors every October during peak Halloween tourism, per Lonely Planet contributor Beth Helvey. The scale of that draw was underscored this month when Travel and Tour World ranked Sleepy Hollow third among top Halloween travel destinations across the Americas and the Caribbean, trailing only Salem, Massachusetts, and Orlando, Florida.
The region's Halloween economy extends well beyond the village limits. Less than nine miles north in Croton-on-Hudson, Historic Hudson Valley's Great Jack O'Lantern Blaze draws up to 125,000 visitors over 52 autumn nights with 7,000 hand-carved illuminated pumpkins on display, according to River Journal Online.
Getting There Without Getting Stuck
Festival organizers are blunt about the logistics headache that comes with hosting thousands of visitors in a small waterfront village. Driving to Kingsland Point Park can involve severe weekend traffic delays along Route 9 and very limited parking, per the Secret NYC report, making the Metro-North Hudson Line — which runs directly from Grand Central Terminal to Sleepy Hollow — the more reliable option for many visitors.
Riders on express trains can travel to either Tarrytown Station or Philipse Manor Station, with Philipse Manor sitting just a 10-to-15-minute walk from Kingsland Point Park. Visitors arriving at Tarrytown Station can reach the park by ride-share or by walking up the RiverWalk, the pedestrian path that is also being extended to link the park with the neighboring Edge-on-Hudson development as part of a planned 51.5-mile trail network spanning 14 Westchester municipalities, according to the Sleepy Hollow Hotel's blog.
Kingsland Point Park itself is an 18-acre waterfront site built in 1926 as one of Westchester County's first county parks, owned by the county but managed directly by the Village of Sleepy Hollow, per Westchester County Parks. Sitting at the mouth of the Pocantico River, the park offers public overlooks facing the Sleepy Hollow Lighthouse and the Governor Mario M. Cuomo Bridge. The Sleepy Hollow Lighthouse was severely damaged in an arson and vandalism spree in 2025.
