Fall & Halloween in Sleepy Hollow, NY

Fall Experiences

From riverside trails to hillside forests, the season is at its best out here.

Rockefeller State Park

Philipsburg Manor

Tarrytown Music Hall - Image credit shutterstock - David Garcia

Main Street Tarrytown

Old Croton Aqueduct Trail

Washington Irving's Sunnyside

Tarrytown Lakes Park

Lyndhurst Mansion

Westchester RiverWalk

Your Perfect Fall Weekend

Friday - Evening:

Check in, settle in. Take a walk down Tarrytown's Main Street. Head back to Hudson Bistro for light bites and spooky cocktails; a good first taste of the season.

Saturday - Morning:

Tash Farmers Market at Patriots Park: grab coffee, browse the stalls. Then pick up bikes from the hotel and ride Westchester RiverWalk along the Hudson or over the Governor Mario M. Cuomo Bridge.

Saturday - Afternoon:

Visit Sleepy Hollow Cemetery, walk the grounds, find Irving's grave, take it all in. Then a short drive to Washington Irving's Sunnyside for a daytime tour before it closes.

Saturday - Evening:

Head out to one of the season's big events: the Blaze, Irving's Legend, or Twilight Village. If your visit falls on October 24, make sure you don't miss the Tarrytown Halloween Parade.

Sunday - Morning:

Breakfast at Hudson Bistro. Then a morning hike at Rockefeller State Park, as the carriage roads are stunning in fall color.

Sunday - Late Morning:

Return to the hotel, unwind with a treatment at Hudson Spa, or take a swim in the pool. Head home when you're ready, or stay another night.

Spend Halloween in
Sleepy Hollow

The world's most legendary Halloween, right outside your door. From the parade to the Blaze, the Hudson Valley and Sleepy Hollow Halloween events calendar is unlike anywhere else.

Tarrytown Halloween Parade:

When you plan a Halloween trip to Sleepy Hollow, attending the Tarrytown Halloween Parade is a must. The annual parade steps off at 5pm from Patriot's Park on Broadway — the real Wiley's Swamp from the Legend. Floats, live music, costumes, and a block party on Main Street to follow. Free to watch; registration required to march. Viewing along the parade route is free.

Jack O'Lantern Blaze - Image by Teri Virbickis

The Great Jack O'Lantern Blaze:

See thousands of jack o'lanterns illuminate the night across the 18th-century riverside grounds of Van Cortlandt Manor. The Great Jack O'Lantern Blaze features an original soundtrack, synchronized lighting, and displays for all ages. Get your tickets here.

Sleepy Hollow Cemetery - Danita Delimont / Shutterstock

Sleepy Hollow Cemetery Tours:

One of the most storied burial grounds in America, 90 acres overlooking the Hudson, home to Washington Irving, Andrew Carnegie, and William Rockefeller. Explore the cemetery by kerosene lantern light on the Classic Evening Lantern Tour, or join a daytime guided walk through two centuries of history. Get your tickets here.

Tarrytown Music Hall - Jaclyn Vernace / Shutterstock

Ghost Tours at Tarrytown Music Hall:

Built in 1885, the Tarrytown Music Hall hosted the Rockefellers, Goulds, and Vanderbilts, and some of them may never have left. These guided "balcony to backstage" tours reveal the secrets of the theater, its history, and the ghostly guests who still linger. Get your tickets here.

Irving's Legend at Washington Irving's Historic Sunnyside Cottage:

Master storyteller Jonathan Kruk performs outdoors under the stars at Washington Irving's own Sunnyside estate, with live music and an appearance from the Headless Horseman himself. Come see why people return year after year. Get your tickets here.

Lyndhurst After Dark:

The candlelit Lyndhurst Mansion comes alive with Victorian lore and the darker side of Gilded Age history. Timed entry lets visitors experience the house decorated in the spirit of the season, with special collections on display relating to the superstitions of the age. Get your tickets here.

Twilight Village at Philipsburg Manor:

As evening settles over Philipsburg Manor, storytellers, fire performers, and legendary characters bring Irving's world to life. Wander through a pop-up market, grab food and drinks, and watch as the Headless Horseman makes a dramatic appearance in a sound-and-light spectacle. Expanded for 2026 with more characters and new performances, one of the most atmospheric events of the season. Get your tickets here.

Village of Sleepy Hollow - Maria Florencia Rossi / Shutterstock

Village of Sleepy Hollow Block Party and Hay Ride:

Two nights of community Halloween festivities in the heart of the village; live music, local vendors, and hayrides through the streets of Sleepy Hollow after dark. As one of the best Sleepy Hollow Halloween events to attend, this is the kind of local tradition that makes the town place feel different from every other Halloween destination. Get your tickets here.

Wicked Weeknight

Duis aute irure dolor in reprehenderit in voluptate velit
Excepteur sint occaecat cupidatat non proident, sunt in culpa
Ut enim ad minim veniam, quis nostrud exercitation
Consectetur adipiscing elit, sed do eiusmod tempor incididunt
Duis aute irure dolor in reprehenderit in voluptate velit
Excepteur sint occaecat cupidatat non proident, sunt in culpa
Ut enim ad minim veniam, quis nostrud exercitation
Consectetur adipiscing elit, sed do eiusmod tempor incididunt

BOOK NOW

Blogs

A Perfect Day in Sleepy Hollow: Where to Eat, Explore & Relax

Family-Friendly Fun in Westchester: Top Activities for All Ages

Old Dutch Church and Headless Horseman: Separating Fact from Fiction

Things to Do in Westchester County This November

Sleepy Hollow Halloween Run: What to Expect and Where to Stay

Explore the Best Halloween Events Near Sleepy Hollow, NY

In the Footsteps of Washington Irving: A Literary Tour of Sleepy Hollow

A Hauntingly Good Time: Halloween Festivities in Sleepy Hollow

Discover Lyndhurst Mansion: A Must-Visit Near Sleepy Hollow Hotel

Step Back in Time: The Story of Sleepy Hollow's Old Dutch Church

Ready to Meet the
Legend?

Fall weekends in Sleepy Hollow fill fast. Book your stay at Sleepy Hollow Hotel, a Dolce by Wyndham, and experience Hudson Valley's most extraordinary season.

Book Your Stay

Fall & Halloween
in Sleepy Hollow

Fall Experiences