Westchester County Fall Foliage and Harvest Festivals

Take a fall foliage driving tour, then see the Great Jack O’ Lantern Blaze at harvest festivals in Westchester County.


When the postcard-perfect fall foliage peaks in October, our family sets out for a drive to Westchester County, which lies just north of New York City. The county is part of bucolic Hudson Valley, the setting for favorite childhood fables like Rip Van Winkle and The Legend of Sleepy Hollow, a town which especially comes alive each Halloween season. 

Fall Foliage Drives

There are multiple byways that criss-cross Westchester County, providing a colorful selection to create your own leaf-peeping driving tour. Head north out of New York City and along Route 22 you’ll pass backroads and village centers, horse farms and estate homes. Farther west, Route 9 strings several small towns together along the Hudson River. We like to stop for lunch in Tarrytown, where sweet potato fries lure us to Horsefeathers. Head toward the Bear Mountain Bridge on Route 202, and you’ll find places to park for a panoramic view of the river. 

You can leave the route planning to the experts by following the Fall Foliage Driving Tours recommended by the Westchester County Office of Tourism

Outdoor Kids Activities

In Westchester, there’s no shortage of open space and outdoor activities to expose kids to the energizing fall air. Seasonal hayrides are a highlight at Muscoot Farm in Somers. Children visit with the animals, clamber over tractors, learn how to build scarecrows, hike on guided fall foliage tours or participate in a Halloween scavenger hunt.

Kids can learn that pumpkins grow from vines, not at the supermarket. Pick your own at the Outhouse Orchards in North Salem, along with a variety of crispy apples. Our kids know their efforts will be rewarded with a freshly baked cider donut.

Where there are apples, there’s cider. Watch it being pressed at Thompson’s Cider Mill in Croton-on-Hudson. Several tasty apple varieties, including heirlooms grown on-site, combine to create a pure, old-fashioned beverage.


Westchester’s Fall Festivals-o-Ween

‘Tis the season for festivals. We like the folksy vibe of the Harvest Festival at the Stone Barns Center for Food & Agriculture in Pocantico Hills, taking place this Sunday, Oct. 4. Tickets cost $30 for adults, $20 for kids 6 to 14, $10 for kids 2 to 5 and free for kids under 2. Act fast: Sales end Oct. 3.

The Annual Fall Festival at Teatown Lake Reservation, being held Oct. 18 in Ossining, connects kids with nature, offering eco-crafts and birds of prey demonstrations. Tickets cost $8 for adults, $5 for kids.

Westchester is building a reputation for distinctive Halloween events held at historic sites across the county. There really is a village called Sleepy Hollow, and it’s here. Every October, The Legend of Sleepy Hollow comes to life during the Legend Weekend at Washington Irving’s former home, Sunnyside, and the nearby 18th century Philipsburg Manor. Daytime activities are geared toward kids: pumpkin carving, puppet shows, scarecrow making and woodland walks. In the evening, a spine-tingling re-enactment of The Legend brings the Headless Horseman thundering through the pasture on a black stallion. This year’s event takes place the weekends of October dates: 18 and 19, and 25 and 26. Reserve tickets online or by calling. 914-631-8200.

One of the most artistic and engaging events we’ve experienced is The Great Jack O’ Lantern Blaze, a spellbinding display of 4,000 glowing jack-o’-lanterns, which takes over the 17th century Van Cortlandt Manor in Croton-on-Hudson. It takes an hour to walk along the path leading to the stone Manor House, past the heritage gardens, down to the Ferry House and alongside the Croton River. Look in any direction and you’ll see jack- o’-lanterns—hanging from tree limbs, perched on rooftops and staged in themed vignettes, including an undersea aquarium, a hillside spider web, a scarecrow avalanche and a field of intricate Celtic knots.

Candlelight intensifies the magic of characters—ghosts, snakes, dinosaurs, fish—all born from pumpkins. Add spooky music and sound effects, and it’s a multi-sensory experience. The Blaze takes place each weekend in October and costs $15 for adults, $10 for kids 5 to 17, free for kids under 5. Reserve tickets online at or by calling 914-631-8200.  

Destinations: New York, Westchester County

Themes: Family Travel, Outdoor Adventures

Activities: Hiking, Arts and Entertainment, Sightseeing

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