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Halloween and 20 More Top Things To Do in Westchester and the Hudson Valley with Kids October 2025, from Mommy Poppins Editors

Join the Monster Party at Legoland's Brick-or-Treat this month. Photo courtesy of Legoland
Join the Monster Party at Legoland's Brick-or-Treat this month. Photo courtesy of Legoland
9/28/25 - By Katherine Dhurandhar

Halloween is the name of the game in October, which means Westchester and the Hudson Valley are alive with pumpkin patches, haunted houses, fall festivals, and of course trick-or-treating—there are so many opportunities to wear Halloween costumes!

From Oktoberfests to spooktacular celebrations, the region has standout events all month long, including the Sleepy Hollow Paddleboarding Witches Festival and the Tarrytown Halloween Parade. And don't miss taking a scenic train ride to a pumpkin patch on the Catskill Mountain Railroad's Pumpkin Express.  

Families can also enjoy spectacular pumpkin light shows throughout the month at the Westchester favorite Great Jack-o'-Lantern Blaze or at the site of the Woodstock Festival at Peace, Love & Pumpkins at Bethel Woods Center for the Arts. 

These are just a few of our favorite things to do in Westchester and the Hudson Valley this month—we're adding more events to the Westchester Events Calendar every day. 

More Things To Do in Westchester and the Hudson Valley:

OUR LATEST VIDEOS

Top Things to Do in Westchester and the Hudson Valley with Kids this October

Sleepy Hollow Glass Pumpkin Fundraiser

Sleepy Hollow–FREE
Thursday, October 2 - Sunday, October 5, 2025
The Village of Sleepy Hollow welcomes back the artists from the Adirondack Glassblowing Studio for the 4th annual Glass Pumpkin Patch Fundraiser in Kingsland Point Park. This festive event will showcase hundreds of whimsical, vibrantly colored glass pumpkins. READ MORE

Legoland's Brick-or-Treat Presents Monster Party

Goshen
Thursday, October 2 - Sunday, November 2, 2025
The Monster Party begins the moment you step into the park with a boo-tifully decorated entry arch. Meet Lego Monster characters like Spider Lady and Wacky Witch and make your way to the treat stations around the park. Don’t forget your costumes! READ MORE

Handcrafted Oktoberfest at Dutchess County Fairgrounds

Rhinebeck
Saturday, October 4-Sunday, October 5, 2025
This artfully reimagined Octoberfest is centered around the concept of handmade but also infused with harvest energy and Oktoberfest staples. Family activities include horse-drawn carriage rides, a petting zoo, pumpkin painting, a master pumpkin carver, giant pumpkin weigh-off, and more. READ MORE

Children's Day at Headless Horseman Hayrides

Ulster Park
Saturdays, October 4 and 18, 2025
On Children's Day, this hayride tones down the scare level. Music and other surprises make this the perfect outing for families with young children. READ MORE

Ridgetoberfest at Ridge Hill

Yonkers–FREE
Saturday, October 4, 2025
Enjoy an afternoon filled with family-friendly activities and exciting entertainment along Market Street and in Ridge Hill's newly renovated Park Plaza. Activities include live music, hayrides, face painting, and seasonal beer provided by Bronx Beer Hall. READ MORE

Peekskill Rotary Fall Festival

Peekskill–FREE
Saturday, October 4, 2025
The Rotary Club of Peekskill's annual fall festival features food, beer & wine trucks, craft and art vendors, a DJ, and musical acts. Children’s activities include pumpkin painting, a kids' maze, and inflatables.  READ MORE

Hudson Valley Apple Festival at Barton Orchards

Poughquag
Saturday & Sunday, October 4-5, 2025
Celebrate the heart of apple season at the Hudson Valley Apple Festival! Enjoy fresh apple picking, farm-favorite treats like cider donuts and apple cider, and a full weekend of family fun. Explore the Fun Park, hop on hayrides, get lost in the corn maze, and visit the barnyard animals. READ MORE

Family Fun Day at Untermyer Gardens

Yonkers
Sunday, October 5, 2025
This year's family fun day at Untermyer Gardens features a magic show in the amphitheater, animal ambassadors from the Nature Center at Greenburgh, and fun activities for kids, including a scavenger hunt, arts & crafts, and storytime.   READ MORE

Warwick Applefest

Warwick–FREE
Sunday, October 5, 2025
This festival features more than 150 craft vendors, more than 75 food vendors, four stages of live music, and an apple pie baking and eating contest. There's also a children's carnival, and Warwick stores are within easy reach for additional browsing. READ MORE

Eastchester Columbus Day Carnival and Parade

Eastchester–FREE
Friday, October 10-Monday, October 13, 2025
Eastchester goes all out Columbus Day weekend, with a four-day carnival, a holiday parade, and more. The carnival features lots of rides for all ages, games with prizes, vendors and exhibitors, and food. Time your visit around the schedule of live music, fireworks, and more.  READ MORE

Peace, Love & Pumpkins at Bethel Woods Center for the Arts

Bethel
Multiple dates, Friday, October 10-Sunday, November 2, 2025
View hand-carved jack-o'-lanterns and glowing pumpkin art as you walk the garden trails on the site of the Woodstock Festival. Exhibits include mermaids, dinosaurs, and Woodstock Festival icons. READ MORE

Sugar Loaf Fall Festival

Sugar Loaf–FREE
Saturday & Sunday, October 11-12, 2025
Art, crafts, food, and music are all on tap at the annual Sugar Loaf Fall Festival, plus family-friendly activities, including face painting, a petting zoo, bouncy houses, a kids zone, and a witches parade for a magical touch. READ MORE

Warwick Children's Book Festival

Warwick–FREE
Sunday, October 12, 2025
Join more than 70 distinguished, award-winning authors and illustrators to meet young readers and their families.  Adding to the festivities will be a free children's concert by The Uncle Brothers; face-painting by Pixie Pop; simple crafts for children to make and take home; and therapy dogs to listen to children read their new books aloud. READ MORE

Yorktown Fall Festival & Car Show

Yorktown Heights–FREE
Sunday, October 12, 2025
The Yorktown Chamber of Commerce invites visitors to this day-long festival featuring more than 150 vendors, plus children's rides and crafts, live musical and dance performances, food trucks, a beer garden, a senior lunch, 200+ car classic cars, and a Nathan's hot dog eating contest. READ MORE

Sleepy Hollow Paddleboarding Witches Festival

Sleepy Hollow–FREE
Sunday, October 12, 2025
The Paddleboarding Witches Festival features a costumed paddleboarding session followed by a party with food trucks, vendors, and a live telling of the Legend of Sleepy Hollow.  READ MORE

Hulda's Night at Rockefeller State Park

Pleasantville
Wednesdays-Saturdays, October 15-25, 2025
“Hulda’s Night” is a very special immersive theater experience that the Rockefeller State Park Preserve hosts once a year during the last two weeks of October. Audiences are led along Rockefeller’s famous carriage roads which are specially lit this night only by lanterns reminiscent of the age of Hulda – the time of the American Revolution. They may feel that they are walking back in time, as indeed they are. READ MORE

Halloween Weekend at the Westchester Children's Museum

Rye
Saturday, October 18-Sunday, October 19, 2025
Swing by the Westchester Children's Museum all Halloween weekend for Halloween-themed STEAM activities, including name 'dem bones, a glow-in-the-dark room, spider web engineering, ghost pour painting, and monster hide n' seek.  READ MORE

Catskill Mountain Railroad's Pumpkin Express

Kingston
Weekends, October 18-26, 2025
Take a spectacular journey along the former Ulster & Delaware Railroad corridor and see the natural beauty of the Catskills from the Catskill Mountain Railroad’s unique perspective aboard Ulster County’s only scenic train. Pumpkin Express trains travel the tracks to the Pumpkin Patch, where passengers will be able to select their favorite pumpkin to take home and decorate. READ MORE

Tarrytown Halloween Parade

Tarrytown–FREE
Saturday, October 25, 2025
This spooky spectacle of marchers and floats is back with costume and float-decorating contests. The parade begins in Patriot Park and ends at Main Street with a block party.  READ MORE

The Great Jack-o'-Lantern Blaze at Van Cortlandt Manor

Croton-on-Hudson
Multiple dates through Sunday, November 16, 2025
This renowned walk-through Halloween experience features more than 7,000 hand-carved, illuminated jack-o'-lanterns forming assorted impressive displays, with lighting and music enhancements. New for 2025 is a jack-o'-lantern big top adventure, a Wicked-themed, emerald-hued storybook pumpkin dreamscape, and the Headless Horseman’s Hideaway featuring spooky sips and haunting visits from the Horseman himself.  READ MORE

Places featured in this article:

Headless Horseman Hayrides and Haunted Attractions
City of Peekskill Riverfront Green
Bethel Woods Center for the Arts
Warwick Valley Middle School Gymnasium

About the Author

Katherine Dhurandhar
Katherine Dhurandhar is a Community Publisher for Mommy Poppins, representing the Westchester and Hudson Valley region of New York, and a freelance copyeditor for Westchester Publishing Company. In her free time, she enjoys hiking, camping, and traveling with her husband and son.
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