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27 Best Things To Do in Westchester and the Hudson Valley October 2024 with Kids

Get your costume ready for Cross County Center’s Halloween Spooktacular. Photo courtesy of the shopping center
Get your costume ready for Cross County Center’s Halloween Spooktacular. Photo courtesy of the shopping center
9/29/24 - 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. Families can 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. 

Find more top October fun in our Westchester and Hudson Valley Fall Fun Guide. 

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

Boo Arrow Farm Haunted Hayride

Pine Island
Select Days, October 2-30, 2024
Blue Arrow Farm celebrates Halloween with a pair of fun and frightful attractions. Families with wee ones should attend early in the evening for a not-so-spooky family train ride. After dark, the Boo Arrow Farm turns into a frightfully haunted hayride. Stick around for live music, vendors, face painting, and other fun. READ MORE

Handcrafted Oktoberfest at Dutchess County Fairgrounds

Rhinebeck
Saturday, October 5-Sunday, October 6, 2024
This artfully reimagined Octoberfest returns to Rhinebeck for its fifth anniversary. Produced by Quail Hollow Events, the festival 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, and dancing to live music. READ MORE

Children's Day at Headless Horseman Hayrides

Ulster Park
Saturdays, October 5 and 19, 2024
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

Jeff Boyer's Big Bubble Bonanza at the Paramount Hudson Valley Theater

Peekskill
Sunday, October 6, 2024
Bubble rainbows with people inside. Audience members making volcano bubbles! Gigantic bubbles that blow their own bubbles? See the newest, funniest, zany spectacular from world-famous, Guinness Book of World Records-holding, master bubble wrangler Jeff Boyer, as he takes bubbles to the max with big bubble flair. READ MORE

Warwick Applefest

Warwick–FREE
Sunday, October 6, 2024
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 11-Monday, October 14, 2024
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
Friday, October 11-Sunday, October 27, 2024
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

Warwick Children's Book Festival

Warwick–FREE
Sunday, October 13, 2024
Join Albert Wisner Public Library and more than 65 authors and illustrators at Stanley-Deming Park in Warwick, NY, on Sunday, October 13. Book lovers young and young at heart are invited to celebrate children's literature. READ MORE

Yorktown Fall Festival & Car Show

Yorktown Heights–FREE
Sunday, October 13, 2024
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 13, 2024
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

Pine Island Pumpkinfest

Warwick
Monday, October 14, 2024
Celebrate the local harvest of pumpkins and spend the day outdoors enjoying the warm sunshine and crisp fall air. The day features pumpkin painting, face and henna painting, a children's bouncy house, touch-a-tractor, firetruck, entertainment, crafts, games, activities, refreshments, and many exciting surprises. READ MORE

Open House at Lamont-Doherty Earth Observatory

Palisades–FREE
Saturday, October 19, 2024
Whether your child is an aspiring young scientist or a long-time science enthusiast, they are sure to enjoy Lamont-Doherty’s Open House. Tour the labs, participate in hands-on earth science activities with scientists, and learn from world-renowned researchers about their latest discoveries. READ MORE

Ridgetoberfest at Ridge Hill

Yonkers–FREE
Saturday, October 19, 2024
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

NY Sheep and Wool Festival

Rhinebeck
Saturday, October 19-Sunday, October 20, 2024
Attractions at the New York Sheep and Wool Festival include sheep shows, vendors, crafts, frisbee dogs, and a petting zoo.  READ MORE

Village of Mamaroneck Spooktacular Sunday

Mamaroneck–FREE
Sunday, October 20, 2024
The Village of Mamaroneck and Mamaroneck Chamber of Commerce invite you to grab your trick-or-treat bag, dress up as your favorite character, and join the Annual Spooktacular Halloween parade and festivities. READ MORE

Beacon Sloop Club Pumpkin Festival

Beacon–FREE
Sunday, October 20, 2024
Dedicated to promoting environmental and social issues, the Beacon Sloop Club hosts this festival offering kids' activities, a performance by the Rejuvenary River Circus, live music on two stages, and sails on the sloop Woody Guthrie. Pumpkin-themed cuisine is available for purchase. READ MORE

Ragamuffin Halloween Parade & Festival at Chappaqua Train Station

Chappaqua–FREE
Sunday, October 20, 2024
Put on your best costume and get ready to parade around Chappaqua at this festive celebration. Kids can enjoy inflatables, music, and activities after the Halloween costume parade.  READ MORE

Cross County Center Halloween Spooktacular

Yonkers–FREE
Saturday, October 26, 2024
Families can enjoy arts & crafts, a DJ dance party, inflatables, Hocus Pocus witches performance, a wizard magic show, spooky selfie spots, and more! READ MORE

The Little Mermen: The Ultimate Disney Tribute Band at Sugarloaf Performing Arts Center

Chester
Saturday, October 26, 2024
Recognized globally as the #1 Disney tribute band by Disney, Broadway.com, ABC News, and multiple other outlets, The Little Mermen brings Disney’s beloved songs to life with a rockin’ twist! The Little Mermen are known for their high-energy performances, dazzling costumes, and a setlist that spans a century of Disney’s iconic soundtracks. READ MORE

Tarrytown Halloween Parade

Tarrytown–FREE
Saturday, October 26. 2024
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

MyKingstonKids Halloween Fest & Parade

Kingston–FREE
Saturday, October 26. 2024
Prepare for an out-of-this-world adventure at the MyKingstonKids Halloween Fest with a Space Theme! Blast off into a galaxy of spooky fun where children can explore alien worlds, encounter extraterrestrial creatures, and embark on interstellar quests. Dress up in your best space gear and join us for a day of cosmic delights, featuring thrilling space-themed workshops, interactive activities, and a galaxy of treats!  READ MORE

Halloween Weekend at the Westchester Children's Museum

Rye
Saturday, October 26-Sunday, October 27, 2024
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

Nyack Halloween Parade

Nyack–FREE
Saturday, October 26, 2024
Put on your best costume and come out for one of the biggest Halloween parades in the area. The parade moves through downtown Nyack with float contests and costume contests for kids and adults.  READ MORE

Walktoberfest at Walkway over the Hudson

Poughkeepsie–FREE
Saturday & Sunday, October 26-27, 2024
More than 100 vendors await offering shopping, dining, and children's activities at this two-day event. Expect pumpkin painting, art projects, sand art, karate demos, princess character appearances, a dance performance, Home Depot construction kits, and more. Enjoy the view! READ MORE

Halloweekend at the Hudson River Museum

Yonkers
Saturday & Sunday, October 26-27, 2024
Trick or treat at the Hudson River Museum! Meet some creepy crawly critters at a live animal show presented by Greenburgh Nature Center. Plus: explore a haunted historic home on a Gothic Glenview Tour, learn about the stars in a planetarium show, and create a Spooky Silhouette in Family Art Workshops. READ MORE

Soukup Farms Harvest Festival

Dover Plains–FREE
Every weekend in October, plus Columbus Day 2024
Hit the pumpkin patch, hitch a hayride, and visit the exotic animals of the Two-by-Two traveling animal exhibit (on select dates) at the Soukup Farms Harvest Festival. There's also a climbable hay dragon, tractor exhibits, and a corn maze. Re-energize with a farm-to-table lunch. READ MORE

Legoland's Brick-or-Treat Presents Monster Party

Goshen
Fridays - Sundays throughout October 2024
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

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

Croton-on-Hudson
Daily in October 31 plus additional dates in September and November 2024
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 2024, celebrate the Blaze's 20th year with a giant birthday cake and Celebration Arch, check out the Gourd & Goblet Tavern, a new VIP experience on the pumpkin trail, and spot the giant Kraken rising from the Croton River. READ MORE

Places featured in this article:

Headless Horseman Hayrides and Haunted Attractions
Bethel Woods Center for the Arts
Lamont-Doherty Earth Observatory
Beacon Sloop Club and Riverfront Park
Chappaqua Train Station Parking Lot
Sugar Loaf Performing Arts Center
Downtown Nyack