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Columbus Day Weekend in Westchester: Best Things To Do with Kids

An annual Columbus Day tradition, the Pine Island Pumpkinfest, features tons of kid-friendly activities. Photo courtesy of Pine Island Chamber of Commerce
An annual Columbus Day tradition, the Pine Island Pumpkinfest, features tons of kid-friendly activities. Photo courtesy of Pine Island Chamber of Commerce
9/5/22 - By Katherine Dhurandhar

Looking for the best things to do in Westchester and the Hudson Valley over the long Columbus Day weekend? We've got tons of family-friendly events to add to your list.

Whether you call the holiday Columbus Day or Indigenous Peoples Day, we're celebrating the day off on Monday, October 10 with tons of fun things to do. The long weekend makes a great jumping-off point for Halloween celebrations, beginning with the G-rated Headless Horseman Haunted Children's Day on Saturday. Enjoy pick-your-own fun at Seed Song Farm's weekend-long Pumpkins and Sunflowers Harvest Fest, and save some energy for a trip to the popular Eastchester Columbus Day Parade on Monday.

We've got tons more seasonal picks on our list of the best Halloween events in Westchester and the Hudson Valley, and you can find more things to do any day on our Family Activity Calendar.

And don't miss your chance to win! Mommy Poppins is sponsoring a pretty amazing giveaway: The grand-prize winner will get a 2 night all-inclusive trip for 2 adults and 2 children (including airfare from the continental US, food, & beverages) to Velas Vallarta family resort in Puerto Vallarta, Mexico. Enter to win our Family Fun Resort Getaway. 

More Things To Do in Westchester and the Hudson Valley this Week with Kids:

OUR LATEST VIDEOS

Boo-gie down to a groovy monster soundtrack and disco takes over Legoland's Dragon Coaster. Photo courtesy of Legoland
Boo-gie down to a groovy monster soundtrack and disco takes over Legoland's Dragon Coaster. Photo courtesy of Legoland

Things To Do this Weekend in Westchester and the Hudson Valley with Kids

Eastchester Columbus Day Carnival and Parade

Eastchester–FREE
Friday, October 7-Monday, October 10
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

Artist Talks and Teen Workshop: Alicia Gibson

Larchmont–FREE
Saturday, October 8
Come and create with One River School at this free exhibition and teen workshop featuring artist Alicia Gibson. Participants can meet other local artists and create new works alongside them. Bring home fantastic art, attend a Q and A with a working contemporary artist, and shop and browse the artwork for sale. READ MORE

Soukup Farms Harvest Festival

Dover Plains
Saturday, October 8-Monday, October 10
Hit the pumpkin patch, hitch a hayride, and visit the exotic animals of the Two-by-Two traveling animal exhibit (on select dates) at 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

Pumpkin Picking Autumn Celebration

Katonah
Saturday, October 8-Monday, October 10
Join Muscoot Farm for Columbus Day weekend. The farm celebrates the fall season with a pumpkin picking and hayride fundraiser. You can also source the perfect pumpkin from its garden. READ MORE

Headless Horseman Haunted Attractions Children's Day

Ulster Park
Saturdays October 8 and 22
On Children's Day, the Headless Horseman Haunted Attractions tone down the scare level. Kids can enjoy a hayride and visit friendly characters along the way, in addition to the Magic Moon Maze, Haunted Gardens, Witch Hazel's Halloween House, and the Dinosaur Trail. Music and other surprises make this the perfect outing for families with young children. READ MORE

Yorktown Fall Festival & Car Show

Yorktown Heights–FREE
Sunday, October 9
The annual fall festival returns in a new location at the Jefferson Valley Mall. Family-friendly activities include inflatables, games, a pumpkin patch, arts and crafts, a dog costume parade, vendors, and food trucks. READ MORE

Mad Dash

Rhinebeck
Sunday, October 9
Support Mad River Trails during this fun and fundraising run. This charity event features a kids' run, a 5K walk/run, and a 10K. The Mad Dash is a fall favorite for hundreds of people! Enjoy the beautiful wooded and open trails at Harwood High, plus food and live music. READ MORE

JCC Mid-Westchester Fall Fest

Scarsdale–FREE
Sunday, October 9
The JCCMW opens its doors for a day of performances, food, and special family-friendly programming, including gymnastics and ballet showcases, family swim time, scuba lessons, story time, singalongs, and more.  READ MORE

Guided Hike

Mount Kisco–FREE
Sunday, October 9
See Westmoreland like never before and learn about the diverse, native wildlife and vibrant ecosystems. All hikes meet in the Nature Center and are guided by a professional naturalist. READ MORE

Pumpkinfest

Pine Island
Monday, October 10
This annual Columbus Day tradition features a bouncy house, pumpkin painting, face painting, games, crafts, touch-a-tractor, refreshments, and more. Attendees can enjoy food, ice cream, and tasty treats from on-site vendors.  READ MORE

Collage Workshop with Michael Albert

Rye–FREE
Monday, October 10
The Westchester Children's Museum invites kids for this workshop with Michael Albert, a nationally known pop artist. Kids can create their own collage art under Albert's watchful, creative eye. READ MORE

Community Adventure Play Experience (CAPEs)

Rye–FREE
Monday, October 10
Hosted by Sarah Lawrence College's Child Development Institute, in conjunction with the Westchester Children's Museum, Community Adventure Play Experiences (CAPEs) provide children and their caregivers the opportunity to enjoy self-directed play using natural, reusable, and recycled materials. READ MORE

The Legend Cirque

Sleepy Hollow
Fridays, Saturdays, and Sundays through Sunday October 16
Step back in time to the 1800s and hear the clamoring metal horseshoes click across cobblestone roads in this dark Sleepy Hollow tale. The Legend is the new, simmering adaptation of Washington Irving's iconic ghost story, "The Legend of Sleepy Hollow." The audience is treated to a cirque/theatre noir production with narration by Washington Irving in hologram form, commemorating the 200-year anniversary of, “The Legend of Sleepy Hollow!”  READ MORE

Pumpkins & Sunflowers Harvest Festival

Kingston
Weekends through Sunday, October 30
Pick your own pumpkins and sunflowers on weekends in October. Admission includes a small pumpkin or sunflower. Additional activities include a sunflower maze, flower picking, meeting farm animals, live music, hay rides, and baked goods.   READ MORE

Halloween Drive-Thru

Yonkers
Daily through Monday, October 31
Hop in the car for a seasonal drive-thru, with farm animal-themed displays through the end of September and Halloween excitement starting October 1. View more than a dozen scenes with inflatable characters and decorations, and tune the car’s radio to hear Clover the Cow’s spooky Halloween soundtrack.  READ MORE

Legoland's Brick-or-Treat Presents Monster Party

Goshen
Weekends through Sunday, October 30
Legoland New York goes all-out for Halloween, with costume contests, dance parties, live entertainment, characters, and trick-or-treating. The event is included with the price of admission. READ MORE

Legoland Discovery Center's Brick or Treat Monster Party

Yonkers
Daily through Tuesday, November 1
Ready for a bricktastic family adventure? Jump into a world of supercharged creativity, color, and playful learning at Legoland Discovery Center Westchester at Ridge Hill Mall. The ultimate indoor Lego playground invites guests to get into the Halloween spirit with spooky activities and a brand new 4D Halloween movie, The Great Monster Chase! READ MORE

The Great Jack-o'-Lantern Blaze

Croton-on-Hudson
Daily through Sunday, November 20
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. See the pumpkin carousel, windmill, and the New York City skyline. New for 2023, see an animated Ferris wheel and a jack-o'-lantern ode to circus sideshows. READ MORE

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