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Columbus Day Weekend in Westchester and the Hudson Valley: Best Things To Do

The Pine Island Pumpkinfest, where you can decorate a pumpkin for Halloween, is a Columbus Day tradition. Photo courtesy of the Pine Island Chamber of Commerce
The Pine Island Pumpkinfest, where you can decorate a pumpkin for Halloween, is a Columbus Day tradition. Photo courtesy of the Pine Island Chamber of Commerce
10/11/24 - 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 14, 2024, with tons of fun things to do. Special events held only on Monday include Kids' Day at Kevin McCurdy's Haunted Mansion and Pine Island's Pumpkinfest. 

Families can enjoy the festivities all weekend, including Monday, at Wappingers' Carni "Fall" and Legoland New York's Monster Party. In honor of Indigenous Peoples' Day, learn about some of the original inhabitants of the Westchester area at a Lenape Indigenous Peoples' Day presentation at the historic St. Paul's Church.  

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

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

Eastchester Columbus Day Carnival and Parade

Eastchester–FREE
Friday, October 11-Monday, October 14
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

Carni "Fall" Parade and Festival in Wappingers Falls

Wappingers Falls–FREE
Friday, October 11-Monday, October 14
Wappinger's Carni"fall" is a four-day Columbus Day weekend celebration with fire performers, carnival rides, live music, food trucks, games and activities, a parade, and fireworks.  READ MORE

Trick or Treat at Hilltop Hanover Farm

Yorktown Heights–FREE
Saturday, October 12
Visit the animals and explore the historic sites of Hilltop Hanover Farm as you trick-or-treat at the barn doors. Treats will be available while supplies last; costumes are encouraged! READ MORE

Soukup Farms Harvest Festival

Dover Plains
Saturday, October 12-Monday, October 14
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

Pumpkin Picking Autumn Celebration at Muscoot Farm

Katonah
Saturday, October 12-Monday, October 14
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

Oktoberfest at Bear Mountain State Park

Bear Mountain–FREE
Saturday & Sunday, October 12-13
Experience the excitement of NY’s largest free Oktoberfest at the beautiful Anthony Wayne Recreation Area! The annual Bear Mountain Oktoberfest is your go-to destination for authentic Bavarian traditions, including fantastic beer, lively music, and traditional German food. Let the kids enjoy the bouncy slide and house and revel in live music performances, face painting, and much more! READ MORE

Warwick Children's Book Festival

Warwick–FREE
Sunday, October 13
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
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
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

Nyack Famous Street Fair

Nyack–FREE
Sunday, October 13
The Nyack Famous Street Fair is set to take place on October 13, 2024, from 10am to 5pm. This event will be held on Main Street and Broadway in Downtown Nyack. Expect over 300 exhibitors offering a variety of arts, crafts, retail items, gifts, and festival foods. There will also be live music and outdoor cafes, making it a fun event for the whole family. READ MORE

A Very Fluffy Halloween at Lilymoore Farm

Pleasant Valley
Opening weekend Saturday & Sunday, October 12-13
It’s a Halloween fest – only way cuter. Meet fluffy alpacas and llamas strutting their stuff in lion’s manes, rainbows, or even as a butterfly. It’s the perfect blend of cuteness and hilarity—who wouldn’t want a selfie with an alpaca dressed as a hippie? READ MORE

Pine Island Pumpkinfest

Pine Island
Monday, October 14
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

The Lenape: Indigenous Peoples' Day Presentation at St. Paul's Church

Mt Vernon–FREE
Monday, October 14
Celebrate Indigenous Peoples' Day by learning about some of the original inhabitants of Mt Vernon, the Lenape. Dr. Eugene Boesch, author and archaeologist, explores the Lenape people's history, culture, and legacy at St. Paul's Church.  READ MORE

Columbus/Indigenous Peoples' Day at Weed Orchards & Winery

Marlboro
Monday, October 14
At this family-friendly event, the playground will be open, tractor rides begin at noon, and the farm allows friendly, leashed dogs on the property.  READ MORE

Kids' Day at Kevin McCurdy's Haunted Mansion

Wappingers Falls
Monday, October 14
This is a special show for younger kids that won't give them nightmares. Kids' day entertainment includes magic shows and activities like trick-or-treating with friendly monsters. READ MORE

Fall Harvest Celebration at Kelder's Farm

Kerhonkson
Every weekend in October plus Monday, October 14
Celebrate the fall harvest at Kelder's Farm and enjoy scenic fall colors, apple and pumpkin picking, a corn maze, and all the farm attractions, including a giant jumping pillow, mini-golf, tube slides, farm animals, and games. Food and drinks are also available, including a taproom for adults. READ MORE

Harvest Hunt at Locust Grove Estate

Poughkeepsie
Weekends through October 20 plus Monday, October 14
Come find more than 30 decorated pumpkins and whimsical photo-ops hidden among the flowers and trees on a Locust Grove scavenger hunt/story walk. Costumes are encouraged. Bring a picnic and enjoy under the trees! READ MORE

Legoland's Brick-or-Treat Presents Monster Party

Goshen
Weekends through Sunday, October 27, plus Monday October 14
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

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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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