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

The Pine Island Pumpkinfest is a Columbus Day tradition. Photo courtesy of Pine Island Chamber of Commerce
The Pine Island Pumpkinfest is a Columbus Day tradition. Photo courtesy of Pine Island Chamber of Commerce
10/4/23 - 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 9, 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.

Families can enjoy the festivities all weekend, including Monday, at Bear Mountain's Oktoberfest, Wappingers' Carni"fall", and the Eastchester Columbus Day Carnival and Parade. 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.  

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.

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

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Pumpkin World in Pomona features hand-carved pumpkin art sculptures. Photo by the author
Pumpkin World in Pomona features hand-carved pumpkin art sculptures. Photo by the author

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 6-Monday, October 9
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

Wappingers Falls–FREE
Friday, October 6-Monday, October 9
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

Soukup Farms Harvest Festival

Dover Plains
Saturday, October 7-Monday, October 9
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

Katonah
Saturday, October 7-Monday, October 9
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

Children's Day at Headless Horseman Hayrides

Ulster Park
Saturdays October 7 and 21
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

Pound Ridge Harvest Festival

Pound Ridge–FREE
Saturday, October 7
Expect fun for all ages at this annual festival, including live music, a beer garden, and food trucks. Fun for kids includes a root beer garden, face painting, a haunted house, laser tag, pumpkin decorating, games, rides, and contests. READ MORE

Warwick Children's Book Festival

Warwick–FREE
Saturday, October 7
Join fellow readers to celebrate children’s literacy, share a love of the written word, discover new books, talk with those who create them, and have your book purchases autographed. READ MORE

Herb Fair & Market

Katonah–FREE
Saturday, October 7
Enjoy a day full of demonstrations and workshops by renowned herbalists, craftspeople, and horticulturists, as well as engaging children’s activities hosted by the Rye Art Center. READ MORE

Yorktown Fall Festival

Yorktown Heights–FREE
Sunday, October 8
Enjoy 150+ vendors, children's rides & crafts, live musical performances & dance Performances, food trucks & a beer garden, a senior lunch, a 200+ car classic car show, and a Nathan's hot dog eating contest. READ MORE

Cornwall Fall Festival

Cornwall–FREE
Sunday, October 8
The 51st annual fall festival returns to downtown Cornwall. Main Street is closed down and filled with vendors, food, and entertainment.  READ MORE

Pumpkinfest

Pine Island
Monday, October 9
Celebrate the local harvest of pumpkins and spend the day outdoors enjoying the warm sunshine and crisp fall air. This annual tradition features pumpkin painting, face and henna painting, a children’s bouncy house, yummy food, and touch-a-tractor.  READ MORE

The Lenape: Indigenous Peoples Day Presentation

Mt Vernon–FREE
Monday, October 9
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.   READ MORE

Oktoberfest at Bear Mountain

Bear Mountain–FREE
Weekends through October 21, plus Monday, October 9
Celebrate German culture at Bear Mountain's Oktoberfest, with activities for all ages including live music, dancing, games, a bounce castle with air slides, and pony rides, weather permitting. Plus enjoy all the usual Bear Mountain activities including the zoo, carousel, and hiking trails.  READ MORE

Fall Harvest Celebration

Kerhonkson
Every weekend in October plus Monday, October 9
Celebrate the fall harvest at Kelder's Farm, featuring scenic fall colors, apple and pumpkin picking, and all the usual 30+ farm attractions, including a giant jumping pillow, mini-golf, tube slides, farm animals, and tons of games. Food and drinks are also available, including a taproom for adults. READ MORE

Harvest Story Walk and Scavenger Hunt

Poughkeepsie
Every weekend in October plus Monday, October 9
Search the estate for more than 20 decorated pumpkins hidden among the flowers and trees while learning about the people who lived and worked at the historic estate in the year 1901. Participants can choose a time to come, tour at their own pace, and stay all day if desired. So, don your costumes, bring a picnic, and enjoy the day! READ MORE

Legoland's Brick-or-Treat Presents Monster Party

Goshen
Weekends through Sunday, October 29
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

The Great Jack-o'-Lantern Blaze

Croton-on-Hudson
Daily through Sunday, November 19
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

Pumpkin World

Pomona
Wednesdays-Sundays through October 31
Pumpkin World is an interactive family-friendly fall extravaganza featuring a 45-minute jack-o'-lantern trail illuminated with intricately hand-carved pumpkin art sculptures. The festival also includes a whimsical Pumpkin Village offering more fall fun for the whole family to enjoy with music, games, merchandise, and thrilling pumpkin-carving competitions by master artists. READ MORE

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