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The 25 Best Things To Do with Westchester Preschoolers and Toddlers this Fall

Dalmatian Day at the FASNY Museum of Firefighting is fun for all. Photo courtesy of the museum
Dalmatian Day at the FASNY Museum of Firefighting is fun for all. Photo courtesy of the museum
9/11/22 - By Susan Miele

We’ve gathered up our favorite things to do with toddlers and preschoolers this fall in Westchester and the Hudson Valley. Whether they ride your shoulders while apple picking or rock out while wearing Halloween costumes and hanging with alpacas, we’ve got the makings of memories to help fill up those photo albums. As an added perk, many of these fall events are FREE!

For more options, check out our Event Calendar and our Fall Fun Guide for Westchester Kids.

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OUR LATEST VIDEOS

Budding Buddhas teaches a free yoga class with engaging songs and poses for toddlers.
Budding Buddhas teaches a free yoga class with engaging songs and poses for toddlers.

Things To Do with Westchester Toddlers and Preschoolers in September

Shake Your Sillies Out

Mamaroneck–FREE
Thursdays through October 27
This weekly program for toddlers features musical instruments, parachute play, nursery rhymes, and singing. READ MORE

Holy Trinity Greek Festival

New Rochelle
Thursday, September 15-Sunday, September 18
Expect traditional carnival features—rides, games, food—but with a strong presence of Greek influence: gyros, baklava, live Greek music, Greek dancing, and more. A flea market is also on the agenda. Opa!   READ MORE

Storybook Dancing with Steffi Nossen at the White Plains Public Library

White Plains
Thursday, September 15
Children embark on a storybook adventure, enhanced by music and dance. Led by an instructor from the Steffi Nossen School of Dance. READ MORE

Yoga Tots with Budding Buddhas

Tuckahoe
Thursday, September 15
The children's instructor from Budding Buddhas teaches a free yoga class for toddlers with a parent/caretaker. The classes incorporates traditional yoga poses, props and engaging songs to build motor skills, confidence and relaxation skills.  READ MORE

Creative Community Friday: Artful Families

Katonah
Friday, September 16
Families, friends, and neighbors gather for creative fun at the KMA on the 3rd Friday of each month. Spark the imagination of 2- to 5-year-olds with stories, artmaking, and gallery experiences inspired by the artworks on view.  READ MORE

Larchmont Day Fall Fest

Larchmont–FREE
Saturday, September 17
Celebrate Larchmont pride with a big bash in town. Highlights include live music, pumpkin decorating, a bouncy house, magic show, kids' games, and food & drinks. READ MORE

Sleepy Hollow Culture Festival

Sleepy Hollow–FREE
Saturday, September 17
This family-friendly festival celebrates the many cultures represented in Sleepy Hollow, with live music, folk dance, food vendors, free kids activities, crafts, and a magic show.  READ MORE

Family Free Night at the Mid-Hudson Discovery Museum

Poughkeepsie–FREE
Every third Saturday through December 17
Come in after-hours and explore all of the museum exhibits for free at family free nights at the Mid-Hudson Discovery Museum.  READ MORE

Armonk Cider & Donut Festival and 5K Run

Armonk–FREE
Sunday, September 18
Enjoy a variety of activities for families and, of course, doughnuts and cider. A pie-eating contest, doughnut fishing, live music, carnival rides, kids' races, a 5K, face painting, bouncy houses, and more are featured. READ MORE

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

Croton on Hudson
Friday, September 16-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. 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

Kites Over the Hudson

Newburgh–FREE
Saturday, September 24
Help paint the sky in vivid hues as you join other families in this annual kite-flying event. Complimentary kites are given to the first 150 participants ages 15 and younger. Entrance to the museum and tours of the historic site are also free on the day of the event. READ MORE

Dalmatian Day

Hudson
Saturday, September 24
Celebrate the return of FASNY’s Dalmatian Day. Activities include meeting live dalmatians, games with prizes, dalmatian-themed crafts, juggling show, puppet show, and more.  READ MORE
Pumpkinfest at Pine Island Tower Park is outdoor fun for the whole family. Photo courtesy of Pine Island NY Chamber of Commerce
Pumpkinfest at Pine Island Tower Park is outdoor fun for the whole family. Photo courtesy of Pine Island NY Chamber of Commerce

Things To Do with Westchester Toddlers and Preschoolers in October

Jay Day

Rye
Saturday, October 1
Celebrate American culture with live music, book signings, face painting, hands-on art and planting activities, pony rides, historical house tours, balloon twisting, and geocaching with prizes. Purchase items from craft vendors, including old-fashioned silhouette portraits and vintage maps.  READ MORE

Warwick Applefest

Warwick–FREE
Sunday, October 2
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

Pine Island Pumpkinfest

Pine Island
Monday, October 10
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

Chappaqua Children's Book Festival

Chappaqua–FREE
Saturday, October 15
Meet children’s book authors and illustrators, and enjoy readings, signings, and assorted activities at the return of this annual festival. This year's festival is the largest yet, with 180 renowned children's book authors and illustrators participating. Mary Pope Osborne, author of the Magic Treehouse series, is headlining this year.  READ MORE

Pumpkin Painting/Carving

Yorktown
Saturday, October 15
Select a pumpkin from the patch and decorate it however you please. Little ones will paint, older kids can carve and everyone will get creative.  READ MORE

NY Sheep and Wool Festival

Rhinebeck
Saturday, October 15-Sunday, October 16
Attractions at the New York Sheep and Wool Festival include sheep shows, vendors, crafts, frisbee dogs, and a petting zoo.  READ MORE

Fall Family Fun Fest at the Ashokan Center

Olivebridge
Sunday, October 16
The fall festival at the Ashokan Center features fresh apple cider pressing, pumpkin painting, broommaking, hayrides, live music, seasonal food, guided hikes, and fun for all ages. READ MORE

Fall Festival

Scarsdale
Saturday, October 22-Sunday, October 23
Kick off the fall season at Greenburgh Nature Center’s Fall Festival. Enjoy family-friendly activities like a pumpkin and scarecrow walk, live music, crafts and games, a scavenger hunt, apple cider demonstrations and tastings and more. READ MORE

A Very Fluffy Halloween with Alpacas

Multiple days in October - Pleasant Valley
Join this fluffy spooky celebration with alpacas and goats in Halloween costumes. Costumes are encouraged.  READ MORE
Start off the holiday season with the New Rochelle Thanksgiving Day Parade. Photo courtesy of the event
Start off the holiday season with the New Rochelle Thanksgiving Day Parade. Photo courtesy of the event

Things To Do with Westchester Toddlers and Preschoolers in November

Holiday Train Show at Greenburgh Nature Center

Scarsdale
Weekends from Saturday, November 12-Sunday, December 4
The Holiday Train Show returns to the Greenburgh Nature Center for four weekends, featuring a special 12-foot-by-18-foot display of model trains traveling through countryside scenes. READ MORE

The Music of Bob Marley for Kids at Garcia's at the Capitol Theatre

Port Chester
Saturday, November 19
The Rock and Roll Playhouse and Garcia's at The Capitol Theatre invite kids to rock out while learning about classic styles of popular music through games, movement, and stories. The music of Bob Marley is featured at this Earth Day Celebration. READ MORE

Annual New Rochelle Thanksgiving Parade

New Rochelle–FREE
Thursday, November 24
The city of New Rochelle hosts its 60th annual Thanksgiving Day Parade, featuring giant parade balloons, marching bands, floats, vintage cars, dancers, singers, and marchers from local colleges, schools, and more. The parade is reportedly the largest parade in New York outside of the Macy's Thanksgiving Day Parade in NYC.   READ MORE

Rodgers and Hammerstein's Cinderella

Yorktown
Select dates in November
Enjoy this stage adaptation of the classic movie Cinderella by the players at the Yorktown Stage.  READ MORE

Places featured in this article:

Holy Trinity Greek Orthodox Church
Washington's Headquarters State Historic Site