The pie eating contest is just the start of the fun at the Armonk Cider and Donut Festival. Photo courtesy of the festival
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The Great Jack-o'-Lantern Blaze in Van Cortlandt Manor is a must-do Halloween event in the tri-state area. Photo courtesy of the Historic Hudson Valley
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Outhouse Orchards Corn Maze. Photo by Matt Nighswander
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Pick from a number of apple varieties at Hudson Valley orchards. Photo by Leslie Seaton via Flickr
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Enjoy glorious views on the Walkway Over the Hudson. Photo by Fred Schaeffer/courtesy of the Walkway.
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Kids can run, swing, slide, and even make music at Sally’s Dream Playground in Montgomery. Photo by Katherine Dhurandhar
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The Play Place in Elmsford is one of Westchester's top indoor play spaces.
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Roam the the cedar walk and gardens at Caramoor for a free, fun outing. Photo by Gabe Palacio
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Enjoy water sports at Westchester Summer Day in Mamaroneck. Photo courtesy of the camp
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Palisade Center's Climbzone features themed rock walls as high as 40 feet. Photo courtesy of Climbzone.
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Kids explore the great outdoors Hudson Highlands Nature Center. Photo courtesy of the center
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Kids under 1 are FREE hours at the Westchester Children’s Museum. Photo courtesy of the museum
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Kids can peek into the marine life in the aquariums at the Marine Education Center in Mamaroneck. Photo by Susan Miele
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Book your tickets now if you want to see the annual spectacle that is The Great Jack O'Lantern Blaze at Van Cortlandt Manor. Photo by the author
Book your tickets now if you want to see the annual spectacle that is The Great Jack O'Lantern Blaze at Van Cortlandt Manor. Photo by the author
8/29/25 - By Katherine Dhurandhar

Labor Day kicks off September activities, launching Westchester and the Hudson Valley's season of apple picking, fall festivals, pumpkin patches, and corn mazes.

The start of fall festivities includes the Armonk Cider & Donut Festival and the Port Jervis Fall Foliage Festival. To get in the Halloween spirit early, check out the Great Jack O'Lantern Blaze in Croton-on-Hudson, which features more than 7,000 hand-carved and lit-up pumpkins. And don't miss the return of the dazzling Flip Circus at the Jefferson Valley Mall. 

These are just a few of our favorite things to do in Westchester and the Hudson Valley this month—we're adding more events to the Westchester Events Calendar every day. 

More Things To Do in Westchester and the Hudson Valley:

OUR LATEST VIDEOS

Top Things To Do in Westchester and the Hudson Valley with Kids in September

Hudson Valley Hot Air Balloon Festival in Tymore Park

Union Vale
Friday, August 29-Sunday, August 31, 2025
Plan your next photo-op as some 75 hot-air balloons paint the sky in a rainbow of colors—or schedule a tethered or full flight of your own. Fireworks, helicopter rides, live music, food trucks, and family activities add to the fun at Tymore Park. READ MORE

Yorktown Grange Fair

Yorktown
Friday, September 5-Sunday, September 7, 2025
This fair, which is in its 101st year, features rides, games, food, live bands, a pro-wrestling performance, livestock competitions, animal showmanship, and fun contests like bubble gum blowing and watermelon throwing.  READ MORE

Germania Oktoberfest

Poughkeepsie
Friday, September 5-Sunday, September 7, 2025
Germania of Poughkeepsie presents this family-friendly event, featuring live German bands, Germania singers, German food, Bavarian dancers, vendors, and traditional beers for the adults. Children can enjoy games, contests, face painting, prizes, magic, and other activities. READ MORE

Flip Circus - Yorktown's Jefferson Valley Mall

Yorktown Heights
Friday, September 5-Sunday, September 7, 2025
The circus is coming to town at Cross County Center. Flip Circus highlights the enduring human spirit, with world-class clowns, acrobats, jugglers, and daredevils. See the Globe of Death Motorcycles, the Alexa Swing Pole act, and Chicago Allstars acrobats.  READ MORE

Thunderbird Farms Sunflower Festival

Pine Island
Saturday, September 6, 2025
Join Thunderbird Farms for its annual Sunflower Festival featuring karaoke, live music, a vibrant vendor market, face painting, a tie-dye station, food trucks, and much more! Stroll through the stunning sunflower field and snap photos against breathtaking backdrops. READ MORE

Chowtoberfest Music Festival

Warwick
Saturday, September 6, 2025
Enjoy live bands continuously all day plus family-friendly fun like a bounce house, face painting, a visit from a superhero, free pony rides, walks with alpacas, and a petting zoo. Don't miss the evening show with holograms and a laser light show. READ MORE

White Plains JazzFest

White Plains (some FREE)
Wednesday, September 10-Sunday, September 14, 2025
This 4-day event features numerous performances sprinkled across diverse venues (both indoors and outdoors), including Grace Church, the library plaza, Court Street, and others. Many of the performances are FREE.  READ MORE

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

Croton-on-Hudson
Opens Friday, September 12, 2025
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 2025 is a jack-o'-lantern big top adventure, a Wicked-themed, emerald-hued storybook pumpkin dreamscape, and the Headless Horseman’s Hideaway featuring spooky sips and haunting visits from the Horseman himself.  READ MORE

Mount Kisco SeptemberFest

Mount Kisco
Friday, September 12-Sunday, September 14, 2025
Mount Kisco's annual 3-day block party features a full-size carnival with rides and amusements in addition to shopping, entertainment, live music, and food. Bring a donation for the food drive and celebrate hometown heroes. Times and fees vary. READ MORE

Fall Crafts at Lyndhurst

Tarrytown
Friday, September 12-Sunday, September 14, 2025
Fall Crafts at Lyndhurst features handmade and uncommon items from 200 makers you can't find anywhere else in the county. Plus, enjoy gourmet specialties, tastings from local distilleries (new for this year: a beer truck), craft demos like wheel-thrown pottery, and family activities such as interactive puppet theater, face painting, and storytelling. READ MORE

Butterfly Day at Hudson Highlands Nature Museum

Cornwall
Saturday, September 13, 2025
Kids can get up close and personal with butterflies at this special event at the Hudson Highland Nature Center. Visit the butterfly tent; participate in a butterfly release; hear presentations about butterflies, moths, and caterpillars; and stop by the Grasshopper Grove playground.  READ MORE

Yonkers Riverfest

Yonkers–FREE
Saturday, September 13, 2025
Riverfest is the largest one-day festival in Westchester County and takes place at the Yonkers Riverfront Downtown. Enjoy inspired performances from jazz and soul to hip-hop, rock, and more, plus food, vendors, arts & crafts, rides and slides, face painting, and more. READ MORE

Armonk Cider & Donut Festival and 5K Run

Armonk–FREE
Sunday, September 14, 2025
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

Village of Monroe Cheese Festival

Monroe–FREE
Sunday, September 14, 2025
Sample artisan cheeses with live music, food trucks, and beer and wine vendors. Enjoy street performances and live bands and let your kids enjoy a free, fun-packed kid-zone!   READ MORE

Family Campout at Hudson Highlands Nature Museum

Cornwall
Friday, September 19, 2025
Bring your whole family for a night under the stars at the Hudson Highlands Nature Museum. Enjoy campfire stories, make s'mores, and if interested go for a night walk and call for owls. Enjoy a light breakfast and coffee before decamping. Help pitching tents is available. READ MORE

Hudson Valley Irish Fest

Peekskill–FREE
Saturday, September 20, 2025
Celebrate all things Irish with the Hudson River as a backdrop. Included are Irish step dancing, bands, crafts, food, and designs. A children's play area features 18th-century toys and games. A spoken-word tent and beer garden for adults enhance the day. READ MORE

Mooncake Night Market at the ArtsWestchester Gallery

White Plains
Saturday, September 20, 2025
Celebrate the magic of the full moon and autumn harvest in ArtsWestchester’s gallery with an evening of music, dance, crafts, and food. Guests can participate in hands-on workshops in Chinese calligraphy, lantern-making, mooncake stamping, decorative knotting, origami, and more. READ MORE

Cornwall Fall Festival

Cornwall
Sunday, September 21, 2025
The 51st annual fall festival returns to downtown Cornwall. Main Street is closed down and attendees can enjoy a variety of local vendors offering unique crafts, goods, and delicious food, along with live music and entertainment for all ages. The festival also features activities for children, including games and crafts. READ MORE

Fall Family Festival at Bright Horizons

Various locations
Thursday, September 25, 2025
Bright Horizons is bringing fun, friends, and family together at its fall festival. Meet other families, get to know the Bright Horizons community, and participate in hands-on fall activities. Everyone is welcome. READ MORE

Croton Oktoberfest

Croton-on-Hudson–FREE
Saturday, September 27, 2025
Croton-on-Hudson's Oktoberfest will feature live music all day and over 60 amazing food, craft beer, and local retail vendors, plus a kinder-fest for the little ones, with music, food, and fun activities to keep them entertained! READ MORE

Hudson Valley Garlic Festival in Saugerties

Saugerties
Saturday & Sunday, September 27-28, 2025
The annual two-day garlic festival in Saugerties is hugely popular for a reason. More than a foodie's paradise—with eats, demos, and more—the event also features kid-friendly attractions, such as a craft tent, live performances, and face painting. READ MORE

Places featured in this article:

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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