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20 Best Things To Do in Westchester and the Hudson Valley September 2023 with Kids

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 courtesy of the Historic Hudson Valley
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 courtesy of the Historic Hudson Valley
8/28/22 - 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, Mount Kisco Septemberfest, and the Port Jervis Fall Foliage Festival. To get in the Halloween spirit early, check out the Great Jack O'Lantern Blaze, which features more than 7,000 hand-carved and lit-up pumpkins. 

Find more top September fun in our Westchester & Hudson Valley Fall Fun Guide, including apple picking and pumpkin picking, as well as our rundown of the best fall day trips nearby. 

We’re adding more events to our Family Activity Calendar every day, so don’t forget to check it frequently.

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The Greenburgh Nature Center pulls out all the stops for a fun obstacle run near month's end. Photo courtesy of the venue
The Greenburgh Nature Center pulls out all the stops for a fun obstacle run near month's end. Photo courtesy of the venue

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

Hudson Valley Hot Air Balloon Festival

Union Vale
Friday, September 1-Sunday, September 3, 2023
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. READ MORE

Wakanda 2023

Mount Vernon–FREE
Saturday, September 2, 2023
Celebrate the heritage of Africa with an all-day festival featuring a fashion show, shopping, food, and live performances that include African dancing and drumming. Kids can also enjoy storytelling, crafts, and Black Panther character appearances. READ MORE

Yorktown Grange Fair

Yorktown
Friday, September 8-Sunday, September 10, 2023
The 99th fair features rides, games, food, live bands, circus performers, livestock competitions, animal showmanship, and assorted fun contests (think bubble gum blowing, watermelon throwing, and rubber chicken toss).  READ MORE

Germania Oktoberfest

Poughkeepsie
Friday, September 8-Sunday, September 10, 2023
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

Orange County Sweet Corn Festival

New Hampton
Sunday, September 10, 2023
The Annual Orange County Sweet Corn Festival is a day of entertainment and fun activities, including children's games, a corn maze, hayrides, a petting zoo, a corn eating contest, and more. READ MORE

White Plains JazzFest

White Plains (some FREE)
Wednesday, September 6-Sunday, September 10, 2023
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

Holy Trinity Greek Festival

New Rochelle
Thursday, September 14-Sunday, September 17, 2023
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

Family Campout

Cornwall
Friday, September 15-Saturday, September 16, 2023
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

Mount Kisco SeptemberFest

Mount Kisco
Friday, September 8-Sunday, September 10, 2023
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

The Great Jack-o'-Lantern Blaze

Croton-on-Hudson
Opens Friday, September 15, 2023
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

Fall Crafts at Lyndhurst

Tarrytown
Friday, September 9-Sunday, September 1, 2023
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

Phoenix Festival - Live Arts in Nyack

Nyack
Open Thursday, September 28, 2023
This performing arts celebration runs for 5 weekends in the fall. The performances are held outdoors in Nyack against the backdrop of majestic Hudson River vistas. Programs include live performances by the Phoenix Theatre Ensemble and Children’s Shakespeare Theatre company, as well as Rockland Symphony Orchestra concerts and a series of related special events – all in a setting a world apart from traditional performing arts venues. READ MORE

Armonk Cider & Donut Festival, 5K Run, and BHPA Fall Carnival

Armonk–FREE admission
Sunday, September 10, 2023
Enjoy a variety of activities for families and, of course, donuts and cider. A pie-eating contest, donut fishing, live music, carnival rides, kids' races, a 5K, face painting, bouncy houses, and more are featured. READ MORE

Cornwall Fall Festival

Cornwall
Sunday, September 24, 2023
The 48th annual fall festival returns to downtown Cornwall. Main Street is closed down and filled with vendors, food, and entertainment.  READ MORE

Go the Distance Walk and Family Fun Day

Valhalla–FREE
Sunday, September 24, 2023
Join hundreds of supporters, families, former patients, doctors, nurses, and workforce members in support of Maria Fareri Children’s Hospital at the “Go the Distance Walk and Family Fun Day.” A casual, 1-mile walk around Westchester Medical Center’s Valhalla campus followed by free activities including face painting, crafts, carnival games, music, character appearances, food, and more READ MORE

Walden Annual Harvest Fest

Walden–FREE
Saturday, September 30, 2023
Get ready for old-fashioned fun at this annual fall festival. Attractions include bouncy houses, a petting zoo, and a frog jumping contest. Live music and vendors add to the fun.  READ MORE

Hudson Valley Irish Fest

Peekskill–FREE
Saturday, September 23, 2023
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

Dalmatian Day 2023

Hudson–FREE
Saturday, September 23, 2023
Dalmatian Day 2023 is a family-friendly extravaganza that includes a meet-and-greet with live dalmatians, games and prizes for kids, dalmatian-themed crafts, comedy and juggling by Ray Grins, interactive safety house tours, vendor giveaways, and more.  READ MORE

Run Wild Family Forest Run and Obstacle Course

Scarsdale
Saturday, September 30-Sunday, October 1, 2023
Run Wild is a kids' forest run and obstacle course where kids can enjoy some friendly competition while getting active out in nature. Parents are encouraged to run, too. READ MORE

Port Jervis Fall Foliage Festival

Port Jervis–FREE
Sunday, September 23, 2023
Get ready for family fun at this annual street fair, with more than 100 vendors, live entertainment, a petting zoo, and more. READ MORE

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