15 Fun Things to Do in Westchester this September

Find the top things to do this month with kids in the NYC area in our Calendar of Events

Looking for things to do with kids this September in Westchester County? Our list of fun fall events includes fairs and festivals, a colorful pow wow, and more in Armonk, Cortlandt Manor, Katonah, North Salem, Peekskill, Sleepy Hollow, Tuckahoe, and beyond.


american gold cup horse show nyAmerican Gold Cup Horse Show

Old Salem Farm, North Salem
Sept. 14-15

Westchesterites who’ve never been to an equestrian show are in for a treat this year. The American Gold Cup, one of the most prestigious equestrian sporting events in the world of international show jumping, will take place Sep. 14-15 in its new home, the luxurious and historic Old Salem Farm in North Salem. Here, elite equestrian athletes, horse owners, young riding hopefuls, and enthusiastic fans will gather to enjoy this extraordinary show jumping event. Among the family friendly activities spectators can enjoy are high-end (think Hermés) boutique shopping, celebrity sightings, the signature Just World International Horseless Horse Show for kids (they do everything a horse-and-rider does, minus the horse!), and much more. The event has been designated a World Cup Qualifier competition, making it an important event for riders aspiring to compete at the 2014 World Cup Finals in Lyon, France.


painting pumpkins at fall festivalFall Fairs and Festivals

Cortlandt Manor, Katonah, Peekskill, Pleasantville, Scarsdale, Sleepy Hollow, Tarrytown
Throughout September

Even if you don’t agree that, as the old Staples commercial insisted, it’s the “most wonderful time of the year,” one thing you’ve got to give fall is its bounty of delicious tastes, visual beauty, and outdoor fun. The air is crisp, the sky seems impossibly blue, and everywhere you go, the atmosphere is alive with possibility. So load the family into the car for a short drive to one (or all!) of these delightful local fall festivals.


native american pow wowNative American Pow Wow

FDR State Park, Yorktown Heights
Sept. 21-22

The Redhawk Native American Arts Council hosts its annual Native American Pow Wow at FDR State Park Sep. 21-22. This annual full-contest pow wow attracts more than 500 Native American artists, educators, singers, dancers, storytellers, and performing groups from across the Americas. There will be more than 40 artist booths selling crafts, jewelry, food, and more, plus a live birds of prey exhibit, pony rides, a tipi raising, and the grand entry of dancers at 1pm and 4pm daily. Rain or shine.


armonk outdoor art show foot raceArmonk Outdoor Art Show and Foot Race

Foot Race: Wampus Brook Park, Maple Avenue, Armonk – Sept. 22
Art Show:
205 Business Park Drive, Armonk – Sept. 28-29

Most of Armonk comes out for the hamlet’s two big events in September: The 52nd annual Armonk Outdoor Art Show and Foot Race. The two-day, nationally recognized Art Show features 185 juried artists’ works, including oils/acrylics, watercolors, mixed media, sculpture, photography/digital art, jewelry, and fine crafts. There is free parking on site, as well as children's activities, docent tours, and a full food court.

Art Show week kicks off Sept. 22 with Jamie’s 5K Run/Walk for the Library, in memory of Jamie Love, a former member of the Byram Hills cross country and track and field teams. The race benefits the Friends of the North Castle Public Library, Inc. T-shirts are provided to the first 300 runners who sign up for either Jamie’s 5K Run/Walk or the Monet Mile Run. Prizes will be awarded.


kids making pasta in cooking classPiccoli Cuochi: Cooking Classes for Children

Westchester Italian Cultural Center, Tuckahoe
Sept. 28

Piccoli Cuochi means “Little Chefs.” And in Piccoli Cuochi: Cooking Classes for Children at the Westchester Italian Cultural Center, little chefs get to enjoy a fun, hands-on workshop that will teach them how to prepare fettuccine tricolore. Participants will make this delicious pasta from scratch and take home what they make. A plate of homemade fettucine dressed with different sauces will be served at the end of the class. Space is limited; early registration is suggested. Participants must register and prepay.


museum day liveMuseum Day Live!

Participating museums in Westchester and across the U.S.
Sept. 28

Did you know the best free ticket in town is just a click away? Smithsonian magazine’s ninth annual Museum Day Live! grants free admission to participating museums for two people per household on Sept. 28. More than 800 museums and cultural institutions nationwide will be emulating the Washington, DC-based Smithsonian Institution’s free admission policy for one day. Online ticketing makes it easy to gain access to the institution of your choice, excluding parking and special events and exhibits. Visit smithsonian.com/museumdaylive to see a list of 2013 participating museums and print your official Museum Day Live! ticket. Among the participating institutions in our area: Katonah Museum of Art (Katonah), Bartow-Pell Mansion Museum (Bronx), and Hudson Valley Center for Contemporary Art (Peekskill). Check smithsonian.com/museumdaylive for updates.

More Fun

Find where to pick your own apples in New York, New Jersey, and Connecticut

Search our full calendar of events for even more fun family activities in the NYC area