September GoList: The Best Things to Do With Kids in Westchester

Best Things to Do with Westchester Kids in September 2018

Though September signals the closing of beaches and pools and the return to school, there are so many scheduled events this month in Westchester and the Hudson Valley, it was hard to narrow down our favorites! With fall festivals, film festivals, a book festival, a maker's festival, and non-festivals, the events this month are true standouts.

Extremely corn-y fun awaits in various forms at CORNucopia—perfect for the younger set. For sportier action, catch an equestrian competition and more at the prestigious American Gold Cup. The Chappaqua Children's Book Festival (held in October last year) is a perennial favorite, with opportunities to meet beloved authors and illustrators. 

Though Halloween might seem a ways off, trust us: You don’t want to delay snagging your tickets to The Great Jack O'Lantern Blaze, which go on sale September 4 (a moment’s delay, and you’ll wind up with a date closer to Thanksgiving). And the New York Renaissance Faire, which runs through the end of September, is worthy of a reminder after being featured in our August GoList.

Beyond these, there are many reasons to keep tabs on our Event Calendar this month, where you’ll find activities that celebrate Labor Day, the return to school, Grandparents Day, and the start of autumn, among other occasions. Stay in the know with our newsletters and check back frequently for updates.


Corn isn't just for eating at CORNucopia. Photo courtesy of the event 

CORNucopia – Sleepy Hollow
Saturday, September 1 – Monday, September 3, 2018
There’s no limit to the fun to be had with corn at this annual festival. Games, crafts, and—of course—refreshments are all truly corn-y. Pair that with 18th-century activities and you’ve got a truly a-maize-ing event! Read our in-depth review to learn more.

New York International Children’s Film Festival: Westchester – Pelham
Friday, September 7 – Tuesday, September 11, 2018
This annual film festival features curated film for kids aged 3-18 from around the world, offering the caliber of a metropolitan film house in our suburban backyards. Flicks from Latin America, retro revivals, documentaries, shorts, and more are on the schedule, as are FREE workshops and the new Wolf’s Walk Street Festival, held in conjunction.

Old New Paltz Stone House Day – New Paltz
Saturday, September 8, 2018
Set in a National Historic Landmark venue, this multicultural event pays homage to our area’s ancestors, including African, Dutch, English, Esopus Munsee, and French, with  tours of historic homes, performances, vendor demos, craftspeople, and re-enactors demonstrating musket firing, candle making, sewing, blacksmithing, and more.

Riverfest – Yonkers
Saturday, September 15, 2018
With an estimated 25,000 people expected to attend, this all-day event returns with music on multiple stages, classic cars, street performers, environmental tours, arts and crafts, and more—all FREE.

New York Air Show – New Windsor
Saturday, September 15, and Sunday, September 16, 2018
Aerial maneuvers, parachute jumps, aircraft displays, and more await you at this two-day event featuring military, civilian, and historic crafts and performers.

Go the Distance Walk and Family Fun Day – Valhalla
Sunday, September 16, 2018
This annual fundraiser features a casual one-mile walk plus family activities such as face painting, bounce houses, crafts, carnival games, The Bubble Bus, character appearances and more—all while supporting a charitable cause. Form a team or go solo. FREE

Armonk Cider & Donut Festival  Armonk
Sunday, September 23, 2018
Get your fix of fall treats at this annual festival, plus live music, a kids’ race, doughnut fishing, a carnival, and more.

Cornwall Fall Festival – Cornwall
Sunday, September 23, 2018
An abundance of kid-friendly activities will be available at this fall festival: a hay maze, pony rides, a petting zoo, animal encounters, tie-dying, and more. There will also be food and craft vendors, as well as two stages of live entertainment.

The Best of the New York International Children's Festival – Pleasantville
Sunday, September 23, 2018
Highlights of the New York International Children’s Film Festival will be presented, with screenings arranged by age group, each presenting nine international shorts.


Celebrate American Culture at Jay Day in Rye. Photo by Cutty McGill fo the Jay Heritage Society

Jay Day – Rye
Sunday, September 23, 2018
A panoply of attractions are in store at this event designed to celebrate American culture and customs. Expect live entertainment, literary events for kids, vendors, pony rides, animals, historical immersion, face painting, and more. 


The American Gold Cup is a five-day event with family-friendly attractions. 

American Gold Cup – North Salem
Wednesday, September 26 – Sunday, September 30, 2018
This prestigious equestrian event takes place over five days, with enormous prize money at stake. In addition to watching the horse-jumping events, enjoy such family-friendly attractions as pony rides, face painting, a magic show, celebrity sightings, and more (weekend only). Weekday events are FREE.


The Great Jack O'Lantern Blaze is an amazing sight, with more than 7,000 illuminated jack-o'-lanterns on display.

The Great Jack O'Lantern Blaze – Croton-on-Hudson
Various dates from September 28 through November 2018
At this wildly popular event, families can marvel at more than 7,000 hand-carved, illuminated jack-o'-lanterns displayed all over the 18th-century grounds of Van Cortlandt Manor. This event positively sells out (quickly!), so be sure to grab your tickets pronto.


Enjoy a day that's all about the love of books. Photo courtesy of Jaime Kilgore Photography

Chappaqua Children's Book Festival – Chappaqua 
Saturday, September 29, 2018
Bibliophiles can enjoy a day of kids’ activities, food, music and—of course—books! Meet popular children’s authors, enjoy readings and more. FREE admission.

In the MKNG: The Creativity Festival – Bethel
Saturday, September 29, and Sunday, September 30, 2018
Makers unite at this inaugural two-day festival in the Woodstock area. Sign up for a creative workshop, catch live music all day, shop at artisan stands, chow down, and generally be inspired in the company of creatives.

Peekskill Rotary Annual Horse Show and Country Fair – Peekskill
Saturday, September 29, and Sunday, September 30, 2018
The 48th annual horse show and fair, hosted by the Peekskill Rotary, features both English and Western riding contests and instruction throughout the day. Other family attractions include a bike rodeo, “Kountry Kitchen,” pony and hay rides, inflatables, arts and crafts, and more. Admission is free.

Be sure to check our Event Calendar for even more events happening this month and beyond in Westchester and the Hudson Valley!

Unless noted, photos by the author

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