The Metro-North lot at the Chappaqua Train Station holds cars belonging to commuters most mornings and stands mostly empty by 10 a.m., once the last express train pulls out for Grand Central. On one Saturday each fall, that same lot fills before lunch, and the overflow starts creeping onto side streets. That was the scene in 2024, during what organizers called the best-attended year in the event's eleven-year run at that point. Parking was scarce in the train station lot by late morning.
This year marks the 13th Annual Chappaqua Children's Book Festival, set for Saturday, September 26, 2026, rain or shine, at the Chappaqua Train Station. If you've lived here more than a few autumns, you already know the date belongs to the festival before you check a calendar. What's changed is the scale of what you're actually walking into, and that's worth understanding before you decide when to leave the house that morning.
From a Middle School Gym to a Commuter Lot
The festival started in 2013 as an all-volunteer, nonprofit effort founded by Dawn Greenberg, built on the idea that kids should get to meet the people behind the books they love. In its earlier years it set up at Robert E. Bell Middle School, drawing roughly 95 authors and illustrators to tables inside and around the building. That version of the event was already a nice fall tradition. It was not yet the thing it's become.
Somewhere along the way, the festival moved to the train station and kept growing until the school gym model no longer made sense. Today it spreads across the Metro-North lot itself, which is a different kind of space to fill and a different kind of crowd to manage.
The Numbers Behind the Parking Problem
By 2024, the 11th annual festival hosted more than 165 authors and illustrators, led by children's book veteran Laura Numeroff. Author Diane deGroat reportedly sold through her Halloween-themed title within the first hour and was down to a copy or two of her Thanksgiving book shortly after. That's not a detail you'd expect from a neighborhood craft fair.
By the 12th year in 2025, organizers put attendance at more than 10,000 people drawn from across the tri-state area, according to coverage in The Inside Press. That's not a Chappaqua number anymore. That's a regional one.
The festival's own site confirms something else worth noting for 2026: the application window for authors and illustrators to participate has already closed for the year, with organizers pointing hopeful applicants toward next year's cycle instead. When a volunteer-run community event has more author interest than it has tables, that tells you the demand curve has shifted well past what a hamlet of this size would produce on its own.
One returning author, Alicia Mott-Comitto of Briarcliff Manor, put it simply after a recent festival: "There's so much energy." That's the kind of line that sounds like boosterism until you've stood in that lot at 11 a.m. and felt the crowd density for yourself.
What Actually Happens on September 26
Here's the shape of the day, based on the festival's established format in recent years:
- When: Saturday, September 26, 2026, 10 a.m. to 4 p.m., rain or shine
- Where: Chappaqua Train Station, in the Metro-North commuter lot
- Cost: Free admission, free parking
- What's there: Author readings, illustrator demos, book signings, a Family Fun Zone, and gourmet food trucks
- This year's poster art: Illustrated by Jay Cooper, unveiled ahead of the festival
In recent years, food at the festival hasn't come only from trucks. The 2024 event description specifically noted that food would be available from both gourmet food trucks and the regular Chappaqua Farmers Market, which sets up at the same train station plaza every Saturday through the fall. If that pattern holds again this year, your usual Saturday market run and the book festival will share the same footprint rather than compete for it, which is one more reason the lot fills the way it does.
There's also a charitable layer that tends to get lost in the excitement over authors: the Great Chappaqua Bake Sale, which supports Share Our Strength's No Kid Hungry campaign. It's a small table next to a much bigger event, but it's been part of the festival's DNA for years.
The Practical Read, If You Actually Live Here
If your plan is to swing by around noon after brunch, know that recent years suggest the lot is already tight by then. The families who get the easy parking and the shorter lines at the popular author tables tend to be the ones who show up close to the 10 a.m. gate rather than treating it like a leisurely afternoon errand.
If you're close enough to walk or bike from the village center, this is the year to do it. You'll skip the parking math entirely and still catch the market, the food trucks, and whichever authors haven't sold out of their new titles yet.
The bigger point isn't really about parking, though the parking is the most visible symptom of it. It's that a volunteer board with no marketing department and no corporate sponsor has built, out of a commuter parking lot, one of the larger events of its kind in the country. That's not the kind of thing that shows up on a real estate listing sheet, but it's the kind of thing that tells you what a place actually is on a Saturday in late September, long after the moving trucks have left.
If you're weighing what small-town scale actually feels like day to day in Chappaqua, or thinking ahead to your own next move in New Castle or the surrounding towns, Roseanna Tedone has spent years watching these local rhythms up close. Let's Connect if you'd like to talk through what a season here really looks like before you decide anything else.
